The Real Donald Trump Is a Character on TV

Understand that, and you’ll understand what he’s doing in the White House.

On Sept. 1, with a Category 5 hurricane off the Atlantic coast, an angry wind was issuing from the direction of President Trump’s Twitter account. The apparent emergency: Debra Messing, the co-star of “Will & Grace,” had tweeted that “the public has a right to know” who is attending a Beverly Hills fund-raiser for Mr. Trump’s re-election.

“I have not forgotten that when it was announced that I was going to do The Apprentice, and when it then became a big hit, Helping NBC’s failed lineup greatly, @DebraMessing came up to me at an Upfront & profusely thanked me, even calling me ‘Sir,’ ” wrote the 45th president of the United States.

It was a classic Trumpian ragetweet: aggrieved over a minor slight, possibly prompted by a Fox News segment, unverifiable — he has a long history of questionable tales involving someone calling him “Sir” — and nostalgic for his primetime-TV heyday. (By Thursday he was lashing Ms. Messing again, as Hurricane Dorian was lashing the Carolinas.)

This is a futile effort. Try to understand Donald Trump as a person with psychology and strategy and motivation, and you will inevitably spiral into confusion and covfefe. The key is to remember that Donald Trump is not a person. He’s a TV character.

I mean, O.K., there is an actual person named Donald John Trump, with a human body and a childhood and formative experiences that theoretically a biographer or therapist might usefully delve into someday. (We can only speculate about the latter; Mr. Trump has boasted on Twitter of never having seen a psychiatrist, preferring the therapeutic effects of “hit[ting] ‘sleazebags’ back.”)

But that Donald Trump is of limited significance to America and the world. The “Donald Trump” who got elected president, who has strutted and fretted across the small screen since the 1980s, is a decades-long media performance. To understand him, you need to approach him less like a psychologist and more like a TV critic.

He was born in 1946, at the same time that American broadcast TV was being born. He grew up with it. His father, Fred, had one of the first color TV sets in Jamaica Estates. In “The Art of the Deal” Donald Trump recalls his mother, Mary Anne, spending a day in front of the tube, enraptured by the coronation of Queen Elizabeth in 1953. (“For Christ’s sake, Mary,” he remembers his father saying, “Enough is enough, turn it off. They’re all a bunch of con artists.”)

TV was his soul mate. It was like him. It was packed with the razzle-dazzle and action and violence that captivated him. He dreamed of going to Hollywood, then he shelved those dreams in favor of his father’s business and vowed, according to the book “TrumpNation” by Timothy O’Brien, to “put show business into real estate.”

As TV evolved from the homogeneous three-network mass medium of the mid-20th century to the polarized zillion-channel era of cable-news fisticuffs and reality shocker-tainment, he evolved with it. In the 1980s, he built a media profile as an insouciant, high-living apex predator. In 1990, he described his yacht and gilded buildings to Playboy as “Props for the show … The show is ‘Trump’ and it is sold-out performances everywhere.”

He syndicated that show to Oprah, Letterman, NBC, WrestleMania and Fox News. Everything he achieved, he achieved by using TV as a magnifying glass, to make himself appear bigger than he was.

He was able to do this because he thought like a TV camera. He knew what TV wanted, what stimulated its nerve endings. In his campaign rallies, he would tell The Washington Post, he knew just what to say “to keep the red light on”: that is, the light on a TV camera that showed that it was running, that you mattered. Bomb the [redacted] out of them! I’d like to punch him in the face! The red light radiated its approval. Cable news aired the rallies start to finish. For all practical purposes, he and the camera shared the same brain.

Even when he adopted social media, he used it like TV. First, he used it like a celebrity, to broadcast himself, his first tweet in 2009 promoting a “Late Show With David Letterman” appearance. Then he used it like an instigator, tweeting his birther conspiracies before he would talk about them on Fox News, road-testing his call for a border wall during the cable-news fueled Ebola and border panics of the 2014 midterms.

When he was a candidate, and especially when he was president, his tweets programmed TV and were amplified by it. On CNBC, a “BREAKING NEWS: TRUMP TWEET” graphic would spin out onscreen as soon as the words left his thumbs. He would watch Fox News, or Lou Dobbs, or CNN or “Morning Joe” or “Saturday Night Live” (“I don’t watch”), and get mad, and tweet. Then the tweets would become TV, and he would watch it, and tweet again.

If you want to understand what President Trump will do in any situation, then, it’s more helpful to ask: What would TV do? What does TV want?

It wants conflict. It wants excitement. If there is something that can blow up, it should blow up. It wants a fight. It wants more. It is always eating and never full.

Some presidential figure-outers, trying to understand the celebrity president through a template that they were already familiar with, have compared him with Ronald Reagan: a “master showman” cannily playing a “role.”

The comparison is understandable, but it’s wrong. Presidents Reagan and Trump were both entertainers who applied their acts to politics. But there’s a crucial difference between what “playing a character” means in the movies and what it means on reality TV.

Ronald Reagan was an actor. Actors need to believe deeply in the authenticity and interiority of people besides themselves — so deeply that they can subordinate their personalities to “people” who are merely lines on a script. Acting, Reagan told his biographer Lou Cannon, had taught him “to understand the feelings and motivations of others.”

Being a reality star, on the other hand, as Donald Trump was on “The Apprentice,” is also a kind of performance, but one that’s antithetical to movie acting. Playing a character on reality TV means being yourself, but bigger and louder.

Reality TV, writ broadly, goes back to Allen Funt’s “Candid Camera,” the PBS documentary “An American Family,” and MTV’s “The Real World.” But the first mass-market reality TV star was Richard Hatch, the winner of the first season of “Survivor” — produced by Mark Burnett, the eventual impresario of “The Apprentice”— in the summer of 2000.

Mr. Hatch won that first season in much the way that Mr. Trump would run his 2016 campaign. He realized that the only rules were that there were no rules. He lied and backstabbed and took advantage of loopholes, and he argued — with a telegenic brashness — that this made him smart. This was a crooked game in a crooked world, he argued to a final jury of players he’d betrayed and deceived. But, hey: At least he was open about it!

While shooting that first season, the show’s crew was rooting for Rudy Boesch, a 72-year-old former Navy SEAL and model of hard work and fair play. “The only outcome nobody wanted was Richard Hatch winning,” the host, Jeff Probst, would say later. It “would be a disaster.” After all, decades of TV cop shows had taught executives the iron rule that the viewers needed the good guy to win.

But they didn’t. “Survivor” was addictively entertaining, and audiences loved-to-hate the wryly devious Richard the way they did Tony Soprano and, before him, J.R. Ewing. More than 50 million people watched the first-season finale, and “Survivor” has been on the air nearly two decades.

From Richard Hatch, we got a steady stream of Real Housewives, Kardashians, nasty judges, dating-show contestants who “didn’t come here to make friends” and, of course, Donald Trump.

Reality TV has often gotten a raw deal from critics. (Full disclosure: I still watch “Survivor.”) Its audiences, often dismissed as dupes, are just as capable of watching with a critical eye as the fans of prestige cable dramas. But when you apply its mind-set — the law of the TV jungle — to public life, things get ugly.

In reality TV — at least competition reality shows like “The Apprentice” — you do not attempt to understand other people, except as obstacles or objects. To try to imagine what it is like to be a person other than yourself (what, in ordinary, off-camera life, we call “empathy”) is a liability. It’s a distraction that you have to tune out in order to project your fullest you.

Reality TV instead encourages “getting real.” On MTV’s progressive, diverse “Real World,” the phrase implied that people in the show were more authentic than characters on scripted TV — or even than real people in your own life, who were socially conditioned to “be polite.” But “getting real” would also resonate with a rising conservative notion: that political correctness kept people from saying what was really on their minds.

Being real is not the same thing as being honest. To be real is to be the most entertaining, provocative form of yourself. It is to say what you want, without caring whether your words are kind or responsible — or true — but only whether you want to say them. It is to foreground the parts of your personality (aggression, cockiness, prejudice) that will focus the red light on you, and unleash them like weapons.

Maybe the best definition of being real came from the former “Apprentice” contestant and White House aide Omarosa Manigault Newman in her memoir, “Unhinged.” Mr. Trump, she said, encouraged people in his entourage to “exaggerate the unique part of themselves.” When you’re being real, there is no difference between impulse and strategy, because the “strategy” is to do what feels good.

This is why it misses a key point to ask, as Vanity Fair recently did after Mr. Trump’s assault on Representative Elijah E. Cummings and the city of Baltimore in July, “Is the president a racist, or does he just play one on TV?” In reality TV, if you are a racist — and reality TV has had many racists, like Katie Hopkins, the far-right British “Apprentice” star the president frequently retweets — then you are a racist and you play one on TV.

So if you actually want a glimpse into the mind of Donald J. Trump, don’t look for a White House tell-all or some secret childhood heartbreak. Go to the streaming service Tubi, where his 14 seasonsof “The Apprentice” recently became accessible to the public.

