To understand the President’s path to the 2020 election, look at what he has provided the country’s executive class.
Prescott Bush, the father and grandfather of future Presidents, was the eight-time club champion on the golf course at the Round Hill Club, one of eight country clubs in Greenwich, Connecticut. Bush was a staunch believer in standards; he required his sons to wear a jacket and tie for dinner at home. He was tall, restrained, and prone to righteousness; friends called him a “Ten Commandments man.” In the locker room at Round Hill, someone once told an off-color joke in front of his fourteen-year-old son, George H. W. Bush, and Prescott stormed out, saying, “I don’t ever want to hear that kind of language in here again.”
In Greenwich, which had an unusually high number of powerful citizens, even by the standards of New York suburbs, Prescott Bush cast a large shadow; he was an investment banker, the moderator of the town council, and, from 1952 to 1963, a United States senator. In Washington, he was President Eisenhower’s golf partner, and the embodiment of what Ike called “modern Republicanism.” Prescott wanted government lean and efficient, but, like Nelson Rockefeller, the New York governor whose centrism inspired the label Rockefeller Republican, he was more liberal than his party on civil rights, birth control, and welfare. He denounced his fellow-Republican Joseph McCarthy for creating “dangerous divisions among the American people” and for demanding that Congress follow him “blindly, not daring to express any doubts or disagreements.” Bush could be ludicrously aristocratic—he had his grandchildren call him Senator—but he believed, fundamentally, in the duty of government to help people who did not enjoy his considerable advantages. He supported increasing the federal minimum wage and immigration quotas, and he beseeched fellow-senators, for the sake of science, education, and defense, to “have the courage to raise the required revenues by approving whatever levels of taxation may be necessary.”
Long after Bush died, in 1972, his family stayed central to the community of Greenwich Republicans. His son Prescott, Jr., known as Pressy, served as the chairman of the Republican Town Committee; alumni of the Bush Administrations still live around town. Each year, the highest honor bestowed by the Connecticut Republican Party is the Prescott Bush Award.
When Donald Trump ran for President, he was hardly a natural heir to the Greenwich Republican tradition. In the eighties, he bought a mansion on the town’s waterfront, but he did not often observe the prim Yankee ethic inscribed on the Greenwich coat of arms: fortitudine et frugalitate—courage and thrift. Locals were embarrassed by the house’s gilded décor, and, after he and his wife Ivana divorced, she sold it. When George H. W. Bush called for a “kinder, gentler nation,” Trump responded, “If this country gets any kinder or gentler, it’s literally going to cease to exist.” In early 2016, even before Trump was asserting his right to “locker-room talk,” he was denounced in Greenwich Time, the town’s daily newspaper, by Leora Levy, a prominent local fund-raiser. “He is vulgar, ill-mannered and disparages those whom he cannot intimidate,” she wrote. Levy—the latest winner of the Prescott Bush Award—was lending her support to Prescott’s grandson Jeb Bush, the former governor of Florida.
But not everyone in Greenwich was excited about Jeb. Jim Campbell was the chairman of the Republican Town Committee. The Campbells, like the Bushes, had deep roots in town. Jim prepped at Exeter and graduated from Harvard and Harvard Law School, before working in Europe and returning home as a real-estate executive. On a fall evening, Campbell attended a reception for Jeb Bush at the Belle Haven Club, a private tennis-and-boating club overlooking Long Island Sound. Jeb was expansive and mild, which struck Campbell as precisely wrong for the political moment: “He gave a whole talk about a woman named Juanita in South Florida, and how ‘immigration is love,’ and I just looked at the people I came with and said, ‘Does he think he’s already the nominee? He’s running in a tough Republican primary, and just because we’re at the Belle Haven Club doesn’t mean we’re all voting for him.’ ”
At home one night, watching television, Campbell happened on a Trump rally in Iowa. “I’m not a hard-core conservative—I’m a Republican from Greenwich,” Campbell said. “But I listened, and he had that line that he would use: ‘Folks, we either have a country or we don’t.’ And I felt the chill—like Chris Matthews with the little Obama zing up the leg. I’m, like, ‘Oh, my God, this is a really good line.’ ” To Campbell, Trump was describing immigration in ways that resonated: “Could somebody finally say that we’re allowed to enforce the law at the border without being called a racist? I lived in Switzerland for ten years. Do you think I was allowed to go around without a passport?”
Campbell tapped out a text message to a friend: “Trump live – can’t turn the channel. Unbelievable. I don’t think any R can beat him.” Campbell watched the rally for forty-five minutes. “He was mesmerizing,” he said. Not long afterward, he saw a Republican debate in which Trump described the invasion of Iraq as a mistake. For Campbell, the acknowledgment came as a catharsis. “Of course it was a big, fat mistake,” he told himself. “He says everything I think.”
In early 2016, Campbell attended a dinner for Republicans at the Delamar Greenwich Harbor, a Mediterranean-themed boutique hotel that is popular with local finance executives. After a dinner speaker mocked the notion of building a wall and imposing tariffs, Campbell raised his hand: “I said, ‘With all due respect, why is it that we’re not allowed to support a candidate who supports the things that you just ticked off?’ ” Campbell knew that his question would cause a stir, but he had decided that it was time “to let everybody know who I was supporting.” When the event was over, he discovered that he was not alone: “I had four guys make a beeline for me, Wall Streeters, all saying, ‘What can we do? Can I sign up? Are you organizing?’ ”
In February, 2016, with Jeb still vying for the nomination, Campbell endorsed Trump. “I just think there’s a lot of people supporting Donald and don’t want to say so,” he told a local reporter. That spring, as Connecticut Republicans prepared to vote in their primary, political observers predicted that John Kasich, the moderate governor of Ohio, would prevail in towns and cities from Greenwich to Fairfield—a stretch of American bounty known as the Gold Coast. Instead, Trump largely dominated the region.
Four years later, Trump signs are still scarce in Greenwich (population 62,600), but his supporters are easy to find. There is the first selectman—the local equivalent of mayor—and the chairman of the Greenwich finance board, as well as an ardent backer who serves in the state House of Representatives. Some local Republicans helped fund Trump’s Inauguration, and some joined his White House, including Linda McMahon, the former professional-wrestling executive who headed the Small Business Administration, and Hope Hicks, Trump’s longtime communications adviser. (She once captained the Greenwich high-school lacrosse team.) Others in town have abandoned their objections to Trump. Leora Levy, who called him vulgar in the local paper, took to applauding his “leadership” and quoting him on Twitter, where she adopted some of his rhetorical style. “america will never be a socialist country!!!” she posted. “we are born free and will stay free!!!” Last fall, Trump nominated her to be the American Ambassador to Chile.
