George Conway: Why Trump had to hire this legal odd couple

This is what happens when you don’t pay your legal bills.

President Trump, whose businesses and now campaign have left a long trail of unpaid bills behind them, has never discriminated when it comes to stiffing people who work for him. That includes lawyers — which is part of the reason he found the need to make some curious last-minute tweaks to his team, announcing the addition of the legal odd couple of Alan Dershowitz and Kenneth W. Starr.

​The president has consistently encountered difficulty in hiring good lawyers to defend him. In 2017, after Robert S. Mueller III became special counsel, Trump couldn’t find a high-end law firm that would take him as a client. His reputation for nonpayment preceded him: One major Manhattan firm I know had once been forced to eat bills for millions in bond work it once did for Trump. No doubt other members of the legal community knew of other examples.

Of course, being cheap wasn’t the only reason Trump struck out among the nation’s legal elite. There was the fact that he would be an erratic client who’d never take reasonable direction — direction as in shut up and stop tweeting. Firms also understood that taking on Trump would kill their recruiting efforts: Top law students of varying political stripes who might be willing, even eager, to join a firm that provides pro bono representation to murderers on death row, want nothing to do with Trump.

Independent counsel Kenneth Starr testifies before the House Judiciary Committee during Bill Clinton's impeachment inquiry in November 1998. (Luke Frazza/AFP via Getty Images)
Independent counsel Kenneth Starr testifies before the House Judiciary Committee during Bill Clinton’s impeachment inquiry in November 1998. (Luke Frazza/AFP via Getty Images)

That left Trump to be personally defended in the Mueller investigation by a random patchwork of counsel, including Jay Sekulow, a lawyer specializing in religious liberty cases, and John Dowd, a Washington solo practitioner who, according to Bob Woodward, viewed Trump as a “f—ing liar.” (Dowd denies that.) Last but not least, Trump had the assistance of Rudolph W. Giuliani — who has done more than anyone other than Trump himself to get Trump impeached.

Contrast that unimpressive crew with the team assembled by President Bill Clinton, who had not one, but two, top-notch law firms defending him: global powerhouse Skadden Arps, with heavy-hitter Bob Bennett, to handle the Paula Jones case; and the elite Washington defense firm, Williams & Connolly, led by the brilliant David Kendall, to handle the Whitewater investigation, its Monica Lewinsky spinoff and impeachment.

Precisely because he never had a defense team truly suited for the task at hand, Trump found the need now to add to the mix. But the mix still makes no sense. On the team, as of Friday, are the legal odd couple of Harvard Law School professor emeritus Dershowitz and former federal appeals court judge Starr.

It’s hard to see how either could help.

Dershowitz gets specific about his ‘limited role’ in Trump impeachment
Havard law professor emeritus Alan Dershowitz spoke Jan. 19 about his role on the president’s legal team after Trump picked him, personally. (Video: Meg Kelly/Photo: Jabin Botsford/The Washington Post)

Dershowitz may be a genius in some ways, but he’s not necessarily the advocate you want on your side. Judges have told me they find him condescending in manner and tone — not the approach you want before a court consisting of 100 U.S. senators. And he’s wont to make off-the-wall arguments. As his former Harvard colleague Professor Laurence Tribe has put it, Dershowitz “revels in taking positions that ultimately are not just controversial but pretty close to indefensible.” Dershowitz’s recent assertion that the Supreme Court could order the Senate not to conduct an impeachment trial illustrates the point. Not only is that claim indefensible — it’s also ridiculous.

And then there’s Starr. I know and like Starr, but I can’t comprehend what he’s doing here. He’s best known as the independent counsel whose investigation led to the impeachment of Clinton. That’s hardly helpful for Trump, because Clinton was a piker compared with Trump.

Clinton’s core offense was to obstruct a private civil action about pre-presidential conduct and cover up sexual misconduct — none of which had involved abuse of presidential power. From a constitutional standpoint, that’s a trifle compared with extorting a foreign nation by cutting off federal military funds in an effort to interfere with an upcoming U.S. presidential election.

How one of the Senate’s most vulnerable Democrats approaches impeachment
Sen. Doug Jones (D-Ala.) is facing a tough reelection. He says that has nothing to do with how he is preparing for the Senate’s impeachment trial. (Rhonda Colvin, Ashleigh Joplin/The Washington Post)

As if that were not enough, in the Clinton case, Starr argued that Clinton had committed an impeachable offense by blocking witness testimony and documents. Oops.

Any litigator will tell you that adding to your legal team on the eve of trial most likely will not produce better lawyering but, rather, chaos. In that sense, at least, Trump will be getting the representation he deserves.

Read more:

In Business and Governing, Trump Seeks Victory in Chaos

Three decades ago, Donald J. Trump waged a public battle with the talk show host Merv Griffin to take control of what would become Mr. Trump’s third Atlantic City casino. Executives at Mr. Trump’s company warned that the casino would siphon revenue from the others. Analysts predicted the associated debt would crush him.

The naysayers would be proved right, but throughout the turmoil Mr. Trump fixated on just one outcome: declaring himself a winner and Mr. Griffin a loser.

