Were Trump's Lawyers Foot Soldiers or Ringleaders?

by Michael C. Dorf

“Ours is not a system of justice where foot soldiers go to jail and the masterminds and ringleaders get a pass." -- Rep. Jamie Raskin (D., Md.), member of House Select Committee to Investigate the January 6th Attack on the U.S. Capitol, Dec. 19, 2022.


In the first years of the current millennium, Vice President Dick Cheney received considerable assistance from talented attorneys who offered at best extremely tendentious arguments for the lawfulness of what Cheney and others in the George W. Bush administration euphemistically termed "enhanced interrogation"--thus greenlighting a policy of torture. The main lawyers involved in the effort--David Addington (as counsel to the VP and known as "Cheney's Cheney"), Jay Bybee (Bush's first head of the Office of Legal Counsel), and John Yoo (Bybee's deputy)--were investigated but not prosecuted for war crimes by a Spanish judge and ultimately suffered only modest reputational consequences at home. Indeed, in the ensuing two decades, they have thrived. Addington followed his stint in the Bush White House with a soft landing at the Heritage Foundation. Bybee is a (now-senior) judge of the U.S. Court of Appeals for the Ninth Circuit. Yoo holds a chair on the faculty of UC-Berkeley Law and is an unapologetic public intellectual.

The key lawyers involved in Donald Trump's effort to overturn the 2020 election included opera-buffa clowns Rudy Giuliani and Sidney Powell, comparable in stature and ability to Bush's first Attorney General, Alberto Gonzales (who was also instrumental in authorizing torture). But while Giuliani's "normal scrutiny" and Powell's absurd conspiracy theories drew the most attention, Trump also had the aid of three lawyers with abilities and pre-Trump credentials roughly comparable to those of Addington, Bybee, and Yoo. John Eastman is a former SCOTUS clerk and was dean of an ABA-accredited law school. Jeffrey Clark was a well-respected attorney in private practice and government. Kenneth Chesebro was a talented private practitioner (about which more below the jump).

What comes around goes around.  The lawyers who served VP Dick Cheney by justifying torture escaped any real accountability for their deeds. Soon-to-be-former Congresswoman Liz Cheney played a pivotal, honorable, and courageous role as the tip of the January 6 Committee spear, unflinchingly demanding accountability from Donald Trump and his fellow seditionists, including her GOP colleagues. The committee's report names, among others, attorneys Eastman, Clark, and Chesebro. Yet the report and accompanying referrals carry only so much weight as the Justice Department gives them--and even then, the wheels of justice turn sufficiently slowly that it is possible to imagine all of the Trumpists and Trump himself running out the clock. In the end, the lawyers and others in the cross-hairs of Cheney-fille could end up as unscathed as those who served Cheney-père.

I have crossed paths obliquely with each of the three lawyers in the Trump brain trust. Eastman was an occasional contributor to scholarly conversations in which I also engaged. One of his 2020 pre-election memos weirdly cited an analysis by Professors Laurence Tribe, Neil Buchanan, and me as ostensible support for one of Eastman's hare-brained schemes. I don't recall meeting Eastman, but I might have. In any event, prior to the 2020 election's aftermath, I would have thought of him as deeply conservative but not an enemy of democracy.

I have no recollection of meeting Clark either, but it's likely I knew him when we were both young. The Wikipedia entry for Clark says that he received his undergraduate degree in 1989 from Harvard, where he was a member of the parliamentary debate team. As a senior, I was president of that team in what would have been Clark's freshman year. As a law student, I was an unofficial coach of the team in what would have been his junior and senior years. I checked with a star debater from the class of 1989, who recalls Clark as being on the team. So I probably mentored him.

And then there's Ken Chesebro, who for some years worked as a lawyer for Prof Tribe on various matters that the latter undertook as an appellate litigator. For two of those years, I was one of Prof Tribe's student research assistants. Mostly I worked on scholarly projects, but I also performed some litigation-related research, including at least three projects with Chesebro. At the time, I thought highly of him as a skilled lawyer who shared the generally liberal values of Prof Tribe. But that was over thirty years ago. Obviously Chesebro went through some sort of transformation in the years since.