How did America’s country-club Republicans, the cultural descendants of Prescott Bush, learn to love Donald Trump? They don’t have much in common with the clichéd image of his admirers: anxious about losing status to minorities, resentful of imperious élites, and marooned in places where life expectancy has fallen. But the full picture has never been that simple. As early as May, 2016, exit polls and other data showed that Trump supporters earned an average of seventy-two thousand dollars a year, while supporters of Hillary Clinton earned eleven thousand dollars less. Two-thirds of Trump’s supporters had incomes higher than the national median—sometimes, as in Greenwich, much higher.
I grew up in Greenwich, on Round Hill Road, not far from the club where Prescott Bush stormed out of the locker room. My great-grandparents Albert and Linda Sherer moved to town from Chicago in 1937. Albert was a Republican who worked in advertising for the National Biscuit Company, and Linda raised their two children. They were renters until 1968, when they bought a white Colonial with a wide lawn. The house passed down through the generations, and, when I was nine years old, my parents moved the family from Brooklyn to Greenwich, into a world of uncountable advantages. In 1994, I graduated from Greenwich High School, which is the rare public school that has a championship water-polo team and an electron microscope. (It was a donation, obtained by an award-winning science teacher.)
People around town have never much cared for caricatures of the place—the starchy patricians, the chinless wonders, the history of exclusion—even when there is truth in them. For decades, many African-Americans and Jews were prevented from buying homes. In 1975, protesters came to town with signs reading “cocktail bigots” and “share the summer,” because Greenwich barred nonresidents from a public beach—a restriction that lasted until the state Supreme Court overturned it, in 2001. Nobody pretends that bigotry has vanished, but these days the town has more diversity than outsiders expect. Thirty-eight per cent of its public-school students are minorities, mostly Latino; in some elementary schools, at least half the students qualify for free or reduced-price lunch. Many of their parents work in local service jobs, bearing high rents and expenses in order to access some of the country’s best public schools. Frank Farricker, a real-estate developer and a Democratic activist, said, “I tell everybody that Greenwich only discriminates on the basis of one color: green.”
The seacoast of Fairfield County has always been one of America’s most affluent places, but in recent decades it has sprinted ahead of the rest of the country. In 2016, according to federal estimates, it was the wealthiest metropolitan area in the United States, outstripping the oil country of Midland, Texas, and the technology hub of San Francisco. Even though a string of tycoons have fled Connecticut in search of lower taxes, the latest Forbes ranking of the world’s billionaires lists fifteen of them in the “Greater Greenwich Area,” led by Ray Dalio, the founder of the hedge fund Bridgewater, who is worth an estimated eighteen billion dollars.
From afar, it is easy to misread the politics of the place: like much of America’s coasts, the Gold Coast has swung left, culturally and politically, since the days of Prescott Bush. The largest share of voters in Greenwich today are unaffiliated; Republicans still hold an edge over Democrats, but the margin is less than four thousand registered voters. In 2016, nobody was surprised that Clinton beat Trump in Greenwich, fifty-seven per cent to thirty-nine. But that portrait—of liberal cosmopolitans appalled by Trump—obscures a potent element of American politics: the executive class of the Republican Party. Its members are wealthier, more conservative, and more politically active than their forebears, in ways that have helped Trump reach the White House, survive impeachment, and fortify his bid for reëlection during the anguish of the coronavirus pandemic. Understanding how he retains the overwhelming support of Republicans requires an accounting of not only what he promised Americans at the bottom but also what he provides Americans at the top.
The story of Trump’s rise is often told as a hostile takeover. In truth, it is something closer to a joint venture, in which members of America’s élite accepted the terms of Trumpism as the price of power. Long before anyone imagined that Trump might become President, a generation of unwitting patrons paved the way for him. From Greenwich and places like it, they launched a set of financial, philanthropic, and political projects that have changed American ideas about government, taxes, and the legitimacy of the liberal state.
The former congressman Christopher Shays is a moderate Republican who was elected eleven times to represent the Gold Coast, from 1987 to 2009. Now conservatives mock him as a rino—a Republican in name only. “When Sean Hannity calls someone like me a rino, I want to punch him in the nose,” Shays told me. “I got elected as a Republican for thirty-four effing years, and Hannity has never gotten elected for anything.” When Shays talks to former staff and constituents in Connecticut, he has come to recognize the delicate language of accommodation: “I was talking to a guy I know well, after some pathetic thing that Trump did, and his response was ‘Yes, but he’s selecting the right Supreme Court Justices.’ I started to laugh at him, because I know for a fact that’s a minor issue for him.” Shays believes that many Americans quietly share Trump’s desire to reduce immigration and cut social-welfare programs for the poor. “He’s saying what people think, and they appreciate that,” Shays said. “But not many are going to admit that’s why they support him.”
When it comes to the essential question—will Trump get reëlected?—the answer rests heavily on a persistent mystery: how many Americans plan to vote for him but wouldn’t say so to a pollster? In Greenwich, Edward Dadakis, a corporate insurance broker who has been involved with Republican politics for fifty years, told me that many of his friends are “below the radar screen.” He went on, “In a sense, I’m one of them. I’m out there in the public domain, so people know where I stand, but in 2016, for the first election ever, I did not put a bumper sticker on my car.” He worries how strangers will react. He said, “I still have two ‘Make America Great Again’ hats at home, wrapped in plastic.”
The southern panhandle of Connecticut is cradled between the gray-blue waters of Long Island Sound and the wooded border of New York State. In politics and in culture, it’s a mashup of New England and New York, a place settled by Puritans who agonized over what the historian Missy Wolfe calls “the proper balance between their flock’s economic success and the level of success that they deemed would offend God.” Long after the Puritans were gone, the tension remained in a seesawing battle between the Brahmin and the buccaneer, service and profit, restraint and greed. For much of the twentieth century, the Brahmin had the advantage.