As president, Mr. Trump has displayed a similar fixation in his standoff with Congress over leveraging a government shutdown to gain funding for a wall on the Mexican border. As he did during decades in business, Mr. Trump has

  • insulted adversaries,
  • undermined his aides,
  • repeatedly changed course,
  • extolled his primacy as a negotiator and
  • induced chaos.

He hasn’t changed at all,” said Jack O’Donnell, who ran a casino for Mr. Trump in the 1980s and wrote a book about it. “And it’s only people who have been around him through the years who realize that.”

..Mr. Trump was expected to sign off on the deal, but then came the suggestion from conservative critics that he had caved in to Democrats — that he was a loser. It was a perception Mr. Trump could not bear, and he quickly reversed course.

He also reverted to lifelong patterns in business. People who worked with him during those years say they see multiple parallels between Mr. Trump the businessman and Mr. Trump the steward of the country’s longest government shutdown.

His lack of public empathy for unpaid federal workers echoes his treatment of some construction workers, contractors and lawyers whom he refused to pay for their work on his real estate projects. The plight of the farmers and small-business owners wilting without the financial support pledged by his administration harks back to the multiple lenders and investors who financed Mr. Trump’s business ventures only to come up shortchanged.

And his ever-changing positions (I’ll own the shutdown; you own the shutdown; the wall could be steel; it must be concrete; then again, it could be steel) have left heads in both parties spinning. Even after his televised proposal on Saturday to break the deadlock, Mr. Trump has no progress to show.

That book, published in 1987, was intended to be an autobiography of Mr. Trump, who was 41 at the time. Mr. Schwartz said that he created the idea of Mr. Trump as a great deal maker as a literary device to give the book a unifying theme. He said he came to regret the contribution as he watched Mr. Trump seize on the label to sell himself as something he was not — a solver of complicated problems.

Rather, Mr. Schwartz said, Mr. Trump’s “virtue” in negotiating was his relentlessness and lack of concern for anything but claiming victory.

If you don’t care what the collateral damage you create is, then you have a potential advantage,” he said. “He used

  • a hammer,
  • deceit,
  • relentlessness and
  • an absence of conscience

as a formula for getting what he wanted.”

In a brief telephone interview on Sunday, Mr. Trump was not specific in defending his tactics, but he described himself as successful in his chosen fields of real estate, entertainment and finally politics. “I ran for office once and I won,” Mr. Trump said.

The president’s supporters say he gets an unfair rap as a poor negotiator, saying that his style and unusual approach — and unwillingness to accept defeat even in the worst situations — have often had positive results. And in a Washington that doesn’t like outsiders, he has clearly forced his adversaries out of their comfort zones.

“President Trump’s success in business has translated into success as president,” Sarah Huckabee Sanders, the White House press secretary, said. “He’s

  • ignited a booming economy with
  • rising wages and
  • historically low unemployment,
  • negotiated better trade deals,
  • persuaded our allies to contribute their fair share to NATO, and
  • secured the release of American hostages around the world.”

.. The bank eventually settled with Mr. Trump, saving him from having to pay the $40 million. Mr. Trump expressed his gratitude to the lawyer who fought on his behalf by not fully paying his bill. “He left me with some costs,” said the lawyer, Steven Schlesinger.

From the time he built his first Manhattan apartment building, Mr. Trump left a string of unpaid tabs for the people who worked for him.

The undocumented Polish workers who did the demolition work for that first building, Trump Tower, eventually won a $1.375 million settlement. Since then, scores of lawyers, contractors, engineers and waiters have sued Mr. Trump for unpaid bills or pay. Typically, he responds by asserting that their work did not meet his standard.

That might sound familiar to furloughed federal workers. Mr. Trump recently retweeted an article, attributed to an anonymous senior official in his administration, arguing that 80 percent of federal workers do “nothing of external value” and that “furloughed employees should find other work, never return and not be paid.”

Mr. Trump has claimed, without evidence, that “maybe most” federal workers going without pay are “the biggest fan” of his use of the shutdown to fund a border wall. In ordering thousands back to work without pay, he has put the pain for the shutdown on them.

Mr. Trump has also embraced his business practice of giving the most latitude and trust to family members, no matter their prior experience.

He put his first wife, Ivana, a model, in charge of an Atlantic City casino and the Plaza Hotel in Manhattan. He put his younger brother, Robert, who had some background in corporate finance, in senior positions at the casinos. Not long after three of his children graduated from college, he vested authority in them over golf courses, hotels and licensing deals.

.. In the White House, Mr. Trump has increasingly leaned on his son-in-law, Jared Kushner, for guidance on dealing with Congress amid the current stalemate. Mr. Kushner, who like Mr. Trump is the son of a wealthy real estate developer, has not always impressed old hands on Capitol Hill.

.. With Democrats now in charge of the House of Representatives, Mr. Trump also has a new set of adversaries, and other old habits from his years in business have re-emerged.

Through his Twitter feed, he has verbally pummeled Senator Chuck Schumer, the minority leader, and tried to drive a wedge between Mr. Schumer and his fellow Democrat, Speaker Nancy Pelosi.