You can fast-forward past the team challenges and the stagey visits to Trump-branded properties. They’re useful in their own way, as a picture of how Mr. Burnett buttressed the future president’s Potemkin-zillionaire image. But the unadulterated, 200-proof Donald Trump is found in the boardroom segments, at the end of each episode, in which he “fires” one contestant.

In theory, the boardroom is where the best performers in the week’s challenges are rewarded and the screw-ups punished. In reality, the boardroom is a new game, the real game, a free-for-all in which contestants compete to throw one another under the bus and beg Mr. Trump for mercy.

There is no morality in the boardroom. There is no fair and unfair in the boardroom. There is only the individual, trying to impress Mr. Trump, to flatter Mr. Trump, to commune with his mind and anticipate his whims and fits of pique. Candidates are fired for

  • being too nice to their adversaries (weak), for
  • giving credit to their teammates, for
  • interrupting him.

The host’s decisions were often so mercurial, producers have said, that they would have to go back and edit the episodes to impose some appearance of logic on them.

What saves you in the boardroom? Fighting. Boardroom Trump loves to see people fight each other. He perks up at it like a cat hearing a can opener. He loves to watch people scrap for his favor (as they eventually would in his White House). He loves asking contestants to rat out their teammates and watching them squirm with conflict. The unity of the team gives way to disunity, which in the Trumpian worldview is the most productive state of being.

 

And America loved boardroom Trump — for a while. He delivered his catchphrase in TV cameos and slapped it on a reissue of his 1980s Monopoly knockoff Trump: The Game. (“I’m back and you’re fired!”) But after the first season, the ratings dropped; by season four they were nearly half what they were in season one.

He reacted to his declining numbers by ratcheting up what worked before: becoming a louder, more extreme, more abrasive version of himself. He gets more insulting in the boardroom — “You hang out with losers and you become a loser”— and executes double and quadruple firings.

It’s a pattern that we see as he advances toward his re-election campaign, with an eye not on the Nielsen ratings but on the polls: The only solution for any given problem was a Trumpier Trump.

Did it work for “The Apprentice”? Yes and no. His show hung on to a loyal base through 14 seasons, including the increasingly farcical celebrity version. But it never dominated its competition again, losing out, despite his denials, to the likes of the sitcom “Mike & Molly.”

Donald Trump’s “Apprentice” boardroom closed for business on Feb. 16, 2015, precisely four months before he announced his successful campaign for president. And also, it never closed. It expanded. It broke the fourth wall. We live inside it now.

Now, Mr. Trump re-creates the boardroom’s helter-skelter atmosphere every time he opens his mouth or his Twitter app. In place of the essentially dead White House press briefing, he walks out to the lawn in the morning and reporters gaggle around him like “Apprentice” contestants awaiting the day’s task. He rails and complains and establishes the plot points for that day’s episode:

  • Greenland!
  • Jews!
  • “I am the chosen one!”

Then cable news spends morning to midnight happily masticating the fresh batch of outrages before memory-wiping itself to prepare for tomorrow’s episode. Maybe this sounds like a TV critic’s overextended metaphor, but it’s also the president’s: As The Times has reported, before taking office, he told aides to think of every day as “an episode in a television show in which he vanquishes rivals.”

Mr. Trump has been playing himself instinctually as a character since the 1980s; it’s allowed him to maintain a profile even through bankruptcies and humiliations. But it’s also why, on the rare occasions he’s had to publicly attempt a role contrary to his naturecalling for healing from a script after a mass shooting, for instance — he sounds as stagey and inauthentic as an unrehearsed amateur doing a sitcom cameo.

His character shorthand is “Donald Trump, Fighter Guy Who Wins.” Plop him in front of a camera with an infant orphaned in a mass murder, and he does not have it in his performer’s tool kit to do anything other than smile unnervingly and give a fat thumbs-up.

This is what was lost on commentators who kept hoping wanly that this State of the Union or that tragedy would be the moment he finally became “presidential.” It was lost on journalists who felt obligated to act as though every modulated speech from a teleprompter might, this time, be sincere.

The institution of the office is not changing Donald Trump, because he is already in the sway of another institution. He is governed not by the truisms of past politics but by the imperative of reality TV: never de-escalate and never turn the volume down.

This conveniently echoes the mantra he learned from his early mentor, Roy Cohn: Always attack and never apologize. He serves up one “most shocking episode ever” after another, mining uglier pieces of his core each time: progressing from profanity about Haiti and Africa in private to publicly telling four minority American congresswomen, only one of whom was born outside the United States, to “go back” to the countries they came from.

  • The taunting.
  • The insults.
  • The dog whistles.
  • The dog bullhorns.
  • The “Lock her up” and “Send her back.”

All of it follows reality-TV rules. Every season has to top the last. Every fight is necessary, be it against Ilhan Omar or Debra Messing. Every twist must be more shocking, every conflict more vicious, lest the red light grow bored and wink off. The only difference: Now there’s no Mark Burnett to impose retroactive logic on the chaos, only press secretaries, pundits and Mike Pence.

To ask whether any of this is “instinct” or “strategy” is a parlor game. If you think like a TV camera — if thinking in those reflexive microbursts of adrenaline and testosterone has served you your whole life — then the instinct is the strategy.

And to ask who the “real” Donald Trump is, is to ignore the obvious. You already know who Donald Trump is. All the evidence you need is right there on your screen. He’s half-man, half-TV, with a camera for an eye that is constantly focused on itself. The red light is pulsing, 24/7, and it does not appear to have an off switch.

John Bolton on the Warpath

Can Trump’s national-security adviser sell the isolationist President on military force?

Bolton graduated from law school as the Reagan revolution was taking shape. He moved to Washington, joined the law firm of Covington & Burling, and immersed himself in the conservative cause. Bolton was active in a series of conflicts that helped define the battleground of contemporary politics. He worked as Ralph Winter’s assistant and, while still in his twenties, was involved  in guiding a landmark federal lawsuit, Buckley v. Valeo, to the Supreme Court. Winter and Bolton made the case that strict limits on campaign spending violated the right to free speech. They won, and the decision helped release a flood of private money into the American political system. In 1985, Bolton joined the Reagan Justice Department; there, he helped shepherd the Supreme Court nomination of Robert Bork, whose ultimately unsuccessful bid began the era of fiercely partisan high-court nominations. During the contested Presidential election of 2000, Bolton flew to Florida to help insure that George W. Bush secured the office. In his memoir, he notes, with only slight embarrassment, that Republican colleagues called him “the Atticus Finch of Palm Beach County.”

.. Dick Cheney, the Vice-President, urged an assertive use of military power abroad, while Colin Powell, the Secretary of State, was more restrained. Lawrence Wilkerson, Powell’s chief of staff, told me that Bolton was appointed to his position only at Cheney’s insistence. “Everyone knew that Bolton was Cheney’s spy,”
.. Bolton told the group, “I don’t care about Syria, but I do care about Iran.” He said that the American forces would stay in Syria until the Iranians left—potentially for years. Bolton told his aides to communicate the new policy to the Russians, and he declared it publicly in September, 2018.
.. Richard Armitage, the Deputy Secretary of State, took Bolton aside and “told him to shut up,” Wilkerson said. Before Bolton testified to Congress, much of his language was diluted. Armitage reached out to a team of intelligence officers who vetted public statements made by State Department officials, and asked them to give special scrutiny to Bolton’s. “Nothing Bolton said could leave the building until I O.K.’d it,” Thomas Fingar, who led the team at the time, told me.

.. As the Bush White House made the case to invade Iraq, Bolton came into conflict with José Bustani, who was in charge of overseeing the Chemical Weapons Convention—a treaty, endorsed by the U.S. and a hundred and ninety-two other countries, that bans the production of chemical weapons. Bustani, a former senior diplomat from Brazil, was negotiating with the Iraqi government to adopt the treaty, which mandated immediate inspections by outside technicians. He thought that, if inspectors could verify that Iraq had abandoned its chemical-weapons program, an invasion wouldn’t be necessary. But, he told me, when the Iraqis agreed to accept the convention, the Bush Administration asked him to halt his negotiations. “I think the White House was worried that if I succeeded it would mess up their plans to invade,” he said.

Not long afterward, Bustani recalls, Bolton showed up at his office in The Hague and demanded that he resign. When Bustani refused, Bolton said, “We know you have two sons in New York. We know your daughter is in London. We know where your wife is.” (Bolton has denied this.) Bustani held firm, and the White House, determined to remove him, convened an extraordinary session of the Convention’s members—in many cases, Bustani said, paying the travel expenses of delegates to insure that they attended. The group voted forty-eight to seven, with forty-three abstentions, to cut short Bustani’s term.

Later that year, Bustani was nominated for the Nobel Peace Prize, for his work against chemical weapons. When U.S. troops moved into Iraq, they found no evidence of weapons of mass destruction. Commentators across the political spectrum have decried the invasion—even Trump calls it “a big, fat mistake”—but Bolton hasn’t changed his view. In 2015, he told the Washington Examiner, “I still think the decision to overthrow Saddam was correct.”