In 1927, Owen D. Young, a Greenwich resident who was the first chairman of General Electric, gave a speech at Harvard Business School, in which he scolded businessmen who “devise ways and means to squeeze out of labor its last ounce of effort and last penny of compensation.” He encouraged them instead to “think in terms of human beings—one group of human beings who put their capital in, and another group who put their lives and labor in a common enterprise for mutual advantage.” Rick Wartzman, a longtime head of the Drucker Institute and a historian of corporate behavior, told me, “This really was beyond rhetoric. We were much more of a ‘we’ culture than an ‘I’ culture.” On Young’s watch, G.E. became one of the first American companies to give workers a pension, profit-sharing, life insurance, medical coverage, loans, and housing assistance.
One of America’s most powerful capitalists, Reginald Jones, who became G.E.’s chairman and C.E.O. in 1972, lived in a modest brick Colonial in Greenwich. His daughter, Grace Vineyard, told me, “He asked my mom, ‘Do you want anything more?’ And she said, ‘Why would we want anything more?’ ” Leo Hindery worked for Jones as a junior executive. “I earned fifteen thousand six hundred dollars when I got out of Stanford, and Reg’s salary was two hundred thousand dollars,” Hindery said. “G.E. was the preëminent company in America, and the C.E.O. was making twelve or thirteen times what I did.” According to the Economic Policy Institute, that ratio wasn’t unusual: in 1965, the C.E.O. of an average large public company earned about twenty times as much as a front-line worker. Today, that figure is two hundred and seventy-eight times.
The moderate consensus was always shakier than it looked, and by the mid-sixties it was gyrating out of control. In 1955, William F. Buckley, Jr., had established his magazine National Review on the principle that government exists only “to protect its citizens’ lives, liberty and property. All other activities of government tend to diminish freedom and hamper progress.” It was the opening shot of the modern conservative movement, though, on the whole, liberal intellectuals did not regard it as a serious challenge. In 1963, John Kenneth Galbraith, the liberal economist and adviser to the Kennedys, mocked the modern conservative for being engaged in “one of man’s oldest, best financed, most applauded, and, on the whole, least successful exercises in moral philosophy. That is, the search for a truly superior moral justification for selfishness.”
In Greenwich, however, some people were seized by the new conservatism. J. William Middendorf II was a Harvard-educated investment banker who had served on the town council with Prescott Bush, his friend and neighbor. “I sold him a piece of land at the foot of my property,” Middendorf told me. When he retired to his porch in the evening, he could hear the Bushes singing Yale songs in their back yard. But, beneath the similarities, Middendorf had adopted a strikingly different ideology; he had become, in his words, a “disciple” of the libertarian movement, enthralled by Friedrich Hayek and Joseph Schumpeter. He condemned Eisenhower’s moderates for regarding government as “a working tool that should be used to shape society.” Instead, he wrote, “I believe that society is shaped by individuals.”
Middendorf wanted to push libertarianism into mainstream politics, and he found a vehicle in Barry Goldwater, the fiery Arizona senator. Goldwater, the heir to a department-store fortune in Phoenix, ran for President in 1964, fuelled by what he described as “my resentment against the New Deal.” Goldwater’s campaign was a backlash against liberalism—the antiwar movement, civil rights, welfare—but also against moderate Republicans. Nelson Rockefeller was a “cardboard candidate,” Middendorf told me. “He could speak for an hour, but I honestly could not remember a single word he ever said.” Middendorf became Goldwater’s campaign treasurer, raising money from other well-to-do dissidents of the East Coast establishment. “He was obviously out of the mainstream, and we had an uphill battle,” he said.
They prevailed that summer, at the Republican National Convention, in San Francisco. Rockefeller made a desperate last attempt for relevance: from the lectern, he denounced the advent of a “radical” right-wing element within the Party, in the hope that the moderates would rise up and resist. Instead, the hall erupted in boos. Jackie Robinson, the black baseball star and an avatar of integration among Republicans, heard the catcalls and felt, as he said later, like “a Jew in Hitler’s Germany.” Middendorf, who was also in attendance, received Rockefeller’s denunciation as an affirmation. “He was talking about me and my friends,” he wrote, in “Potomac Fever,” his political memoir.
In the general election, Goldwater lost—spectacularly—to Lyndon Johnson. But his brand of libertarian, antitax absolutism found a fervent audience among American executives who were confronting an alarming change: after a quarter century of relentless growth, American profits were declining. Japan and Western Europe, finally rebuilt after the Second World War, were formidable new competitors; the Arab oil shock of 1973 triggered the longest recession since the thirties. Moreover, the environmental and consumer-protection movements had hastened new regulations, on products ranging from flammable fabrics to cigarettes and bank loans.
Executives felt besieged. “They decided regulation was mostly to blame,” the historian Rick Perlstein writes in his forthcoming book, “Reaganland.” In Perlstein’s telling, “the denizens of America’s better boardrooms, who had once comported themselves with such ideological gentility, began behaving like the legendary Jacobins of the French Revolution. They declared war without compromise.” Back home in Greenwich, Middendorf—who went on to work in the Nixon, Ford, and Reagan Administrations—gloried in having vanquished the moderates. He wrote, “We created the conditions that put conservative Republicans back in power after more than thirty years of domination by the liberal eastern establishment—the so-called ‘Country Club’ Republicans.”
Ashort drive from the Round Hill Club, in a Georgian manor overlooking a lake, lived Lee and Allie Hanley, who were early converts to the conservative movement. Lee had graduated from St. Paul’s and from Yale, where he played polo, squash, and soccer, and he had taken over Hanley Co., his family’s brick-and-oil business. He was a bon vivant, with a fondness for salmon-colored slacks, and a ready checkbook for political ventures. “Very warm and engaging,” a Greenwich friend said. “A collector of curiosities, a Renaissance man at sort of a superficial level. More of a gut player who wanted to be in the game.” Allie was a devout Christian with a keen interest in politics. The 1980 Republican primary was shaping up to be a contest between the old Republican Party and the new—George H. W. Bush, a Washington insider known around town as Poppy, versus Ronald Reagan, the conservative governor of California. On that question, the Hanleys broke with their neighbors in Greenwich. “For us, it was never Bush country,” Allie told me recently. “It was always Reagan country.”