.. Barbara Res, who said she enjoyed much about working for Mr. Trump as a construction executive in the 1980s and 1990s, sees in Ms. Pelosi a new challenge to Mr. Trump’s lifelong tactics. One blind spot she observed was that Mr. Trump “believes he’s better than anyone who ever lived” and saw even the most capable of women as easy to run over.

“But there was never a woman with power that he ran up against, until Pelosi,” she said. “And he doesn’t know what to do with it. He’s totally in a corner.”

In the interview, Mr. Trump described Ms. Res, Mr. O’Donnell and Mr. Schwartz as disgruntled workers whom he had shunted aside, who had experience with him for relatively brief periods and who were simply using his name for attention.

During his years in business, Mr. Trump rarely displayed an interest in details or expert opinions that might have informed whether his plans would actually work. That pattern has also emerged in the shutdown dispute.

Thirty years ago, his claimed defeat of Mr. Griffin turned out to be a Pyrrhic victory.

Within months of completing construction on his third casino, the Trump Taj Mahal, he could not pay interest to the bondholders who had financed the project. Having overpaid and overleveraged himself on other deals, banks forced him to turnover or sell almost everything.

His wealthy father helped bail him out. But Mr. Trump blamed everyone else. He fired nearly all his top executives and stopped paying contractors who had built the casino.

In describing the border wall, Mr. Trump has expressed unending confidence in its efficacy. Others, including Representative Will Hurd, a Republican whose Texas district includes part of the border with Mexico, have described it as a tall speed bump, nearly useless without technology to spot illegal crossings immediately and dispatch border agents to quickly respond.

Mr. O’Donnell, the casino manager, said long-term consequences never concerned Mr. Trump. He was always willing to pay too much in order to get a deal signed so he could declare victory, he said.

“He just wants to get the deal,” Mr. O’Donnell said.

Donald Trump Just Cannot Help It

The Reichstag fire was at least a fire. Here, there is smoke and mirrors.

When Trump was in business, his shtick was stiffing contractors. If confronted, he would try some bombast and storm out of meetings, as he did the other day with congressional leaders, ending talks on the partial government shutdown caused by a crisis he has manufactured. His shtick now is stiffing all Americans. The technique is the same: Keep reality at a distance through hyperactive fakery.

.. A manufactured crisis, I said. It’s worth recalling the 5,200 troops ordered to the southern border before the midterm elections to confront the “caravan of migrants.” This was an exercise in manipulative illusion.

Monthly crossings over the southern border have declined in recent years. The number of migrants apprehended has also fallen over the past decade, with a recent tick upward. There is no humanitarian crisis, just as not a single mile of additional wall has been built since Trump took office.

But absent this noise, what does reality offer the president? Robert Mueller, Nancy Pelosi and Michael Cohen, the specters of his insomnia.

.. The essential distinction that Frankfurt, a professor of philosophy emeritus at Princeton University, makes is between lies and bull. As he writes, “It is impossible for someone to lie unless he thinks he knows the truth. Producing bullshit requires no such conviction.”

.. It is a habit “unconstrained by a concern with truth” whose essence is “not of falsity but of fakery.” The addict of bull “does not care whether the things he says describe reality correctly. He just picks them out, or makes them up, to suit his purpose.” He is “trying to get away with something.” His “focus is panoramic rather than particular,” and he shuns “the more austere and rigorous demands of lying.

Frankfurt’s conclusion may be read as an ominous verdict on this president. The bull merchant “does not reject the authority of the truth, as the liar does, and oppose himself to it. He pays no attention to it at all. By virtue of this, bullshit is a greater enemy of the truth than lies are.”

It has been said that Trump’s extraordinary election victory owed much to his intuitions about the anger in the heartland. There is some truth in this. But his essential intuition was into the readiness of Americans, suspended between the real and the virtual, for a post-truth presidency.

Quinta Jurecic, in an important essay for the Lawfare Blog, set out the dangers inherent in this shift before Trump took office. In the essay, “On Bullshit and the Oath of Office: The ‘LOL Nothing Matters’ Presidency,” she cited Frankfurt and argued that Trump’s “foundational disrespect for meaning and consequence” — that is to say, for reality and the very concept of law — would make it “impossible for Donald Trump to faithfully execute the laws of this nation and the duties of the oath of office and to preserve, protect, and defend the Constitution.”

The president’s apparent readiness to “do national emergency,” as he put it, over a manufactured border crisis amounts to a perfect illustration of this danger. The Reichstag fire was at least a fire. Here there is only smoke and mirrors.

I would add one element to the reflections of Frankfurt and Jurecic on bull. There may be something amusing, or at least innocuous, about the bullshit artists encountered in a lifetime. They may be waved away. But in Trump the element of sadistic cruelty in his personality (mocking the disabled, for example), and the sheer gall of his fakery, make of him a malignant, rather than a benign, bullshit artist. He happens to occupy the world’s most powerful office.

Trump cannot help himself, I said. He can’t and won’t. But as citizens, “we have a duty to insist that words have meaning,” as Jurecic writes. If they don’t, neither does the Republic. That’s what the ants told me as I gazed at them, troubled and fixated.