 

.. In March, 2005, Bush nominated Bolton to be the Ambassador to the United Nations, a move that was widely seen as an expression of contempt for the institution. Bolton had a history of deriding the U.N., once saying that if the headquarters “lost ten stories, it wouldn’t make a bit of difference.”

Still, Democrats in the Senate anticipated a routine hearing; they were the minority party and could do little to resist. Tony Blinken, who was the staff director of the Senate Foreign Relations Committee, told me that the members began to reconsider as they examined Bolton’s work in the State Department. “We saw a pattern of Mr. Bolton trying to manipulate intelligence to justify his views,” Blinken told me. “If it had happened once, maybe. But it came up multiple times, and always it was the same underlying issue: he would stake out a position, and then, if the intelligence didn’t support it, he would try to exaggerate the intelligence and marginalize the officials who had produced it.” After several days of testimony, Senator George Voinovich, a Republican from Ohio, declared, “John Bolton is the poster child of what someone in the diplomatic corps should not be.”

The committee declined to advance Bolton’s nomination, but Bush moved ahead anyway, sending him to the U.N. on a “recess appointment,” a temporary assignment made when the Senate is out of session. His old friend Clarence Thomas swore him in. Bolton’s associates from that time told me that he refrained from ordinary diplomatic niceties: he did not engage in small talk, linger at cocktail parties, or attend national commemorations. Not long after Bolton took the job, Bush visited him in New York. “Are you having fun?” Bush asked. “It’s a target-rich environment,” Bolton replied.

In “Surrender Is Not an Option,” Bolton gives a minute-by-minute accounting of his time at the U.N., describing both foes and allies in strikingly undiplomatic language. He refers to “EUroids,” the European diplomats whom he generally regarded as soft on America’s enemies; to “the Crusaders of Compromise,” as he describes the national-security establishment; and to “the True Believers and the High Minded.” He even derides the U.K., traditionally America’s closest ally. “Many Brits believed that their role in life was to play Athens to America’s Rome, lending us the benefit of their superior suaveness, and smoothing off our regrettable colonial rough edges,” Bolton writes.

Bolton built a reputation for being abrasive but knowledgeable, with tremendous powers of recall. A U.S. diplomat told me that he once walked into Bolton’s office at the U.N. to ask about an issue concerning Somalia. Bolton replied by quoting, verbatim, from a memo written during the Reagan Administration, some twenty years before. “As John’s talking about it, I can see his eyes moving back and forth like he’s reading the memo—he was reading it from memory,” the diplomat told me.

.. Colleagues from other countries struggled to accommodate him. “On a personal basis, you can joke with him,” the Western diplomat who knows Bolton told me. Working with him was a different story: “Coöperation was possible, but very much on his conditions.” Bolton had spent decades refining an argument that multilateral institutions and international agreements often did more harm than good—that each one represented a loss of American sovereignty. “Bolton has a Hobbesian view of the universe—life is nasty, brutish, and short,” the former American official who worked with Bolton told me. “There are a lot of nasty people out there who want to do us harm. If our country’s interests align with another’s, it’s a fleeting phenomenon, and the moment our interests diverge they will sell us down the river.” Bolton doesn’t ordinarily concern himself with the internal affairs of other nations, or with trying to democratize them, the former official said: “The U.S. has values domestically, but he doesn’t give a shit about the values of others. If it advances your interests to work with another country, then do it.

Bolton had some successes at the U.N. Most notably, he helped persuade the Security Council to impose its first economic sanctions on North Korea for its nuclear-weapons programs. But when his post expired, after sixteen months, the Democrats had won back the majority in Congress, and it was clear that Bolton would not be confirmed. On December 31, 2006, he stepped down.

.. A few months later, Bolton appeared on Fox News to warn viewers that their government was intolerably complacent. “Six years after 9/11, people are simply not focussing the way they should,” he said. “I hope it is not going to take another 9/11 to wake us up—particularly not a 9/11 with weapons of mass destruction.” Bolton, for years a favored guest on Fox, became a paid commentator. During the next decade, he made hundreds of appearances, often arguing that America needed to act urgently to counter threats from abroad. He spoke in favor of military strikes on Iranian training camps (“This is not provocative or preëmptive—this is entirely responsive”), forced regime change in North Korea (“the only solution”), and punitive measures against Vladimir Putin for sheltering the intelligence leaker Edward Snowden (“We need to do things that cause him pain”).

After decades of public-sector work, Bolton grew rich in the private sector. According to a financial disclosure that he filed before joining Trump’s Administration, he made at least two million dollars in 2017, including some six hundred thousand from Fox; two hundred and fifty thousand from the American Enterprise Institute, where he was a senior fellow; and a hundred and twenty thousand from Rhône Group, a private-equity firm. In the course of ten years, Bolton wrote at least six hundred newspaper articles, and the uncompromising beliefs that had piqued colleagues in government found a willing audience outside it. After the Bush Administration reduced sanctions on North Korea, he wrote, in an op-ed, “Nothing can erase the ineffable sadness of an American presidency, like this one, in total intellectual collapse.” When Bush was asked about it, he said, “I don’t consider Bolton credible,” and lamented spending political capital on him. The Obama Administration and its diplomatic efforts in the Middle East inspired even greater scorn. Following Obama’s acceptance speech for the 2009 Nobel Peace Prize, which Bolton criticized as “turgid,” “repetitive,” and “high-school level,” he dismissed the President as fundamentally naïve. Homo sapiens are hardwired for violent conflict,” he said. “We’re not going to eliminate violent conflict until Homo sapiens ceases to exist as a separate species.” Later, he wrote a book-length jeremiad about international law titled “How Barack Obama Is Endangering Our National Sovereignty.”

.. Bolton found an especially enthusiastic reception for arguments about the dangers of Islam. From 2013 to 2018, he was the chairman of the Gatestone Institute, which describes itself as “dedicated to educating the public about what the mainstream media fails to report.” The institute, which paid Bolton a hundred and fifty-five thousand dollars in 2017, has published virulently anti-Muslim articles of questionable accuracy. During Bolton’s tenure, one article warned of an impending “jihadist takeover” of Europe, and another claimed that immigrants from Somalia and other countries were turning Sweden into the “rape capital of the West.” A report titled “History of the Muslim Brotherhood Penetration of the U.S. Government” suggested that both the anti-tax activist Grover Norquist and the State Department official Huma Abedin were sleeper agents. According to a database maintained by NBC News, at least four articles published by Gatestone were retweeted by the Internet Research Agency, the Russian intelligence front that led efforts to sow dissension during the 2016 election.

Like many conservatives in Israel and in the U.S., Bolton rejects the idea of a two-state solution. At a speech in Israel in 2017, he instead advocated a “three-state solution,” in which Israel, Jordan, and Egypt would divide up the Palestinian territories in Gaza and the West Bank, abolishing the political entities that now exist there. For that speech, Bolton received a hundred thousand dollars and a Guardian of Zion Award from Bar-Ilan University.

As Bolton became a celebrity in conservative media, he used his visibility to establish himself in electoral politics. In 2013, he set up a political-action committee, John Bolton Super pac, which raised money to support Republican candidates. The most significant donor was Robert Mercer, the right-wing activist, hedge-fund billionaire, and co-founder of the data firm Cambridge Analytica, which later became notorious for capturing private information from some eighty-seven million Facebook users. Mercer gave the super pac a total of five million dollars. During the elections in 2014 and 2016, Bolton’s organization paid Cambridge Analytica $1.2 million, for psychographic data to tailor messages that would help Senate candidates, including Scott Brown, in New Hampshire, and Thom Tillis, in North Carolina. But Groombridge, Bolton’s former aide, told me that the data turned out to be less effective than promised. “It was useless,” he said. “We used it the way they told us, and it had no discernible impact whatsoever.”

.. After forming the pac, Bolton briefly considered running for President, but people close to him said that he was more focussed on another job. “He was running for Secretary of State,” Groombridge told me. As with Bolton’s nomination for U.N. Ambassador, there were reasons for concern that he wouldn’t pass Senate confirmation. In Bolton’s financial disclosure, he listed a forty-thousand-dollar payment, for a speech that he gave, in 2016, to Mujahideen-e-Khalq, an Iranian exile group dedicated to overthrowing the government in Tehran. The M.E.K., which professes an eccentric variant of Islam, has been characterized by many experts as resembling a cult. From 1997 until 2012, the United States listed it as a terrorist group, owing to a campaign of bombings and assassinations that it led in Iran. Bolton’s association with the group apparently went back at least to that time. During the speech in 2016, he told the crowd, “I just say again what I have been saying for ten years that I’ve been coming to this rally: the regime in Tehran needs to be overthrown at the earliest opportunity!”

Karim Sadjadpour, an Iran expert at the Carnegie Endowment for International Peace and a frequent critic of the regime, said that Bolton’s relationship with the group should have disqualified him from senior government jobs. “Anyone who pimps himself out to the M.E.K. fails the litmus test for integrity,” he said.

