Trump Derangement Syndrome? 4 Leading Lawyers Who Lost It Defending The Donald

Look on their wrecked reputations, ye Mighty, and despair.

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Last Monday, court documents revealed that the 2020 presidential campaign of Donald J. Trump had prepared an internal memo debunking many of the outlandish claims that Trump relied upon in claiming the election was stolen from him. Despite that memo, Trump lawyers held a now-infamous news conference a few days later, on November 19, 2020, laying out their crazy conspiracy theory. The gist of the theory: Dominion Voting Systems, a voting-machine company, and Smartmatic, an election-software company, worked together and with others, including George Soros and Hugo Chávez, to steal the election from Trump.

Why did these lawyers engage in such seemingly irrational action? Trump Derangement Syndrome.

Hold on a sec, you say. Isn’t Trump Derangement Syndrome (TDS) an ailment afflicting Trump-loathing liberals?

It’s true that the classic presentation of TDS targeted Democratic strongholds across the country, from Berkeley to Cambridge to the Upper West Side of Manhattan. Here’s a good definition of TDS (via Chris Cillizza): “a mental condition in which a person has been driven effectively insane due to their dislike of Donald Trump, to the point at which they will abandon all logic and reason.”

This article identifies a new, more virulent strain of the syndrome. Patients who contract it are driven insane not by their dislike of Donald Trump but by their defense of him, and they come from a discrete and distinct demographic: once-respected conservative lawyers, whose fervor for Trump causes them to go cuckoo.1

Now is an opportune time for discussion and diagnosis. In addition to release of the Trump campaign’s internal memo, last week also brought news of another memo, by conservative law professor John Eastman, outlining how Vice President Mike Pence could have declared Trump the winner of the 2020 presidential election. As discussed below, Professor Eastman had one of the very worst cases of TDS.

Before diving into case studies of four intelligent and impressive lawyers who contracted severe TDS, here are some quick notes on my diagnostic criteria:

  • I’m excluding lawyers who maintained some semblance of sanity while supporting Trump, like attorney general Bill Barr, Senator Ted Cruz (R-Tex.), and Senator Josh Hawley (R-Mo.). Barr used Trump to advance his expansive view of presidential power and Catholic conservatism, while Senators Cruz and Hawley appear to have supported Trump out of political self-interest. Self-serving? Sure. TDS? No.

  • I’m also excluding lawyers who defended Trump but whose support is consistent with their pre-Trump selves. So Harvard law professor Alan Dershowitz isn’t on this list; his defense of Trump during the first impeachment reflects Dersh’s pre-existing contrarian streak—or commitment to principle, in Dershowitz’s telling—and not TDS.

  • Finally, I’m focusing on lawyers from elite legal backgrounds—a group that doesn’t include Jenna Ellis and L. Lin Wood, two lawyers who played prominent roles in challenging the 2020 election results on Trump’s behalf. They’re noteworthy in their own ways, but not the focus of this particular piece.

Without further ado, here they are: four leading lawyers who lost it defending the Donald—and what we can learn from their descents into delirium.


1. JEFFREY BOSSERT CLARK

Pre-Trump respectability: Jeffrey Clark has compelling credentials. After graduating from Harvard College and Georgetown Law, he clerked for a highly regarded jurist, Judge Danny J. Boggs (6th Cir.). From 1996 to 2001, Clark worked at Kirkland & Ellis, one of Biglaw’s most prestigious and profitable firms, where he made partner. From 2001 to 2005, Clark served as a deputy assistant attorney general in the Environmental and Natural Resources Division (ENRD) of the U.S. Department of Justice (DOJ). He then returned to Kirkland as a partner, working at the firm until he was nominated by President Trump and confirmed by the Senate to serve as the top lawyer—assistant attorney general—at the ENRD.

Hints of future lunacy: Not much. Yes, Clark could be pushy and power hungry; former DOJ colleagues told me about how he often tried to get in on high-level meetings, whether or not they involved his portfolio. But “pushy and power hungry” isn’t the same as “willing to overthrow the Republic”; if it were, half of D.C. lawyers would have been involved in the events of January 6. Instead, Clark was viewed as “unassuming,” even “nerdy.” His friend and former colleague Ted Frank described him to the New York Times as “a rumpled, thoughtful lawyer who is an intellectual—not a Machiavellian backstabber.”