Roger Stone, who was Reagan’s campaign director for the Northeastern states, recalled that most people in Greenwich recoiled from his candidate: “They thought, Reagan, oh, my God, he’s another Goldwater. He has no chance in the general election. He’s a cowboy-movie actor.” (Stone, who later became a Trump confidant, spoke to me last year, before he was convicted of lying to Congress during Robert Mueller’s investigation.) “Hanley was the only high Wasp we had,” Stone continued. “All the ‘right’ people were for Poppy.”
The Hanleys, hoping to spread their enthusiasm in Greenwich, agreed to host a reception at their home. But, when they met Reagan to discuss the plans, over lunch at the Pierre Hotel, Allie saw a problem. “He had on a brown tie, and it was ghastly,” she told me. “When you go to a different part of the country, the most important thing you need to do is dress like they do. They feel more comfortable talking to you. So I ran to Bloomingdale’s, and I bought four ties.” When the Reagans turned up for the party, Allie said, “Here’s a gift for you! Go upstairs and freshen up.” Reagan came back down a few minutes later, and the offending tie had been replaced by her gift. “He wore it on all the posters after that,” she said.
Stone and Lee Hanley adopted an approach that uncannily prefigured Trump’s electoral strategy: they built a coalition of conservative élites and the white working class. Hanley introduced Stone to small-business owners in Greenwich, many of them Italian-American—“mining for Catholic votes,” as Stone called it. “Lee was very well connected with the merchants in town—the grocer, the butcher,” Stone said. “He could talk to anybody. He was not stuffy like some Wasps.” Hanley told Stone before one visit, “We’re going to have to drink some espresso, but we can get them.” The strategy worked; in the Connecticut primary, Reagan beat Bush in the Bush-family stronghold of the southern panhandle. In 1984, Reagan rewarded Hanley by nominating him to the board of the Corporation for Public Broadcasting. Two years later, he became the chairman.
In the next three decades, Hanley and other wealthy conservatives—Richard Scaife, John Olin, the Koch brothers—helped train a generation of Republicans in Congress to adhere to ideological orthodoxy. Hanley made a string of historic political investments. He saved Regnery, America’s most prominent conservative book publisher, with a crucial infusion of cash. He helped found the Yankee Institute for Public Policy, the Connecticut affiliate of a network of think tanks that advocate for low taxes and small government. He became the principal backer of a political consulting firm formed by Stone and two other young Reaganites, Charlie Black and Paul Manafort. “We had the credentials and the potential business and all that, but we didn’t have any money,” Black told me. “Lee was a good friend, so we approached him.” Black, Manafort & Stone, as they called themselves, became pioneering lobbyists, known for their brazen use of what Manafort described as “influence peddling.” Clients included Rupert Murdoch’s News Corp. and a young real-estate developer named Donald Trump.
By the end of the century, the courtly politics of Prescott Bush were gone, a change accelerated by the decisions of his son George H. W. Bush. George had inherited his father’s restraint—at school in Greenwich, he was nicknamed Have-Half, for his willingness to share—and also the family tradition of public service. But, running for President in 1988, Bush unleashed his brawling campaign manager Lee Atwater on the governor of Massachusetts, Michael Dukakis. Atwater vowed to “strip the bark off the little bastard.” In the most searing moment, a political-action committee linked to the Bush campaign paid for a television ad blaming Dukakis for the case of Willie Horton, a convict who had committed rape during a furlough from a Massachusetts prison. The ad crudely exploited white fears, showing pictures of Horton, who was African-American, while a narrator spoke of kidnapping, rape, and murder. Atwater denied any involvement in the ad, but Bush recognized the power of the rhetoric, and took to mentioning Horton almost daily on the stump. Atwater boasted that he would make Horton “Dukakis’s running mate.”
Not long before Atwater died, in 1991, he apologized to Dukakis for the “naked cruelty” of that campaign. But the Willie Horton strategy was the forerunner of a more savage era in American politics—of Swift Boat attacks on a war hero; of the racist birther fiction against America’s first black President—and it pushed candidates to avoid looking weak by advancing tough-on-crime policies that both parties now view as devastating for low-income and minority Americans.
In the end, Bush was “a gentleman, but he was a politician, too,” his biographer Jon Meacham wrote. For all Bush’s decency, he had decided early on that, in order to serve, he needed to win. In a tape-recorded diary entry near the end of the 1988 campaign, Bush told himself, “The country gets over these things fast. I have no apologies, no regrets, and if I had let the press keep defining me as a wimp, a loser, I wouldn’t be where I am today.”
In the early years of this century, the economic divisions that would come to define America in the age of Trump became evident on the lush back roads of Greenwich, in a sign so subtle that it was easy to miss. Many of the new estates going up were no longer surrounded by the simple stone walls, stacked to the height of a farmer’s hip, that crossed the New England landscape. Instead, the builders introduced a more imposing barrier: tall, stately walls of chiselled stone, mortared in place.
The fashion for higher walls had little to do with safety; Greenwich has one of the lowest crime rates in America. To Frank Farricker, who served on the town’s planning-and-zoning commission, they symbolized power and seclusion. “Instead of building two or three feet high, people got into six-footers—the ‘Fuck you’ walls,” he said. When nearby municipalities noticed the trend, they treated it like an invasive species; they rewrote zoning rules to prevent the spread of what stonemasons took to calling “Greenwich walls.”
The walls were products of one of the most extraordinary accumulations of wealth in American history. In much of the country, the corporate convulsions of the seventies had entailed layoffs, offshoring, and declining union power, but on Wall Street they inspired a surge of creativity. Since the seventeen-hundreds, Wall Street had focussed mostly on funnelling American savings into new businesses and mortgages. But, in the last two decades of the twentieth century, financiers and economists opened vast new realms of speculation and financial engineering—aggressive methods to bet on securities, merge businesses, and cut expenses using bankruptcy laws. U.S. stock markets grew twelvefold, and most of the gains accrued to the wealthiest Americans. By 2017, Wall Streeters were taking home twenty-three per cent of the country’s corporate profits—and home, for many of them, was Connecticut.
The Internet allowed financiers to work from anywhere, so some escaped New York’s higher taxes by relocating their offices closer to where they lived. Newspapers took to calling Greenwich the “Hedge Fund Capital of the World.” The dealmakers earned vastly more than the industrial executives they had replaced. In 2004, Institutional Investor reported that the top twenty-five hedge-fund managers earned an average of two hundred and seven million dollars a year.