In 2011, Bolton became the head of the National Rifle Association’s international-affairs subcommittee. Two years later, he gave a video address to a conference hosted by a Russian gun-rights group, the Right to Bear Arms. In it, Bolton offered congratulations on the twentieth anniversary of the Russian constitution, which, he said, “signalled a new era of freedom for the Russian people and created a new force for democracy in the world.”

The conference appears to have been connected with the Kremlin’s campaign to influence politically powerful groups in the United States. It was organized by Maria Butina, who was recently sentenced to eighteen months in prison for conspiracy, after attempting to infiltrate the N.R.A. on behalf of the Russian government. Butina worked closely on the Right to Bear Arms with Alexander Torshin, a politician and an associate of Putin’s with links to organized crime. Last May, three days before Bolton became the national-security adviser, the Treasury Department imposed sanctions on Torshin, barring him from the Western financial system.

Bolton’s disclosure also listed payments, totalling a hundred and fifteen thousand dollars, from a foundation controlled by Viktor Pinchuk, a Ukrainian oligarch. Pinchuk presents his foundation as a forum for diverse views, but his allegiances are murky. In 2012, he reportedly paid Gregory Craig, a former counsel for the Obama White House, to write a report intended to exonerate Ukraine’s pro-Russian President for jailing his chief opponent. (Pinchuk denies this.) Craig is now under indictment for lying about the matter to investigators working for the special counsel Robert Mueller. (Bolton’s connections later inspired questions about whether he posed a security risk. In March, 2019, Tricia Newbold, a White House personnel officer, testified that Trump had given security clearances to twenty-five White House officials who had failed to pass background checks. The names of those people were not released, but, after the news broke, the House Oversight Committee asked to see Bolton’s personnel files, along with those of several others.)

In his bid for Secretary of State, Bolton had support from populist conservatives. According to a former senior Administration adviser, the Mercer family “pushed hard for him.” But his candidacy was derailed by members of the Republican establishment. Robert M. Gates, the former Secretary of Defense, and Condoleezza Rice, the former Secretary of State, suggested that Trump appoint Rex Tillerson, an oil C.E.O. with experience in international business. “I wanted to recommend someone who would be good,” Gates told me. Tillerson got the job.

One weekend in 2017, Bolton and General H. R. McMaster were invited to Mar-a-Lago, the President’s Palm Beach mansion, to audition to become national-security adviser. McMaster won. A decorated veteran of the wars in Iraq and Afghanistan with a reputation as an iconoclast, he came to Mar-a-Lago in full-dress uniform. According to the former senior Administration adviser, McMaster had support from Jared Kushner, who thought that his appointment would play well in the press. Trump admired Bolton’s Fox appearances—he has praised him as “a tough cookie.” But the former senior Administration adviser told me that Trump, who prefers that his officials look the part, was put off by Bolton’s mustache—and, more significant, by his interventionist mind-set. “Trump had big reservations,” the official said. “John wants to bomb everyone.”

If Bolton was disappointed at being passed over, McMaster’s experience in the White House might have reassured him. McMaster was sorely out of place: a seasoned navigator of international institutions working for a President who often seemed determined to tear them down. The chemistry between McMaster and Trump was never good. “H.R. is intense, and he would try to tell the President as best he could the consequences of his decisions,” a former senior Administration official told me.

McMaster also clashed with Secretary of Defense James Mattis. On numerous occasions, current and former officials say, Mattis tried to block White House initiatives, leaving McMaster caught in the middle. In the fall of 2017, McMaster was planning a private session to develop military options for the possibility of conflict with North Korea: a war game, with Trump in attendance, at the Presidential retreat in Camp David. McMaster asked Mattis to send officers and planners. Mattis ignored him. “He prevented the thing from happening,” the former senior Administration official told me. Later, Mattis kept General John Nicholson, the commander of American forces in Afghanistan, from meeting with Trump.

 

Administration officials speculate that Mattis was trying to avoid a war, or that he simply wanted to control the flow of information, so that the President could not make ill-advised decisions. “There are a lot of people in the Administration who want to limit the President’s options because they don’t want the President to get anything done,” the former senior Administration official told me.

Mattis declined to comment for the record, but a former senior national-security official told me, without confirming any incidents, that a strategy had evolved. “The President thinks out loud,” he said. “Do you treat it like an order? Or do you treat it as part of a longer conversation? We treated it as part of a longer conversation.” By allowing Trump to talk without acting, he said, “we prevented a lot of bad things from happening.” In 2017, Mattis and his staff helped forestall a complete withdrawal of American forces from both Afghanistan and Syria.

McMaster also acquired enemies outside the White House. Mort Klein, the head of the Zionist Organization of America, told me he believed that McMaster was “hostile to Israel,” citing offenses that ranged from advocating “Palestinian self-determination” to dodging a question about whether the Western Wall is in Israeli territory. Klein began a quiet campaign against McMaster, with help from Sheldon Adelson, the Republican casino magnate, and Safra Catz, the C.E.O. of Oracle, both of whom are fervent supporters of the Israeli right wing. “We were pushing for him to be fired,” Klein told me. For Klein and his allies, Bolton’s politics were more appealing. He has deep connections to the Israeli national-security establishment and to Prime Minister Benjamin Netanyahu. In 2018, he gave a well-compensated speech to the Friends of the Israel Defense Forces. “John almost regards Israel as part of the United States,” the former official who worked with Bolton told me. “He thinks our interests and their interest are identical.”

.. In March, 2018, according to a former Administration official, the President called McMaster and asked what he would think if Bolton became the new national-security adviser. It was clear to McMaster that he was being fired, but less clear that the President was certain Bolton was the right replacement. The official, who overheard Trump’s side of the conversation, recalled that the President ended the call with an uncomfortable joke: “Bolton is a hawk like you. He’s going to get us into a war.”

When Bolton took over, he quickly demonstrated an unsentimental style: he told Trump that he could not work with McMaster’s former aide Keith Kellogg, a seventy-three-year-old veteran who had won a Silver Star in Vietnam. Trump decided to send Kellogg to work for Vice-President Mike Pence. The former senior Administration official told me that there was widespread sympathy for Bolton: “Kellogg doesn’t have all of his faculties. He’s like the crazy uncle at Thanksgiving. But Trump liked him, so Pence had to take him.”

McMaster had set up a rigorous process for discussing issues with staff members, making recommendations to the President, and disseminating decisions through the bureaucracy. Under Bolton, there are fewer meetings, less collaboration; he often disappears into his office to immerse himself in documents. “H.R.’s door was always open—Bolton’s is closed,” a former national-security official told me. “He reads the memos. There just isn’t a lot of feedback.” Some former officials believe that Bolton’s insularity could be dangerous, particularly in a crisis, when various arms of the government and the military have to mount a quick and coördinated response. “It’s chaos under Bolton,” the former senior national-security official told me. “The national-security adviser is supposed to facilitate the President’s directives and coördinate national policy among the various government agencies. That process has completely broken down.” The official added, “Bolton hasn’t set any priorities. No one knows what the policies are—what’s important, what’s less important. The head is not connected to the body.” Principals’ meetings—crucial gatherings involving the President, the Joint Chiefs of Staff, and the heads of intelligence agencies—have become rare. “I don’t remember the last time there was a fucking principals’ meeting,” the official said.

When I raised the issue with Bolton, he seemed unconcerned. He pointed to an oil painting on his office wall which depicted George H. W. Bush with a small group of close aides, including Brent Scowcroft, his national-security adviser. “That’s decision-making,” he said.

.. The comparison to the first Bush Administration doesn’t go far. Scowcroft and Bush were temperamentally similar—both reflective, cautious members of the establishment. Trump is restless and impulsive; Bolton, who goes to bed at nine-thirty every night and rises at three-thirty in the morning, is known for his lawyerly focus. Scowcroft and Bush were close friends before they began working together; Trump and Bolton were only vaguely acquainted. As national-security adviser, Bolton has unrivalled proximity to the Commander-in-Chief. But he described their relationship as businesslike. “I don’t socialize with the President, I don’t play golf with him—I see him in the morning and I talk to him at night,” he told me. In addition to giving Trump a rundown of potential national threats each morning, Bolton attends the President’s Daily Brief, a top-secret meeting with Gina Haspel, the head of the C.I.A., and Dan Coats, the director of National Intelligence. Trump prefers to hold these meetings just two or three times a week, and is famously susceptible to distractions—people walking into the office, telephone calls, even houseflies. Aides have found that detailed briefings provoke impatience; graphics and bullet points work better, and relatable photographs better still. “Bolton gets to the point very fast,” a senior Administration official told me. “He’s very brief, and the President appreciates that.” Groombridge, the former aide, said, “John is thinking, To the extent I can modify or mollify the President’s actions, I will. He is truly a patriot. But I wonder how he goes into work every day, because deep in his heart he believes the President is a moron.”