Trump-driven descent into madness: Alas, “Machiavellian” is what Clark allegedly became. According to the Times, he conspired with Trump in a frankly bizarre scheme in which Trump would fire Clark’s friend and former Kirkland partner, Jeffrey A. Rosen, as acting attorney general, then install Clark in the role. As acting attorney general, Clark would then use the power of the DOJ to try and force Georgia state lawmakers to overturn their state’s 2020 presidential election results. The plot was foiled only when Jeffrey Rosen and other top DOJ officials threatened Trump with a 2021 “Saturday Night Massacre,” declaring that they would resign en masse if Trump and Clark went proceeded with their plan.

Derangement score: 6. Why only a 6? It’s all relative. Unlike the others on this list, Clark never publicly spouted conspiracy theories involving rigged voting machines or dead dictators, nor did he appear in a court or lie to a judge in his pro-Trump advocacy. [UPDATE (10/3/21, 9:18 a.m.): From a reader who knows Clark personally: “As much as I like Jeff Clark, you may have gone easy on him, as you failed to mention his email suggesting China was using WiFi-enabled thermostats to hack election equipment.”]

Where is he now: Clark landed on his feet. Although he didn’t make it back into Biglaw, he did find gainful new employment. In July, Clark was hired as chief of litigation and director of strategy at the New Civil Liberties Alliance (NCLA), a prominent, right-of-center legal group that fights alleged overreach by the administrative state.

2. JOHN C. EASTMAN

Pre-Trump respectability: John Eastman’s legal resume is even more glittering than Jeff Clark’s. Eastman earned a law degree from the University of Chicago Law School, where he served on the law review, and a Ph.D. in government from the Claremont Graduate School. He clerked for Judge J. Michael Luttig (4th Cir.)—one of the most prestigious judges to clerk for at the time, with a nearly unblemished record as a Supreme Court “feeder judge”—followed by Justice Clarence Thomas. After a short stint at Kirkland & Ellis, Eastman entered academia, joining the faculty of Chapman University Fowler School of Law in 1999. He served as dean of Chapman Law from 2007 until 2010, when he stepped down to run (unsuccessfully) for California Attorney General.

Hints of future lunacy: Eastman has long questioned birthright citizenship, the almost universally held notion that being born in the United States makes you a U.S. citizen. Eastman’s position is regarded as something of a fringe position, to put it charitably—which is why a Newsweek op-ed he wrote in August 2020, questioning Kamala Harris’s ability to serve as vice president based on his theory, generated a huge uproar and an apology from Newsweek.

Trump-driven descent into madness: Eastman began by representing Trump in Texas’s (doomed) attempt to get the Supreme Court to intervene in the election. When that didn’t work, Eastman urged Vice President Mike Pence to overturn the election results, arguing that Pence had such power as president of the Senate, overseeing the Electoral College count.2

Finally, when that failed—with his old boss, Judge Luttig, calling him out on Twitter—Eastman spoke the very next day at the January 6 “rally” in Washington. In his rambling remarks, he alleged without evidence that “secret folders” hidden inside voting machines were used to cast pro-Biden votes on behalf of registered voters who never cast their ballots.

Derangement score: 9. Watch the video of his unhinged speech on January 6. ‘Nuff said.

Where is he now: In January of this year, Eastman retired amid controversy from the Chapman faculty, after students, colleagues, and members of the board of trustees called for his ouster.

I can also confirm that, as recently discussed on Twitter, Eastman is no longer the chair of the Federalism and Separation of Powers practice group of the Federalist Society, the powerful organization of conservative and libertarian lawyers. As a source familiar with the situation told me, his departure “was vaguely in the works last fall, just a new-blood thing because Eastman is basically retired.” But after January 6, “FedSoc didn’t want to look like they were reacting to pressure, so they slow-rolled it.” (Shortly after Eastman’s involvement in the events of January 6, I called for him to be removed from his leadership role within FedSoc, so I’m glad to see that it finally happened.)