Nine of those top managers lived or worked in Greenwich, led by Edward Lampert, who in 2004 earned an estimated $1.02 billion after orchestrating the merger of Kmart and Sears. Lampert was not one to dress like a gardener; just offshore, he docked his yacht, a two-hundred-and-eighty-eight-foot vessel that he had named Fountainhead, for Ayn Rand’s individualist fable. (Trump has said that he identifies with the book’s hero, Howard Roark, a designer of skyscrapers who declares, “I do not recognize anyone’s right to one minute of my life. . . . No matter who makes the claim, how large their number, or how great their need.”) So much individual wealth accumulated in southern Connecticut that tax officials took to monitoring the quarterly payments of a half-dozen of the richest taxpayers, because their personal earnings would affect how much the entire state was able to spend on public services.
The money physically redrew Greenwich, as financiers built estates on a scale once favored by Gilded Age railroad barons. The hedge-fund manager Steven A. Cohen paid $14.8 million in cash for a house, then added an ice rink, an indoor basketball court, putting greens, a fairway, and a massage room, ultimately swelling the building to thirty-six thousand square feet—larger than the Taj Mahal. In a final flourish, Cohen obtained special permission to surround his estate with a wall that exceeded the town’s limits on height. It was nine feet tall.
When the tide began to turn against Wall Street, you could follow it from my family’s front door. Up and down Round Hill Road, neighbors became known for one imbroglio after another. If you took a right turn out of our driveway, you could wander by the stone Colonial house of Walter Noel, a money manager with a gracious Nashville accent, who funnelled billions of his clients’ dollars to the grifter Bernie Madoff. (Noel claimed that he, too, was duped.) If you turned left, you reached the estate of the hedge-fund manager Raj Rajaratnam, who once celebrated his birthday by flying in Kenny Rogers to sing “The Gambler” over and over, until Rogers finally refused. In 2009, Rajaratnam was arrested as part of a stock-cheating case that the F.B.I. called Operation Perfect Hedge. He was given a sentence of eleven years in prison, the longest ever for insider trading. Eventually, so many neighbors were ensnared in financial scandals that a local blogger nicknamed our street Rogues Hill Road.
In truth, nobody was shocked that the vast new fortunes of the Gold Coast contained the seeds of financial catastrophe. In the run-up to the 2008 crisis, William Wechsler was a managing director at Greenwich Associates, a consulting firm, where he saw financiers taking ever-larger risks. Historically, the bylaws of the New York Stock Exchange had required trading firms, such as Goldman Sachs, to be private partnerships. “When it was time for you to go, you sold your share to the next generation,” Wechsler told me. “It was culturally acceptable to get to a certain level of success and retire happy.” But, by 1999, the rules had changed, the big banks had become public companies, and investors expected large returns. Hedge funds and other firms made huge bets, in pursuit of dramatic windfalls. Instead of directing most of their capital to funding businesses that hired people and made things, the financiers in New York and Connecticut had become an economy unto themselves. “Every year that goes by, more and more of the added value in our society goes toward capital, and less and less toward labor,” Wechsler told me. “What you end up with is a very unstable society.”
On top of that, Wall Street was hiring lobbyists to dismantle regulations that protected the country from an economic fiasco. In some cases, Greenwich residents led the big banks that lobbied for destructive changes. John Reed was a co-chairman of Citigroup, and William B. Harrison, Jr., was the chief executive of JPMorgan Chase. Their banks were two of the largest contributors to Senator Phil Gramm, the Texas Republican who engineered a ban on the regulation of over-the-counter derivatives. Later, the government’s official autopsy of the collapse called that ban “a key turning point in the march toward the financial crisis,” because “derivatives rapidly spiraled out of control and out of sight.”
As the economy quaked, the shock waves reverberated through politics. The Tea Party movement raged against Obama, taxes, and social-welfare programs, helping Republicans to greater gains in the 2010 midterms than in any congressional election in six decades. Even in Greenwich, where people are not quick to hoist placards, Tea Party activists protested in front of Town Hall, and the first selectman Peter Tesei, the town’s top elected official, joined in. “Liberty has contracted today because the role of government has expanded,” he told the crowd. (Tesei, like many of his ideological allies, later pledged to support Trump.)
The sentiment was a familiar one—even the Romans resented their taxes—but Grenwich was not traditionally known for absolutism on the subject. In the nineteen-eighties, Leowell Weicker, a Greenwich Republican who had served as first selectman and gone on to the U.S. Senate, became known in Washington for blocking Reagan’s attempts to cut spending on health and education. In 1991, after Weicker became governor, he imposed Connecticut’s personal income tax, which was so unpopular that protesters cursed and spat at him. In a speech that fall, he said, “Respect—if not reëlection—comes from speaking the truth.”
But, to some in the current generation, especially Greenwich’s new concentration of libertarians, a fiercer resistance to taxes and to government was a matter of moral principle. Cliff Asness, a billionaire who runs AQR Capital Management, was among the most vocal. When Governor Andrew Cuomo, of New York, discussed raising taxes on hedge funds, Asness tweeted that he was a “flat out lying demagogue,” who was trying to run a “gulag not a state.” Around town, the expectation that a person of substantial means might pay substantial taxes no longer held sway. That became especially clear in 2013, when Thomas Foley, a Greenwich private-equity investor, ran for governor. He owned a yacht, a number of vintage cars, two British fighter jets, and a house that Greenwich Time likened to “the Hogwarts castle.” But, on tax returns that he showed reporters, he had claimed so many investment losses and alimony payments that his federal taxes amounted to six hundred and seventy-three dollars that year. (Foley lost the race.)
Charles Rossotti, a Republican businessman who served as the commissioner of the I.R.S. from 1997 to 2002, has estimated that sophisticated tax ploys and shelters cause ordinary citizens to pay an extra fifteen per cent in taxes each year. Brooke Harrington, an economic sociologist at Dartmouth, told me, “Some of that shortfall just never gets made up. Those are roads that don’t get improved, public transport that doesn’t get built, schools that don’t get fixed.” Connecticut has the richest one per cent of any state, but, according to several studies of crumbling infrastructure, its roads are among the worst in the country.