Trump’s foreign policy, to the extent that he has one, tends toward isolationism, while Bolton’s is expansive but heavily unilateral, spurning allies when necessary. At times, though, unilateralism can sound a lot like America First. Both Bolton and Trump are dismissive of the international architecture of treaties and alliances, which was largely constructed by the United States following the Second World War. At the 2018 G-20 summit, in Buenos Aires, a gathering of the world’s largest economies, Bolton instigated a confrontation over the communiqué that announced the meeting’s results. As the document was being drafted, according to an American official who was present, one of Bolton’s aides began taking out phrases—“gender equality,” “multilateral institutions,” “rules-based international order.” The official told me, “He would point to a phrase and say, ‘This won’t pass the Bolton test.’ ” Bolton’s unilateralist approach permeates the N.S.C. “ ‘The post-World War Two rules-based global order’?” a Bolton staffer said to me. “What does that mean?”

Most national-security advisers work behind the scenes. Bolton has been unusually visible, travelling to Moscow to meet the Russian foreign minister, Sergey Lavrov; to Jerusalem to meet Netanyahu; and to Ankara to meet the Turkish President, Recep Tayyip Erdoğan. On Twitter, he has admonished the Russians for attempting to project influence in Latin America, and expressed gratitude to Ivanka Trump for “supporting women’s economic empowerment” in Africa. The Western diplomat told me that Bolton differed from other White House advisers, such as Secretary of State Mike Pompeo, who reflexively agree with the President. “Pompeo is really interested not in foreign policy but in what is good for Trump. When you are out of the Trump field, he has nothing to say,” the diplomat told me. “When you meet Bolton, it’s a real conversation on any issue, no matter how obscure.”

The former senior national-security official told me, “Trump feels aligned with Bolton. He talks tough—he’s a hawk. Trump likes that.” Still, it’s not clear how much influence Bolton—or any senior adviser—has over the President.

In April, 2018, during Bolton’s first week in office, Bashar al-Assad’s regime in Syria dropped chemical weapons—probably chlorine gas—into a densely populated suburb of Damascus. The gas caused agonizing deaths for at least forty-nine people and sickened at least six hundred and fifty others, many of them women and children. The previous year, Trump had responded to a similar attack by ordering a strike, in which fifty-nine missiles were fired at a government airbase. This time, when Bolton asked the Pentagon for options, Mattis gave only one, a limited strike with cruise missiles. Bolton was furious, a person familiar with his thinking told me: “Mattis is an obstructionist. He seemed to forget that it was the President who was elected.” After some modifications, Trump authorized the attack. But Bolton wanted more; he believed that the U.S. needed a more enduring military presence in Syria.

.. When McMaster was the national-security adviser, he had carefully limited the scope of the mission in Syria, maintaining a deployment of some two thousand troops, dispatched by Obama in 2014. Their orders were to kill isis fighters and to train local soldiers, but not to fight Assad’s government, his Iranian and Russian backers, or their proxies in Hezbollah, the Lebanese armed group and political party. An adviser on Middle East issues told me that senior officials at the Pentagon and in national security had regarded the deployment as highly successful. “We were trying to follow the President’s guidance that this force was there to destroy isis, and that’s it,” the adviser said.

Last summer, at a meeting with officials involved in Syria, Bolton announced that the mission was being expanded. According to the adviser on Middle East issues, who attended the meeting, Bolton told the group, “I don’t care about Syria, but I do care about Iran.” He said that the American forces would stay in Syria until the Iranians left—potentially for years. Bolton told his aides to communicate the new policy to the Russians, and he declared it publicly in September, 2018.

Trump had been suggesting for months that the mission in Syria was nearly concluded. “We were very successful against isis,” he told a group of Eastern European leaders that April. “We’ll be successful against anybody militarily. But sometimes it’s time to come back home.” Now he was saddled with an open-ended military commitment, of a kind that he had repeatedly vowed to avoid. Bolton told me that he had secured the President’s permission to expand the mission, but the adviser on Middle East issues disagreed: “What’s obvious is that Bolton does not speak for the President.”

In December, Erdoğan, the Turkish leader, offered Trump a way out. During a phone call with the President, he said that his troops could take over the job of securing Syria, leaving American forces free to go home. Turkey had its own interest in this arrangement: a large swath of territory near the Syrian border is controlled by ethnic Kurds, whom the Turks consider mortal enemies. The U.S. considers the Kurds allies, but Trump nevertheless leaped at the offer. “Erdoğan told the President that he could kill the terrorists in northeastern Syria, and the President said, ‘Fine, O.K., you do it,’ ” the source familiar with Bolton’s thinking told me.

The White House announced the withdrawal of American forces shortly after Trump hung up, sending a wave of concern through the Middle East. These troops, even with a limited mission, had served as a counterweight to the various armed groups that are active in Syria—Turks, Russians, the remaining isis loyalists, Assad’s soldiers. They also helped give the U.S. leverage in determining whether Assad’s regime remained in power after the war. “I think they are drinking champagne in Damascus,” the former senior Administration official told me.

To Bolton and others, it was clear that Turkey took the announcement as a green light to send troops into northeastern Syria. “For Erdoğan, that meant killing our Kurdish allies there,” the source familiar with Bolton’s thinking said. He suggested that Erdoğan and Trump had simply misunderstood each other: “They were two ships passing in the night.” After conversations with aides, Trump reconsidered, the source said: “The President has spoken to Erdoğan several times since then, and he has made clear to him, ‘Don’t come across, don’t kill Kurds.’ ”

Trump has recently expressed willingness to leave a small American force in Syria, but its exact size has not been settled; officials say that it may be as few as two hundred troops. “They are making it up as they go along,” a Senate staffer who works on national-security issues told me. When I first spoke to Bolton about the reduction in forces, he seemed disappointed. “Sometimes you win, sometimes you lose,” he said. A few weeks later, though, he was more cheerful as he outlined an ambitious roster of operations that appeared to mirror the one the President had tried to scale back: restraining the Iranians, limiting the Russians’ territory, keeping the Turks away from the Kurds. The adviser on Middle East issues suggested that Bolton was responsible for the entire affair, because he’d tried to push the President too far. “It’s a catastrophe, and I blame Bolton,” he said.

In July, 2017, after Kim Jong Un test-fired a new missile, Trump posted an arch tweet: “Does this guy have anything better to do with his life?” But, that summer, there was evidence that the White House was concerned. As the regime launched a series of ballistic-missile tests, Trump ordered the Pentagon to begin removing the spouses and children of military personnel from South Korea. (“Mattis just ignored it,” the Administration official told me.) Since then, Trump has alternated between belligerent tweets and attempts to find a diplomatic solution. At the summit in Hanoi, he was seeking “the big deal”—the denuclearization of the country at one stroke.

Shortly before joining the White House, Bolton described a grimly constrained set of options, which seemed to preclude diplomacy. “You’re getting down fairly quickly to a binary choice: live with a North Korea with nuclear weapons, or look at military force,” he said. “These are not attractive options, but that’s where we’re headed.”

In fact, Bolton has believed for decades that these are the only two choices. In the early two-thousands, as the Bush Administration was negotiating to limit North Korea’s nuclear program, Bolton stridently advocated war. Wilkerson, Powell’s chief of staff, was so concerned that he brought Bolton into a private meeting on the consequences of military strikes: “I gave him a ten-minute brief on what a war with North Korea would look like—a hundred thousand casualties in the first thirty days, many of them Americans. The Japanese that would die. The Chinese that would die. The fact that Seoul, one of the most modern and forward-looking cities in the world, would probably be reduced to the Dark Ages. I told him, ‘That’s Passchendaele, John. That’s Ypres.’ ”

He said that Bolton was unmoved: “John looked at me and said, ‘Are you done? Clearly, you do war. I don’t do war. I do policy.’ ”

Bolton’s skepticism about negotiating with North Korea has largely been confirmed; several successive Administrations have failed to talk the regime into giving up its nuclear program. Now that the problem has fallen to the Trump Administration, though, Bolton is in the same position as the officials he’s been deriding for twenty-five years. The failure of the talks in Hanoi means that the North Korean regime can work toward a nuclear weapon capable of hitting the United States. “They haven’t demonstrated that capacity yet,” the Administration official said. But even a medium-range weapon would pose a threat to much of Asia.

The Administration official, like others, was reluctant to speak about what might happen if North Korea does not back down. A strike to destroy the country’s nuclear capability would have catastrophic effects throughout the region. Even if the United States could cripple North Korea’s nuclear facilities, it could not eliminate its conventional weapons quickly enough to prevent them from being used. These include thousands of artillery pieces and mortars near the border with South Korea. Seoul, which has a population of ten million, including some two hundred thousand Americans, could suffer tens of thousands of casualties. In 2017, Mattis told reporters that a conflict on the Korean Peninsula would be “probably the worst kind of fighting in most people’s lifetimes.”

Even in the White House, there seems to be a growing realization that military force is not a realistic option. “I think we could have destroyed the North’s nuclear program in the nineteen-nineties—it was more concentrated, and we knew where everything was,” the Administration official told me. “Not anymore. It’s too big and too dispersed.”