3. RUDOLPH W. GIULIANI

Pre-Trump respectability: Rudy Giuliani graduated cum laude from NYU Law School, where he served on the law review, and clerked for Judge Lloyd Francis MacMahon (S.D.N.Y.). Following his clerkship, he became a federal prosecutor in Manhattan—and fueled by courtroom successes, he enjoyed a meteoric rise. In 1981, just 13 years after graduating from law school, he joined the Reagan Administration as associate attorney general, the third-highest job at the Justice Department. Two years later, in 1983, Giuliani became the U.S. Attorney for the Southern District, an exceedingly prestigious and powerful post. As Manhattan’s top federal prosecutor, he made a name for himself by successfully pursuing organized-crime figures, corrupt politicians, and Wall Street titans like Michael Milken and Ivan Boesky.

Giuliani parlayed this prosecutorial prowess into a successful political career, serving two terms as mayor of New York City (1994-2001). He claimed victories in lowering crime, cleaning up the city, and making it more business-friendly, but the most celebrated part of his mayoralty was his leadership in the wake of the 9/11 attacks. This made him into a national hero, “America’s Mayor,” Time’s 2001 Person of the Year, and even a presidential frontrunner.

In between and following his stints in government, Giuliani worked for several distinguished Biglaw firms, including Patterson Belknap (as an associate) and White & Case (as a partner). In 2005, he joined Bracewell & Patterson, which became Bracewell & Giuliani after his arrival, to launch its New York office. In 2016, he left Bracewell for Greenberg Traurig, an even bigger Biglaw firm. He led GT’s cybersecurity and crisis management group until resigning in 2018, so he could focus on representing Trump in special counsel Robert Mueller’s Russia investigation.

Hints of future lunacy: Despite all of Giuliani’s professional success, over the years he exhibited moments of carelessness, arrogance, and tone-deafness—three qualities reflected in his hot mess of a personal life. His first marriage was annulled after he discovered that his wife was his second cousin. He announced the end of his second marriage at a press conference—which came as news to his then-wife, Donna Hanover. His third marriage—to Judith Nathan, his suspected paramour while he was still married to Hanover—ended in a train wreck of a divorce.

There was also his infamous rant against ferrets. And this (warning: viewer discretion advised).

Trump-driven descent into madness: Giuliani enthusiastically supported Trump during the 2016 presidential election, hoping to be appointed as Secretary of State, which never happened. But he remained in Trump’s orbit, defending the president in the Mueller investigation and getting involved in the Ukraine mess, urging the Ukrainian government to investigate dubious conspiracy theories involving then-candidate Joe Biden and his son Hunter Biden.

Where Giuliani really went off the deep end, though, was when he sprang into action after Trump’s loss in the November 2020 presidential election. Giuliani was the public face of the self-proclaimed “elite strike force” that challenged the election results on behalf of Trump—and lost almost every lawsuit that it filed.

Appearing in court personally, Giuliani wet the proverbial bed. Asked by Judge Matthew Brann (M.D. Pa.) what standard of review should apply to his claims, a basic question that any litigator (or first-year law student) could have answered, Giuliani replied, “the normal one.” As a young prosecutor, Giuliani once cross-examined a corrupt politician so skillfully that the defendant left the stand and then pleaded guilty—so it was pathetic to see him crash and burn like this.

Giuliani’s efforts on behalf of Trump culminated not just in humiliation for Giuliani, but also suspension of his law license. In June, New York State’s Appellate Division, First Department, issued a 33-page decision condemning the “demonstrably false and misleading statements” that Giuliani made while litigating the election challenges, concluding that they “directly inflamed tensions that bubbled over into the events of January 6.”

Derangement score: 8. I was tempted to give Giuliani a 9, but when you compare his January 6 speech to that of John Eastman, Eastman’s is a trifle more cray-cray. And Giuliani was never quite as insane as Sidney Powell, from whom he quickly distanced himself—saying, in essence, “I might be crazy, but I’m not that crazy.”

Where is he now: No lawyer on this list—or in America—has fallen as far as Rudy Giuliani. As the 20th anniversary of the 9/11 attacks recently reminded us, he was once a national hero. Now, he’s a national joke, mocked even in Trumpworld—America’s Mayor turned America’s Laughingstock, suffering a literal meltdown while holding a press conference in the parking lot of Four Seasons Total Landscaping, a Philadelphia landscaping company across the street from a crematorium and next door to a porn store.