Harrington said, “For an earlier generation, even if your heart wasn’t in it, you’d say, ‘I’ve got to join the local charity board, to project that I deserve this wealth.’ ” The current generation, instead of focussing on the local charity board, prefers targeted private philanthropy, bypassing public decisions on whom to help and how. “The underlying massive change is that wealth no longer needs to justify itself—it is self-justifying,” Harrington said. “I look back, and I think, That’s when we gave up on being a ‘we.’ ”
In the political ferment brought on by the Tea Party and the resistance to Obama, conservative donors expanded their influence. The Hanleys became funders of Turning Point USA, a nonprofit, founded in 2012, that promotes conservatism in high schools and colleges. More important, Allie Hanley helped its founder, Charlie Kirk, meet other donors. “Allie Hanley opened the entire southern corridor for us,” he wrote later. Kirk is now a conservative celebrity and the chairman of Students for Trump, a campus political network. In recent years, Turning Point has faced multiple controversies. Some student governments have sought to ban it for interfering in their elections; staff and members have been discovered making racist comments. Last year, a video showed Riley Grisar, the head of a Turning Point chapter in Nevada, saying “white power,” with his arm wrapped around a woman who said, “Fuck the niggers.” (Grisar was removed from the organization.)
Lee Hanley used his fortune to elevate candidates on the right wing of the Republican Party. In 2014, he donated some three hundred and fifty-seven thousand dollars; the money went to stars such as Ted Cruz, but also to oddball outsiders like Chris McDaniel, a Mississippi state lawmaker and former talk-radio host who was trying to unseat the incumbent senator, Thad Cochran. McDaniel lost, but his campaign themes were a preview of politics to come; before Trump was popularizing anti-immigrant rhetoric, McDaniel was pledging to block increases in residency permits and work visas. (When McDaniel ran for the Senate again, in 2018, he embraced a blunter racial message, arguing to preserve a Confederate emblem on the state flag.)
But none of Hanley’s political investments would pay off as well as an obscure project for which Steve Bannon, Trump’s former strategist, calls him one of the nation’s “unsung heroes.” Not long after Mitt Romney lost to Obama, in 2012, Hanley commissioned a pollster named Patrick Caddell to investigate why conventional Republican candidates were underperforming. Caddell had made his name advising Jimmy Carter, but he had broken with Democrats and begun appearing frequently on Fox News. As he and Hanley discussed the project, both suspected that the electoral returns suggested a deep frustration with the status quo. “I said, ‘I think something’s happening in the country,’ ” Caddell recalled. “Lee said, ‘You know, I think something may be, too. I want you to go out and just find out.’ ” Caddell’s polls quickly suggested that the “level of discontent in this country was beyond anything measurable.”
In 2013, Hanley asked Caddell to show his findings to Bannon, and to another patron, the hedge-fund billionaire Robert Mercer. They huddled over the data during a conservative conference in Palm Beach. The numbers, Caddell told them, indicated a public appetite for a populist challenger who could run as an outsider, exposing corruption and rapacity. He called it the Candidate Smith project—the search for a political savior along the lines of “Mr. Smith Goes to Washington.”
When Trump took an early lead in 2015, most of the political and financial world ignored him. Jeffrey Sonnenfeld, a professor at the Yale School of Management, attended a salon that summer at the Connecticut home of Larry Kudlow, the business commentator who now leads Trump’s National Economic Council. “It was a lot of very deep-pocketed Republicans from Greenwich and New York,” Sonnenfeld told me. “Not one person had a pleasant thing to say about Trump.” Sonnenfeld urged them to take Trump’s chances seriously, but a fellow-guest, who worked for a super pac supporting Ted Cruz in the primaries, disagreed. “She said, ‘I’m a lifelong expert on the psychographics of women’s voter behavior, and I can tell you that Donald Trump will never get two per cent of Republican women voters,’ ” Sonnenfeld told me. “She got wild applause. That was Kellyanne Conway.” (Conway, now a senior adviser to Trump, called this a “specious, self-serving claim,” adding, “I don’t know ‘Professor’ So-and-So.”)
But Caddell and Hanley concluded that Trump was the closest thing they would find to a Candidate Smith. He had none of Reagan’s optimism, but he had name recognition, money, and a preternatural sense of how a billionaire could surf the rage kicked up by the financial crisis. Their conviction persuaded Mercer to invest in Trump, and other wealthy donors followed. As Election Day approached, Charlie Glazer, a Greenwich money manager who had served as George W. Bush’s Ambassador to El Salvador, began talking to friends, “rationalizing why we should all vote for Trump,” one recalls.
For some, it was a plainly calculated choice. Thomas Peterffy, a billionaire who owned the largest estate in Greenwich, donated to Trump but never pretended to admire him. “When the choice is between two ideologies, then it’s a luxury to dwell on the personalities of the candidates,” he told me. “It’s a luxury that we cannot afford.” Peterffy, who made his fortune as a pioneer in digital trading, said that the choice was between “a high degree of government regulation or a diminished amount of government regulation, because, basically, that’s how the U.S. will get to socialism—increasing government regulation.”
When the votes were counted, Trump’s greatest support in Greenwich was not in the middle-class sections of downtown. It was in two of the wealthiest precincts—the Tenth and Eleventh Districts, which sprawl across the lush northern backcountry, encompassing the Round Hill Club, where Prescott Bush once reigned, and the estate of Steven Cohen, the investor with the nine-foot wall. Cohen, whose hedge fund closed in 2014, after pleading guilty to insider trading, donated a million dollars to support the Inauguration. Peterffy chipped in a hundred and fifty thousand dollars. Glazer joined the transition.
Hanley didn’t live to see it. He died in Greenwich, four days before the 2016 election. Bannon wishes that more people knew about his discreet contribution to the movement. “Lee Hanley is like, when you read the history of the American Revolution or the Civil War—all these great events—you find out about these individuals in back that never won any credit, but, if it was not for them, the victory would not be achieved,” he told a conservative audience in 2017. “He had a real love of the hobbits, of the deplorables, and he put his money where his mouth was.”