But Bolton still believes that such a strike is possible, the source familiar with his thinking said: “We can still do it. We know where most, if not all, of their weapons are—we could destroy their nuclear capability. There are ways to deal with their artillery.” When I asked about potential casualties, he said that Bolton “wishes we weren’t at this point. But the military option remains viable.”

The primary negotiating tool that remains is economic sanctions. The senior Administration official told me that the fiscal pressure on North Korea is greater than ever. Kim, the official said, has repeatedly told the North Korean people that their years of suffering and hardship will finally end. “We think that he has raised expectations, and now he has to follow through,” he said.

Not long after the summit, Kim complained in a speech that the American team had come to Hanoi with “completely unrealizable plans.” Unless Trump changed his thinking, Kim said, “the U.S. will not be able to move us one iota even if they sat with us a hundred, a thousand times.” He added, however, that he was open to a third summit—extending an eighteen-month sequence of insults and meetings, during which the North Korean regime has continued to refine its weapons. In response, Trump described his relationship with Kim as “excellent.” In April, North Korea test-fired another missile.

Bolton was nonplussed by Kim’s test. “That was their way of giving us the little finger,” the source familiar with his thinking said. “Not the big finger—just a little one.” The big finger came a week later: Kim held a summit with Vladimir Putin to discuss the nuclear situation. Afterward, Putin called for a return to “international law, instead of the rule of the fist.”

People who have worked with Bolton say that he is focussed less on North Korea than on Iran, where his vigilance can sometimes seem out of proportion to the apparent threat. “There are only two countries that can really threaten the United States—China and Russia,” the former senior national-security official said. “But Bolton has had this anal focus on Iran for twenty years. I don’t know why.” When I asked Bolton about it, he said, “I care about Iran because I care about nuclear weapons.”

On February 11th, Bolton released a video on Twitter, in which he addressed Ayatollah Ali Khamenei, the Supreme Leader of Iran. In a professorial tone, he noted that it was the fortieth anniversary of the Iranian Revolution and enumerated what he saw as its results: repression at home, terrorism abroad, a dismal economy, and the enmity of the world. “So, Ayatollah,” he said, “for all your boasts, for all your threats to the life of the American President, you are responsible for terrorizing your own people and terrorizing the world as a whole. I don’t think you’ll have many more anniversaries to enjoy.”

The Trump Administration has persistently spoken out against Iran, but it has also made scattershot efforts at diplomacy. A senior Iranian official told me that, in 2017, Trump sent eight requests to meet with the Iranian President, Hassan Rouhani. “Trump invited President Rouhani to dinner!” the official told me. Rouhani evidently declined, but, a few weeks before Bolton posted his video on Twitter, there was another apparent attempt. Admiral Ali Shamkhani, the secretary of Iran’s national-security council, told an Iranian news agency that a U.S. official had approached him, during a visit to Afghanistan, and “asked to hold talks.” Shamkhani didn’t say whether Iran had responded, but a Middle Eastern businessman told me that, around the same time, an Iranian official had asked him to pass a message to the White House.

Mattis served as a brake on confrontation. In late 2017, Iraq was preparing for parliamentary elections, and McMaster grew concerned about Iran’s efforts to influence the outcome. He asked the Pentagon to provide options to counter the Iranian campaign. As the elections approached, one of McMaster’s aides told me, a Pentagon official came to the White House. “I asked him what happened to the options,” the former aide said. “He told me, ‘We resisted those.’ You could feel everyone in the meeting go, ‘Excuse me?’ ”

During the Obama Administration, the sanctions on Iran were designed to force the regime to agree to limit its nuclear program. Under Trump, the goal is apparently to make the Iranian people so miserable that they will overthrow the government. “After all the experience we’ve had with regime change, I think we’re out of that business,” a senior member of Trump’s foreign-policy team told me. “We can collapse their economy—it’s not that difficult. But it’s up to the Iranian people.”

Bolton suggested that the policy was working. “The opposition to the regime has widened,” he said. “There have been riots. You don’t always read about this in the Western press, because they don’t let reporters see it.” Although the United States has withdrawn from the nuclear accord, the Iranian regime continues to adhere to it. Funding to Hezbollah, Iran’s primary foreign proxy, has been cut substantially. Nervousness about the future has frozen foreign investment. With inflation at nearly fifty per cent, and with one in four young Iranians out of work, the economy is under extreme stress. Iranian oil exports, which rose to 2.8 million barrels a day after sanctions were lifted, have been severely diminished, at times to less than a million barrels a day. It’s possible that the Iranian government will be ousted. But allies worry that the White House is squeezing the regime so hard that it might force a confrontation, perhaps a military one. “They’re not giving the Iranians any room,” the Western diplomat told me. “It’s implosion or surrender.”

Sadjadpour, the Iran expert, believes that the tensions inside the White House over Iran have not been resolved. “Trump doesn’t want to go to war—he doesn’t want to intervene anywhere,” he told me. Trump’s real goal, he suggested, was the pageantry of public negotiations. The main obstacle to direct talks is Khamenei, he said; having the United States as an enemy has been a linchpin of the regime’s self-justification. “Bolton’s worst nightmare is that Khamenei will write Trump a letter saying, ‘Why don’t we get together and talk?’ Because he knows that Trump would jump at that opportunity.”

In April, Bolton travelled to Coral Gables, Florida, to speak to the surviving members of Brigade 2506, a group of Cuban exiles who fought in the American-backed invasion at the Bay of Pigs. It was the fifty-eighth anniversary of the operation, which ended in catastrophe; the annual commemoration has become a kind of Miami Passion play.

As the aging veterans gathered for lunch, at the Biltmore Hotel, large screens played a documentary about the operation, with black-and-white footage of combat and interviews with survivors, many of whom still feel that they were betrayed by irresolute allies in the United States. “The invasion failed precisely because of President Kennedy’s order not to provide air support and to destroy the Cuban Air Force,” one veteran says.

As Bolton came to the lectern, the veterans, some of them in wheelchairs, gave him a hero’s welcome. Bolton announced new economic sanctions on the Cuban government and assailed Obama for attempting a rapprochement, which Trump has rolled back. “The Trump Administration will never, ever abandon you!” Bolton declared. “We will always have your back.”

As the crowd applauded, Bolton broadened his speech to attack other leftist governments—especially in Venezuela, where the regime of Nicolás Maduro is trying to ride out an economic collapse and a nationwide uprising. Bolton has led the White House’s charge against Maduro, accusing him of forming, along with Cuba and Nicaragua, a “troika of tyranny” in the Western Hemisphere. They aid one another, Bolton said, pointing to the Cuban security forces inside Venezuela, and all of them were aided by Obama. “In no uncertain terms, the Obama Administration’s policies toward Cuba have enabled the Cuban colonization of Venezuela,” he said.

For a national-security adviser, this was remarkably close to a campaign speech—a radical departure from the habits of Bolton’s predecessors. It was also a departure from Bolton’s habits; he resists being called a neocon, but in Venezuela he was trying to oust a regime that poses no immediate threat. When I asked him about it, in his office soon after the speech, he argued that Venezuela was dangerous, because it was allowing Russia to gain a foothold in the region. He said that there were twenty thousand Cubans in Venezuela who served as “surrogates for the Russians.” There were also at least a hundred Russian soldiers and mercenaries on the ground, helping Maduro stay in power. “To get the Russians out, you have to change the regime,” he said.

As the crowd applauded, Bolton broadened his speech to attack other leftist governments—especially in Venezuela, where the regime of Nicolás Maduro is trying to ride out an economic collapse and a nationwide uprising. Bolton has led the White House’s charge against Maduro, accusing him of forming, along with Cuba and Nicaragua, a “troika of tyranny” in the Western Hemisphere. They aid one another, Bolton said, pointing to the Cuban security forces inside Venezuela, and all of them were aided by Obama. “In no uncertain terms, the Obama Administration’s policies toward Cuba have enabled the Cuban colonization of Venezuela,” he said.

For a national-security adviser, this was remarkably close to a campaign speech—a radical departure from the habits of Bolton’s predecessors. It was also a departure from Bolton’s habits; he resists being called a neocon, but in Venezuela he was trying to oust a regime that poses no immediate threat. When I asked him about it, in his office soon after the speech, he argued that Venezuela was dangerous, because it was allowing Russia to gain a foothold in the region. He said that there were twenty thousand Cubans in Venezuela who served as “surrogates for the Russians.” There were also at least a hundred Russian soldiers and mercenaries on the ground, helping Maduro stay in power. “To get the Russians out, you have to change the regime,” he said.

The source familiar with Bolton’s thinking pointed out another incentive: Venezuela has the largest proven oil reserves in the world. “Who is in control of the oil fields—the United States or Russia?” he asked. “The President said he would have taken the oil in Iraq. Well, look at how much oil Venezuela has.”

With Trump’s national-security team depleted—no permanent Secretary of Defense, no Secretary of Homeland Security, no Ambassador to the United Nations—Bolton would have extraordinary latitude in a crisis. “John understands that you have to get the elected leader the approval of the audience that matters,” Hundt said. “As long as Trump’s base is still applauding, then Bolton can do whatever he wants.”