Incredibly enough, Giuliani might have farther to fall. On the civil side, he faces defamation lawsuits from Dominion Voting Systems and a former Dominion employee that seek more than $1 billion in damages. On the criminal side, the former U.S. Attorney for the Southern District finds himself under investigation by his former office for his shady Ukraine dealings. I’m not sure that he’ll ultimately get indicted, but even the possibility of an indictment is shocking.

4. SIDNEY POWELL

Pre-Trump respectability: A native of North Carolina, Sidney Powell graduated from UNC Chapel Hill, her state’s flagship public university, in less than two years. Immediately after earning her law degree at the University of North Carolina School of Law, a top-25 school, she landed a prestigious position as an assistant U.S. attorney (AUSA)—and she was quite possibly the youngest federal prosecutor in the country at the time. Powell focused on appellate work, one of the most intellectual specialties in litigation, eventually rising to serve as the appellate section chief in the Western District of Texas and then the Northern District of Texas. Her resume might not dazzle as much as those of the other lawyers on this list, but it’s undoubtedly estimable.

After serving as an AUSA for about a decade, Powell moved into white-collar criminal defense work. In 2014, she wrote a book about prosecutorial misconduct, Licensed to Lie: Exposing Corruption in the Department of Justice. Today prosecutorial misconduct is covered extensively in the media, and several young, up-and-coming district attorneys have even made dealing with it a cornerstone of their campaigns. But at the time that Powell wrote Licensed to Lie, prosecutorial misconduct wasn’t on the radar of many. Her well-received book brought attention to the issue, especially in conservative circles, perhaps thanks to her criticism of the prosecution of the late Senator Ted Stevens (R-Alaska).3

Hints of future lunacy: In Licensed to Lie, Powell dwells at length on the prosecution of one client of hers, Merrill Lynch executive James Brown, who was convicted of crimes related to the collapse of energy giant Enron. Her discussion of the case, blaming her loss on prosecutorial misconduct, borders on paranoid and obsessive.

Her most well-known work as a defense lawyer was representing Michael Flynn, former national security advisor to President Trump. She adopted a scorched-earth legal strategy in which she moved for dismissal of his prosecution (after he had already pleaded guilty), alleged a “deep state” conspiracy against her client, and claimed rampant prosecutorial misconduct. Her approach to the case struck many observers as unorthodox, if not downright crazy.

But it made her a hero on the right, and in Trumpworld, it actually worked. First the Justice Department, under attorney general Bill Barr, moved to dismiss the case, in a move that many saw as politically motivated. After that didn’t bring immediate results, thanks to resistance from Judge Emmett Sullivan (D.D.C.) and the D.C. Circuit, Trump straight-up pardoned Flynn. So Powell’s seemingly crazy strategy wound up being… crazy like a fox.

Trump-driven descent into madness: Oh goodness, where to begin? Sidney Powell appeared alongside Rudy Giuliani at the notorious November 19 press conference, but a few days later she got dumped from the “elite strike force,” apparently because she was too crazy even for them.

Working independently from Giuliani, Powell promised bombshell revelations about election fraud that she infamously compared to the kraken, “a legendary sea monster of gigantic size and cephalopod-like appearance in Scandinavian folklore.” Dominion, Smartmatic, the liberal billionaire George Soros, the former (and dead) Venezuelan dictator Hugo Chávez, the Clinton Foundation, Cuba, China—is there anyone who wasn’t involved in Powell’s elaborate conspiracy theory?

Powell’s craziness came at a cost. Last month, Judge Linda V. Parker (E.D. Mich.) sanctioned Powell, Lin Wood, and seven other pro-Trump lawyers, declaring that their challenge to Michigan’s election results was “a historic and profound abuse of the judicial process.” Judge Parker ordered them to pay the attorneys’ fees for the defendants in the case, the city of Detroit and the state of Michigan, and to undergo continuing legal education (ouch). She also referred them to local authorities in their home states for possible suspension or disbarment—which means that Powell could end up losing her own law license over lies.4

Derangement score: 10. #ReleaseTheKraken, or #ReleaseTheCrackpot? Of all the lawyers on this list, Powell advanced the most detailed—and therefore most deranged—theories about the election.