Every town in America has its story of what changed after the 2016 election. In Greenwich, the Trump era started almost instantly. In December, a town employee reported to police that Christopher von Keyserling, a well-known member of the town council, had touched her groin after saying, “I love this new world. I no longer have to be politically correct.” Lynn Mason, the accuser, warned him not to touch her again, to which he allegedly replied, “It would be your word against mine, and nobody will believe you.” After the town government contacted von Keyserling about the complaint, he said that Mason had overreacted to a “little pinch,” according to court records. He was charged with misdemeanor sexual assault. He pleaded not guilty and is awaiting trial.
The combination of Trump and the von Keyserling incident caused an immediate reaction in Greenwich: women signed up to run for office, and more than fifty won seats on the town council. “A lot of us just woke up,” Joanna Swomley, a retired lawyer who entered the race, said. “We were horrified.” Swomley organized a local chapter of Indivisible, a progressive network, to heighten public engagement. It worked. In 2017, Greenwich Democrats won control of the town finance board for the first time in recorded history; the next year, they won seats in the state legislature that no Democrat had occupied since Herbert Hoover was in the White House.
But the blue wave quickly subsided. In 2019, Republicans reclaimed control of the finance board, and elected as first selectman a local businessman and state lawmaker named Fred Camillo, who had voted for Trump. At the voting booths, Swomley sensed a change in the atmosphere. “I was holding a Democrat’s sign, and a Republican yelled out, ‘Oh, hell no!’ It was not the embarrassment, the quietness that you saw in 2017. It was ‘I am going to own this. I like this.’ ”
Claire Tisne Haft, a Greenwich Time columnist who lives in town with her husband and three kids, was appalled by Trump, and she assumed that her neighbors were, too. She got her first indication to the contrary at a dance recital for her daughter, when another mother told her how excited she was to “see what Trump can do.” Not long afterward, Tisne Haft and her husband had dinner with friends, and the conversation turned to politics. “We realized halfway through the meal that we had to adjust our tone,” she told me.
In March, 2019, a seemingly unrelated bit of news helped illuminate Trump’s local support. That month, a powerful Greenwich attorney named Gordon Caplan, the co-chairman of the law firm Willkie Farr & Gallagher, was indicted for paying seventy-five thousand dollars for a test proctor to fix his daughter’s ACT exam. Caplan was one of fifty-three defendants in the college-admissions scandal, a list dotted with addresses in Greenwich, Atherton, and Bel Air. In phone calls recorded by the F.B.I., Rick Singer, the consultant behind the scam, had explained to Caplan that his daughter would never know that her family had cheated on her behalf: “She will think that she’s really super smart and she got lucky on a test.” Caplan uttered one of the scandal’s indelible expressions: “To be honest, I’m not worried about the moral issue here.” Caplan pleaded guilty and served a month in prison.
In a column after the scandal broke, Tisne Haft wrote that the case brought up “a whole lot of uncomfortable in a town like Greenwich.” It exposed how far some of America’s most powerful, educated, and prosperous people will go to give their families an advantage in a life already full of them.
Tisne Haft sensed that some people in town had become so cynical about the workings of power that they had lost their moral footing. “A friend said, ‘You know those kids whose parents gave libraries to their colleges? How is that so different than pushing the boundaries of the truth about your kid?’ ” Tisne Haft told me. “I just had to look at this person and say, ‘Hang on. Someone Photoshopped a kid’s head onto a picture.’ I feel like we jumped off a cliff there somewhere and didn’t notice.”
The admissions case reminded me of the rationale I kept hearing for looking past Trump’s behavior toward women, minorities, immigrants, war heroes, the F.B.I., democracy, and the truth, not to mention his request that Ukraine “do us a favor” by investigating his political opponents: a conviction that, ultimately, nothing matters more than cutting taxes and regulations and slowing immigration. Places like Greenwich take pride in their commitment to civility and decency, but Caplan’s indifference to the “moral issue,” as he put it, bespoke the kind of quiet compromises that a person makes in the privacy of a phone call, or a voting booth.
Even before the 2020 campaign was under way—before the rise and fall of Elizabeth Warren and Bernie Sanders, before the virus that upturned every assumption about the race—it was clear that the essential fault line in American politics was inequality. At times, this anger showed up on the Gold Coast. In 2017, activists staged a bus tour of Greenwich, called “Lifestyles of the Rich and Shameless,” which stopped outside the homes (or, more often, the walls) of local financiers. They left giant “tax bills,” charging the owners for what the tour’s organizers called “the havoc they’ve wreaked on our economy.” At the time, Connecticut was considering cutting four thousand state jobs, to relieve a $1.7-billion budget deficit. The activists’ final stop was at the office of the libertarian Cliff Asness, where they erected a giant inflatable pig, chomping on a cigar.
As of last year, America’s four hundred richest individuals owned about three trillion dollars in wealth—more than all black households and a quarter of all Latino households combined, according to the Institute for Policy Studies. In calmer moments, Americans have tended to regard our largest fortunes as a kind of national spectacle and, for some, a source of inspiration. Now polls routinely confirm a survey by NBC News and the Wall Street Journal, in which seventy per cent of Americans describe themselves as angry “because our political system seems to only be working for the insiders with money and power.”
Amid this populist outrage, some prominent citizens of Greenwich have joined the ranks of business leaders who say that capitalism must change in order to survive. Dalio, the town’s richest resident, calls income inequality a “national emergency”; his family philanthropy has donated to Connecticut public schools. Last fall, the hedge-fund manager Paul Tudor Jones urged a Greenwich audience to recognize that workers have been shortchanged, though he hastened to reassure attendees: “It wasn’t because good people did bad things. It was unfortunately just a natural, unchecked movement.” Alan Barry, the town’s commissioner of human services, told me that he applauds the concern but disagrees with the notion that inequality was unforeseeable. “Stated policies combined to create this,” he said. “Now you’re turning around and saying, ‘Whoa, we’ve got runaway capitalism.’ ”
The targets of broad American antipathy tend not to look inward for its source. “It’s all this rapid technological change that results in income inequality,” Peterffy told me. “It suddenly increases productivity, and we need fewer workers to produce the same amount of goods and services.” One remedy, he said, is direct payments to citizens, and he has become an advocate for replacing all government benefits with a universal basic income: “It is much, much cheaper to give the people money and not restrict business in any way.” I asked Peterffy, who built a fortune worth an estimated fourteen billion dollars, if he thought America could have avoided radical inequality by not permitting people like him to amass so much money. “Well, it would have decreased my incentive to work as hard as I did,” he said. “The number of times I nearly went bankrupt, if I would have had an easier way out, I probably would’ve chosen that.” In 2017, Peterffy sold his Greenwich estate; he now lives in Florida, which has no state income tax.