For Bolton, it is ultimately a question of sovereignty. “The Monroe Doctrine is alive and well,” he said. “It’s our hemisphere.” The doctrine, he noted, was a prohibition against outside powers interceding in Latin America. “That doesn’t mean armed force,” he said. “That’s the Roosevelt Corollary. I haven’t invoked that—yet.” But, he argued, as he has innumerable times in the past thirty years, “all options are on the table.” ♦

A Mar-a-Lago Weekend and an Act of God: Trump’s History With Deutsche Bank

At Deutsche Bank, Mr. Offit’s mandate was to lend money to big real estate developers, package the loans into securities and sell the resulting bonds to investors. He said in an interview that one way to stand out in a crowded market was to make loans that his rivals considered too risky.

In 1998, a broker contacted him to see if he would consider lending to a Wall Street pariah: Mr. Trump, who was then a casino magnate whose bankruptcies had cost banks hundreds of millions of dollars.

Mr. Offit took the meeting.

A few days later, Mr. Offit’s secretary called him. “Donald Trump is in the conference room,” she whispered. Mr. Offit said he rushed in, expecting to find an entourage. Mr. Trump was alone.

He was looking for a $125 million loan to pay for gut renovations of 40 Wall Street, his Art Deco tower in Lower Manhattan. Mr. Offit was impressed by the pitch, and the loan sailed through Deutsche Bank’s approval process.

Mr. Trump seemed giddy with gratitude, Mr. Offit recalled. He took Mr. Offit golfing. He flew him by helicopter to Atlantic City for boxing matches. He wrote a grateful note to Sidney Offit for having “a great son!”

Mr. Offit commissioned a detailed model of 40 Wall Street. A golden plaque on its pedestal bore the names and logos of Deutsche Bank and the Trump Organization. Mr. Offit gave one to Mr. Trump and kept another in his office.

Mr. Trump soon came looking for $300 million for the construction of a skyscraper across from the United Nations headquarters. The loan was approved. He wanted hundreds of millions more for his Trump Marina casino in Atlantic City. Mr. Offit pledged to line up cash for that, too.

Not long after, Edson Mitchell, a top bank executive, discovered that the signature of the credit officer who had approved the Trump Marina deal had been forged, Mr. Offit said. (Mr. Offit was never accused of forgery; the loan never went through.)

Mr. Offit was fired months later. He said it was because Mr. Mitchell claimed that he was reckless, a charge Mr. Offit disputed.

It was the first hiccup in the Trump relationship. It would not be the last.

Over the next few years, the commercial real estate group, with Mr. Kennedy now in a senior role, kept lending to Mr. Trump, including to buy the General Motors building in Manhattan. Occasionally, Justice Kennedy stopped by Deutsche Bank’s offices to say hello to the team, executives recalled.

At an annual pro-am golf tournament the bank hosted outside Boston in the early 2000s, Mr. Trump sat down for a recorded interview with the bank’s public relations staff, who asked about his experience with Deutsche Bank.

“It’s great,” Mr. Trump exclaimed, according to a person who witnessed the interview. “They’re really fast!”

In 2003, a Deutsche Bank team led by Richard Byrne — a former casino-industry analyst who had known Mr. Trump since the 1980s — was hired to sell bonds on behalf of Trump Hotels & Casino Resorts. Bank officials escorted Mr. Trump to meet institutional investors in New York and Boston, according to an executive who attended.

The so-called roadshow seemed to go well. At every stop, Mr. Trump was greeted by large audiences of fund managers, executives and lower-level employees eager to see the famous mogul. The problem, as a Deutsche Bank executive would explain to Mr. Trump, was that few of them were willing to entrust money to him.

Mr. Trump requested an audience with the bank’s bond salesmen.

According to a Deutsche Bank executive who heard the remarks, Mr. Trump gave a pep talk. “Fellas, I know this isn’t the easiest thing you’ve had to sell,” the executive recalled Mr. Trump saying. “But if you get this done, you’ll all be my guests at Mar-a-Lago,” his private club in Palm Beach, Fla.

The sales team managed to sell hundreds of millions of dollars worth of bonds. Mr. Trump was pleased with the results when a Deutsche Bank executive called, according to a person who heard the conversation.

“Don’t forget what you promised our guys,” the executive reminded him.

Mr. Trump said he did not remember and that he doubted the salesmen actually expected to be taken to Mar-a-Lago.

“That’s all they’ve talked about the past week,” the executive replied.

Mr. Trump ultimately flew about 15 salesmen to Florida on his Boeing 727. They spent a weekend golfing with Mr. Trump, two participants said.

A year later, in 2004, Trump Hotels & Casino Resorts defaulted on the bonds. Deutsche Bank’s clients suffered steep losses. This arm of the investment-banking division stopped doing business with Mr. Trump.

.. Mr. Trump told Deutsche Bank his net worth was about $3 billion, but when bank employees reviewed his finances, they concluded he was worth about $788 million, according to documents produced during a lawsuit Mr. Trump brought against the former New York Times journalist Timothy O’Brien. And a senior investment-banking executive said in an interview that he and others cautioned that Mr. Trump should be avoided because he had worked with people in the construction industry connected to organized crime.

Nonetheless, Deutsche Bank agreed in 2005 to lend Mr. Trump more than $500 million for the project. He personally guaranteed $40 million of it, meaning the bank could come after his personal assets if he defaulted.

By 2008, the riverside skyscraper, one of the tallest in America, was mostly built. But with the economy sagging, Mr. Trump struggled to sell hundreds of condominium units. The bulk of the loan was due that November.

Then the financial crisis hit, and Mr. Trump’s lawyers sensed an opportunity.

A provision in the loan let Mr. Trump partially off the hook in the event of a “force majeure,” essentially an act of God, like a natural disaster. The former Federal Reserve chairman Alan Greenspan had called the financial crisis a tsunami. And what was a tsunami if not a natural disaster?

.. One of Mr. Trump’s lawyers, Steven Schlesinger, told him the provision could be used against Deutsche Bank.

“It’s brilliant!” Mr. Schlesinger recalled Mr. Trump responding.

Days before the loan was due, Mr. Trump sued Deutsche Bank, citing the force majeure language and seeking $3 billion in damages. Deutsche Bank countersued and demanded payment of the $40 million that Mr. Trump had personally guaranteed.

With the suits in court, senior investment-banking executives severed ties with Mr. Trump.

.. Ms. Vrablic’s superiors encouraged her to make loans that rival banks dismissed as too large or complex. They saw it as a way to elbow into the hypercompetitive New York market.

.. One of Ms. Vrablic’s clients was Jared Kushner, who married Ivanka Trump in 2009. Mr. Kushner regarded Ms. Vrablic as the best banker he had ever worked with, according to a person familiar with his thinking.

Shortly after the Chicago lawsuit was settled, Mr. Kushner was told that Mr. Trump was looking for a loan and introduced him to Ms. Vrablic, according to people familiar with the relationship.

.. Mr. Trump flew Ms. Vrablic to Miami to show her a property he wanted to buy: the Doral Golf Resort and Spa. He needed more than $100 million for the 72-hole property.

Deutsche Bank dispatched a team to Trump Tower to inspect Mr. Trump’s personal and corporate financial records. The bankers determined he was overvaluing some of his real estate assets by as much as 70 percent, according to two former executives.

.. By then, though, Mr. Trump had become a reality-TV star, and he was swimming in cash from “The Apprentice.” Deutsche Bank officials also were impressed that Mr. Trump did not have much debt, according to people who reviewed his finances. Aside from his history of defaults, he was an attractive borrower.

Mr. Trump also expressed interest in another loan from the private-banking division: $48 million for the same Chicago property that had provoked the two-year court fight.

Mr. Trump told the bank he would use that loan to repay what he still owed the investment-banking division, the two former executives said. Even by Wall Street standards, borrowing money from one part of a bank to pay off a loan from another was an extraordinary act of financial chutzpah.

.. Investment-banking executives, including Anshu Jain, who would soon become Deutsche Bank’s co-chief executive, pushed back. Lending to Mr. Trump again would be foolish, they argued, and signal to clients that they could default and even sue the bank.

Executives in the private bank countered that the proposed loans had Mr. Trump’s personal guarantee and therefore were low risk. And the Chicago loan, they noted, would lead to the repayment of tens of millions of dollars that Mr. Trump still owed the investment-banking division.

A top executive with responsibility for the private bank discussed the loans with Mr. Ackermann, the chief executive, who supported them, according to two officials. A powerful committee in Frankfurt, which evaluated loans based on risks to the bank’s reputation, signed off.

“There is no objection from the bank to proceed with this client,” wrote Stuart Clarke, the chief operating officer for the Americas, in a Dec. 5, 2011, email, according to a recipient.

Deutsche Bank wired the money to Mr. Trump. The loans carried relatively low interest rates, executives said, but the business promised to be profitable: As part of the deal, Mr. Trump would hold millions of dollars in a personal account, generating fees for the bank.