Where is she now: Good question. For a time Powell was hard to find, perhaps because she was trying to avoid being served with the billion-dollar defamation lawsuit filed by Dominion Voting Systems. But she recently bought a former antique store in Alexandria, Virginia, just outside of D.C., which she plans to use as a law office—suggesting that we haven’t heard the last of Sidney Powell and Team Kraken.


What can we learn from these four lawyers and their serious cases of Trump Derangement Syndrome? Here are some thoughts.

First, a stellar CV doesn’t inoculate you against TDS. It wasn’t just low-information voters and baskets of deplorables who came to fervently believe that the election was stolen. Just look at the pedigrees of the four attorneys we’ve just analyzed—graduates of top colleges and law schools, former clerks to federal judges (and even a Supreme Court justice), former federal prosecutors, former law professors, and former partners at major firms. Given my own weakness for elite credentials, this has been a salutary reminder for me that there’s a difference between “smart” and “good,” and there’s a difference between “stupid” and “crazy”—with TDS being about the latter, not the former.

Second, far from being immune to TDS because of their brilliance, highly accomplished attorneys might be more susceptible to the disease. Why? It has to do with what made them successful as lawyers.

When I went from being a law clerk to a litigator years ago, I had to change my mindset from arbiter to advocate. For my first few months as a law firm associate, I’d say things to the partners like, “This is a close case, but I think our opponents have the better argument.” But impartially evaluating arguments was no longer my job; my job was to advocate zealously for my clients. Over time, I noticed that the best litigators were ones who believed deeply in their arguments—whether because they believed in them all along or had convinced themselves of them along the way.

Talented litigators use their intellect and creativity to develop arguments on behalf of clients, and to present those arguments most effectively, litigators need to believe them. Part of being a great litigator is drinking the proverbial Kool-Aid. This form of motivated reasoning is adaptive for litigators, helping them do their jobs. The problem is that if taken too far or applied to meritless claims, it can lead to disastrous consequences—as it did in the case of the Trump election challenges.

Third, addiction to attention and adoration is a dangerous thing. If there’s something these four lawyers share in common, it’s a love of the limelight. Many of them had a taste of it from past experiences—Giuliani from his time as a prosecutor and in politics, Powell from her book and her work on the Flynn case—and they got hooked. Their desire to remain relevant, even (or especially) as their Trumpian meal ticket was getting shredded, likely fueled their descent into madness.

Fourth, the legal community needs to think long and hard about how to relate to this quartet of disgraced lawyers. How they are treated in the wake of their actions reflects not just on them, but on the legal profession as a whole. What consequences should these attorneys face for their actions? Should these TDS-suffering lawyers be quarantined? I’m no fan of “cancel culture,” but these are legitimate questions.

Human psychology being what it is, there’s nothing we can do to prevent high-powered lawyers—or anyone else—from being corrupted by ambition and vanity. But guided by cautionary tales like today’s, we can try our best to ensure that Trump Derangement Syndrome or the next disease like it threatens only individuals, not our entire justice system and the rule of law.

[UPDATE (10/3/21, 9:18 a.m.): For additional discussion, check out this episode of All the Presidents’ Lawyers, where I spoke with Ken White about this story.]


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1

To be clear about where I’m coming from, and as I’ve mentioned before, I might be considered conservative when it comes to legal and jurisprudential matters. And true conservatives believe deeply in the Constitution and the rule of law—values that were threatened by Trump’s unsuccessful attempt to hijack the 2020 election.

2

Eastman’s memo to Vice President Pence has been criticized on both sides of the aisle. For example, Professor Jonathan Adler, a leading right-of-center legal academic, explained the flaws in Eastman’s analysis and declared the memo to be “poor lawyering for a disreputable cause.”

3

I interviewed Sidney Powell about Licensed To Lie back in 2014, and I found her to be smart, thoughtful, and seemingly sane. Near the end of the interview, I asked her whether she would continue to practice law, given her disillusionment with the legal system. Her response: “I don’t know about continued practice. I still have my law office and active cases, but I’m not sure what I will do after I finish those.” Little did we know….

4

According to Peril, the new book by Bob Woodward and Robert Costa, we were saved from more Sidney Powell by… Rudy Giuliani’s ego. Not only did Giuliani boot her from the official Trump legal team, but after Trump floated the idea of somehow appointing Powell to serve as a “special counsel” investigating election fraud, Giuliani shot down the idea.