If you are among the Greenwich élite, whether you love Trump or hate him, it is easy to count the ways that he has oriented his Administration to help people like you. When Trump introduced his tax bill, he called it a gift to “the folks who work in the mail rooms and the machine shops of America.” That was absurd. The bill cut the corporate tax rate by fourteen per cent, and most of the windfall went to investors in the form of dividends and stock buybacks. Trump pledged to “eliminate tax breaks and complex loopholes” favored by the rich. Though he limited the deductions for state and local taxes, wealthy citizens were compensated by new tax breaks, including some specifically for the commercial-real-estate industry and for wealthy heirs. On average, Trump gave households in the top one per cent a forty-eight-thousand-dollar tax cut, while those in the bottom twenty per cent received a hundred and twenty dollars, according to the Institute on Taxation and Economic Policy, a nonpartisan think tank. Jim Campbell, the Republican organizer who embraced Trump early in 2016, told me recently, “I don’t know anyone who voted for Donald Trump in 2016 and won’t vote for him again. In Greenwich, he’ll probably pick up some votes.”
This spring, when the pandemic paralyzed New York City, the effects echoed through the suburbs; the city of Stamford reported that a crematory had caught fire after wiring melted from overuse. As in other parts of the country, some people resented the requirements for social distancing. After Greenwich closed its beaches and parks, Thomas Byrne, who holds Prescott Bush’s old job as moderator of the Greenwich town council, told the local media that the government’s measures were “the greatest assault on our freedom in my lifetime,” adding, “Why we don’t have a revolution in the streets escapes me.”
Not everyone was ready to stand on principle, though. As stock markets sank, the investor Cliff Asness reconsidered his objections to government aid. On Twitter, he made a series of “economic suggestions that kind of hurt me to admit,” he wrote. “We need, and I don’t think I’ve ever said this before, fiscal help. We need fiscal relief for individuals and small (and maybe large) businesses.” Anticipating the charge of hypocrisy, he wrote, “Yes, I’m losing libertarian bonafides here. I’m ok with that.” When the President eventually signed a relief bill, in March, it included a tax deduction, mostly for hedge funds and real-estate businesses, that was worth an average of $1.7 million for each of America’s forty-three thousand wealthiest taxpayers and cost the Treasury about ninety billion dollars in the first year.
In various ways, the virus confronted Americans with the result of a generation’s worth of political decisions. Even on the Gold Coast, the virus exposed cracks in the economic foundation; in Greenwich, municipal employees have been scrambling to provide emergency meal deliveries to some seven hundred families a week. Alan Barry, the town official, told me, “Greenwich represents two Americas. The haves and have-nots are literally separated and do not mix.”
Most of all, the virus seemed to magnify the central issue running through America’s discussions of wealth and fairness: How, exactly, would a fractured country define its understanding of the public good? Who are Americans ready to help? And who are we willing to ignore?
Few people in Greenwich have more reason to consider these questions than Michael Mason, who serves as the chairman of the town finance board, a sterile-sounding job with vast authority over daily life. He presides over discussions on how much to spend on special education, on poverty programs, and on the teaching of English as a second language. Last week, despite public protests from parents and students, Mason cast the deciding vote in favor of deep cuts to the town’s education budget, citing the economic effects of the pandemic.
Mason is tall, with parted silver hair and an earnest zeal for discussions of budgets and civic minutiae. His father flew a plane in the Second World War, and his two older brothers fought in Vietnam. Mason grew up in town, worked in the family aviation business, and volunteered as a fireman, before owning a branch of Million Air, a company that serves the private-jet industry.
He is also perhaps the town’s earliest Trump supporter. He attended the campaign announcement in which Trump descended a golden escalator and promised to build a wall against “rapists” from Mexico. “I’m friends with the family,” he told me. He met Trump’s sons Don, Jr., and Eric through a conservation club for hunters in Chappaqua, New York. They invited him to the Convention, in case they needed votes to thwart a challenge from within the Party. “I’m not going to run south under political pressure,” Mason said. Later, he joined them for private celebrations on Election Night and Inauguration Day.
Mason knows that the President’s “culture” still upsets many people in Greenwich. But, he said, “his policies over the last three years have gained more attention and probably more support.” He predicts that the trauma of the pandemic will persuade some voters that Trump was right to want to cut immigration and lure back industries from abroad. “He had policies that he wanted to change on our borders, on immigration. I certainly think people in this country now are worried about that.”
With the economy in crisis, Mason suspects that Trump will succeed in turning any rebound into a political asset. “There are people in the town right now—I guarantee you—who are saying, ‘Wow, this happened to me in ’08. My 401(k) went from X down to Y,’ ” he said. “What is Donald Trump telling you? ‘We’re going to do everything we need to so it does not take ten years to get you back where it was.’ I haven’t heard Joe Biden say that.”
Eventually, we wound our way to the inevitable question: How do you make your peace with Trump? His behavior toward women and immigrants? His separation of children from parents at the border? The “shithole” countries? Mason listened calmly. “I have no control over that,” he said. “What I have control over is what I worry about—the health and safety of my family, financial security of my family.” I pressed him, but he didn’t budge. “I’ve been empowered to care about the financial administrative affairs of a municipality with sixty thousand people sleeping at night,” he said. “I care about them.”
As Americans have reckoned with the origins of our political moment—the Trump years, the fury on all sides, the fraying of a common purpose—we have tended to focus on the effects of despair among members of the working class who felt besieged by technology, globalization, immigration, and trade. But that ignores the effects of seclusion among members of the governing class, who helped disfigure our political character by demonizing moderation and enfeebling the basic functions of the state. We—or they, depending on where you stand—receded behind gracious walls.
On the ground where I grew up, some of America’s powerful people have championed a version of capitalism that liberates wealth from responsibility. They embraced a fable of self-reliance (except when the fable is untenable), a philosophy of business that leaches more wealth from the real economy than it creates, and a vision of politics that forgives cruelty as the price of profit. In the long battle between the self and service, we have, for the moment, settled firmly on the self. To borrow a phrase from a neighbor in disgrace, we stopped worrying about “the moral issue here.” ♦