“I have no recollection of having been asked to approve that private-banking loan,” Mr. Ackermann said in an interview. He added: “I would have approved it, if it came to me, if it was commercially sound.”

Ms. Vrablic’s relationship with the Trumps deepened.

Deutsche Bank lent money to Donald Trump Jr. for a South Carolina manufacturing venture that would soon go bankrupt. It provided a $15 million credit line to Mr. Kushner and his mother, according to financial documents reviewed by The Times. The bank previously had an informal ban on business with the Kushners because Jared’s father, Charles, was a felon.

In 2012, Jared Kushner recommended that the editor of The Mortgage Observer, one of the publications he owned, write a profile of Ms. Vrablic. The editor, Carl Gaines, knew Mr. Kushner was her client and objected, according to a person familiar with the exchange.

“Just go meet with her,” Mr. Kushner said. “You’ll figure something out.”

gauzy profile of Ms. Vrablic was published in February 2013.

Shortly afterward, the private bank produced a promotional video featuring some of its marquee clients. The video was played at a retreat for Deutsche Bank’s senior leadership in Barcelona. In it, Ivanka Trump extolled the private bank’s work with her family and thanked their relationship manager, according to two people who saw the video.

.. In early 2014, Mr. Trump and his personal lawyer, Michael Cohen, approached Ms. Vrablic about more potential loans.

The owner of the Buffalo Bills had died, and the N.F.L. franchise was up for sale. Mr. Trump was interested, and he needed to show the league he had the financial wherewithal to pull off a transaction that could top $1 billion.

Mr. Trump asked Ms. Vrablic if the bank would be willing to make a loan and handed over bare-bones financial statements that estimated his net worth at $8.7 billion.

.. Mr. Cohen testified to Congress last month that the documents exaggerated Mr. Trump’s wealth. Deutsche Bank executives had reached a similar conclusion. They nonetheless agreed to vouch for Mr. Trump’s bid, according to an executive involved.

Mr. Trump’s bid did not win, but another lending opportunity soon arose.

A federal agency had selected Mr. Trump to transform the Old Post Office Building in Washington into a luxury hotel. But his financial partner — the private equity firm Colony Capital, run by Thomas J. Barrack Jr. — pulled out. Mr. Trump needed nearly $200 million.

.. Because of his decades-long pattern of defaults and his increasingly polarizing political rhetoric — among other things, he had been spreading a lie about President Barack Obama being born overseas — Mr. Trump remained untouchable for most banks.

Ms. Vrablic was willing to help.

In a memo outlining the rationale for the Old Post Office loan, Ms. Vrablic said Mr. Trump was expected to add large sums to his brokerage account if he received the loan, according to an executive who read the document.

This time, there was less internal opposition. One reason: Mr. Jain — by then the bank’s co-chief executive — had a solid relationship with Ms. Vrablic. Mr. Jain accompanied her to meetings with high-profile clients, and he praised her work to colleagues, multiple executives said.

..On a foggy Wednesday in February 2013, Ms. Vrablic and Mr. Jain went to Trump Tower to meet with Mr. Trump, according to two executives with knowledge of the meeting. Ms. Vrablic’s rapport with the client was immediately clear: Mr. Trump’s assistant greeted her as an old friend, and she seemed relaxed with Mr. Trump and his daughter, one executive said.

.. They discussed Mr. Trump’s finances over lunch, and Mr. Jain said he was surprised by his low level of debt, the executives said. After lunch, Ms. Vrablic told her colleagues that Mr. Jain had sounded upbeat about Mr. Trump’s finances.

A $170 million loan to pay for the overhaul of the Old Post Office went through in 2015, and Mr. Trump added more money to his brokerage account. (In May 2016, he reported up to $46 million of stocks and bonds in the account.)

.. On Aug. 6, 2015, Mr. Trump participated in the first Republican presidential debate. He clashed with the Fox News moderator, Megyn Kelly. He flew back to New York early the next morning. That evening, he called in to a CNN talk show and said of Ms. Kelly that there was “blood coming out of her wherever.”

In the intervening hours, Mr. Trump had used a black Sharpie to sign documents for another loan from Deutsche Bank: $19 million for the Doral resort. That brought to more than $300 million the total lent under Ms. Vrablic.

.. On the campaign trail, rivals assailed Mr. Trump’s financial history. In response, he pointed to Deutsche Bank-funded successes like the Old Post Office project, now a gleaming hotel a few blocks from the White House.

.. In early 2016, Mr. Trump asked Ms. Vrablic for one final loan, for his golf course in Turnberry, Scotland.

.. Ms. Vrablic said yes, but a fight soon erupted.

Jacques Brand, who was in charge of Deutsche Bank’s American businesses, angrily objected, partly because of Mr. Trump’s divisive rhetoric.

Ms. Vrablic appealed the decision. Senior executives in Frankfurt, including Christian Sewing, who would become chief executive in 2018, were shocked that the private bank would consider lending Mr. Trump money during the campaign, bank officials said.

The bank’s reputational risk committee killed the transaction in March 2016.

.. That same month, as The Times was preparing an article about Mr. Trump’s excommunication from Wall Street, he cited his warm relationship with Deutsche Bank.

.. “They are totally happy with me,” he said to The Times. “Why don’t you call the head of Deutsche Bank? Her name is Rosemary Vrablic. She is the boss.”

.. After Mr. Trump won the election, Deutsche Bank’s board of directors rushed to understand how the bank had become the biggest lender to the president-elect.

A report prepared by the board’s integrity committee concluded that executives in the private-banking division were so determined to win business from big-name clients that they had ignored Mr. Trump’s reputation for demagogy and defaults, according to a person who read the report.

The review also found that Deutsche Bank had produced a number of “exposure reports” that flagged the growing business with Mr. Trump, but that they had not been adequately reviewed by senior executives.

.. On Deutsche Bank’s trading floor, managers began warning employees not to use the word “Trump” in communications with people outside the bank. Salesmen who violated the edict were scolded by compliance officers who said the bank feared stoking public interest in its ties to the new president.

One reason: If Mr. Trump were to default on his loans, Deutsche Bank would have to choose between seizing his assets or cutting him a lucrative breaka situation the bank would rather resolve in private.

.. Two years after Mr. Trump was sworn in, Democrats took control of the House of Representatives. The chamber’s financial services and intelligence committees opened investigations into Deutsche Bank’s relationship with Mr. Trump. Those inquiries, as well as the New York attorney general’s investigation, come at a perilous time for Deutsche Bank, which is negotiating to merge with another large German lender.

Next month, Deutsche Bank is likely to start handing over extensive internal documents and communications about Mr. Trump to the congressional committees, according to people briefed on the process.

Ms. Vrablic, who is intensely private and rarely discusses her personal life with colleagues, declined to comment. People familiar with her thinking said she expected to be called to testify publicly on Capitol Hill.

Donald Trump’s Phony America

There are several kinds of success stories. We emphasize the ones starring brilliant inventors and earnest toilers. We celebrate sweat and stamina. We downplay the schemers, the short cuts and the subterfuge. But for every ambitious person who has the goods and is prepared to pay his or her dues, there’s another who doesn’t and is content to play the con. In the Trump era and the Trump orbit, these ambassadors of a darker side of the American dream have come to the fore.

.. What a con Holmes played with Theranos. For those unfamiliar with the tale, which the journalist John Carreyrou told brilliantly in “Bad Blood,” she dropped out of Stanford at 19 to pursue her Silicon Valley dream, intent on becoming a billionaire and on claiming the same perch in our culture and popular imagination that Steve Jobs did. She modeled her work habits and management style after his. She dressed as he did, in black turtlenecks. She honed a phony voice, deeper than her real one.

She spoke, with immaculate assurance, of a day when it might be on everyone’s bathroom counter: a time saver, a money saver and quite possibly a lifesaver. She sent early, imperfect versions of it to Walgreens pharmacies, which used it and thus doled out erroneous diagnoses to patients. She blocked peer reviews of it and buried evidence of its failures.

This went on not for months but for years, as Holmes attracted more than $900 million of investment money and lured a breathtakingly distinguished board of directors including two former secretaries of state, George Shultz and Henry Kissinger; a former secretary of defense, William Perry; and a future secretary of defense, James Mattis. What they had before them wasn’t proof or even the sturdy promise of revolutionary technology. It was a self-appointed wunderkind who struck a persuasive pose and talked an amazing game.

She was eventually found out, and faces criminal charges that could put her in prison. But there’s no guarantee of that. Meantime she lives in luxury. God bless America.

Theranos was perhaps an outlier in the scope of its deceptions, but not in the deceptions themselves. In an article titled “The Ugly Unethical Underside of Silicon Valley” in Fortune magazine in December 2016, Erin Griffith tallied a list of aborted ventures with more shimmer and swagger than substance, asserting: “As the list of start-up scandals grows, it’s time to ask whether entrepreneurs are taking ‘fake it till you make it’ too far.”