I offer the autobiographical information in the prior three paragraphs for the main purpose of underscoring that I have a sound basis for concluding that the failings of Eastman, Clark, and Chesebro were not for lack of smarts. To be sure, smart lawyers can do stupid things. As my colleague Prof. Brad Wendel astutely observed about the lawyers who authored the torture memos in the Bush administration:

The problem with the legal advice . . . is, in a word, that it was incompetent. This evaluation is often met with incredulity, because the lawyers involved were extremely capable, with sterling academic credentials. Talented lawyers can still produce incompetent legal analysis . . . . Given the uniform attitude of condemnation of all legal materials toward torture, including express non-derogation principles that block the appeal to a national emergency as a justification of torture, it is difficult to escape the conclusion that a narrow, technical parsing of the text of conventions and statutes, looking for loopholes, is a serious interpretive mistake. This is exactly what the OLC lawyers did, however, constructing tendentious arguments in support of the conclusion that American interrogators could repeatedly subject detainees to waterboarding, sleep deprivation, extreme cold temperatures, stress positions, sexually and religiously oriented humiliation, harsh lights and sound, and simulated attacks by dogs, without crossing the line into legally prohibited torture.

When smart lawyers say stupid things, it's usually because they are motivated to misread the law (a point with which Prof Wendel very much agrees). Thus, the failings of the Trump lawyers, like those of the Bush administration lawyers, were chiefly ethical failings.

Speaking of ethics, Professor Tribe was one of the many prominent signers of a letter to the relevant New York State attorney disciplinary authorities urging investigation of Chesebro for possible violations of his ethical obligations as a member of the bar. Depending on the decisions of the DOJ, Chesebro, Clark, and Eastman may have more to worry about than the possible loss of their ability to practice law.

Should they be subject to attorney discipline and/or criminal liability? Some actions taken under cover of a legal practice are just plain illegal. For example, actor Bob Odenkirk as attorney Saul Goodman/Jimmy McGill in Breaking Bad and the prequel Better Call Saul frequently engages in outright criminal behavior--serving as the bagman for drug deals or fraudulently altering documents. The fact that Goodman/McGill is a lawyer should not in any way immunize his conduct. If anything, it exacerbates his misdeeds.

However, as a general matter, I believe that the threshold should be very high for criminal prosecution of attorneys acting as attorneys in the sense of making arguments in court or giving legal advice. But very high does not mean infinitely high. At a minimum, even a lawyer who stays completely within the bounds of legal and ethical obligations is sometimes appropriately subject to what Prof. Wendel aptly calls "Lawyer Shaming" for taking on an extremely odious client (like Donald Trump) or cause (like Trump's defense in his impeachment trials).

Turning from social opprobrium to concrete consequences, we might usefully draw two distinctions. The first is between making arguments in court, before Congress, or in another public forum, and making them in private in the course of giving legal advice. A lawyer who makes a bad or even frivolous argument in a public adversary proceeding will, if opposed by competent counsel, achieve nothing for the client, because the weakness of the argument will be revealed. By contrast, a lawyer who gives confidential but unsound legal advice to a client who is legally unsophisticated and/or committed to an illegal plan that he wants to be told is lawful acts in the shadows. The authors of the torture memos and the lawyers who told Trump that there was a legal path to VP Mike Pence blocking the certification of the election labored in private--which ought to count heavily against them.

Second, we might distinguish between the law and the facts. Court rules (like Federal Rule of Civil Procedure 11) forbid lawyers from misrepresenting the law as well as the facts, but given the under-determinacy of the law in many settings, it is usually easier to establish (both for ethical sanctions and criminal liability) that a lawyer has misrepresented the facts than the law. As applied to the the Trump insurrectionist lawyers, that distinction makes a fair bit of sense. The Trump lawyers' argument that the Vice President has the unilateral authority to reject electoral slates is deeply flawed (especially given that in many elections the sitting Vice President is a candidate for re-election or the Presidency), but the argument is not entirely ruled out by judicial precedent (because there isn't any) or past practice. By contrast, the factual predicate for the Trumpist lawyers' gambit--that the fake electors or bogus charges of election fraud created anything resembling a genuine dispute over the validity of state certifications--was itself plainly fraudulent.

Accordingly, investigation and possible attorney discipline and/or criminal prosecution seem appropriate for these lawyers. In some circumstances, lawyers representing clients can be held accountable for failing to say no--for acting as loyal foot soldiers rather than as officers of the court. Accountability is all the more appropriate for lawyers who did not merely reluctantly acquiesce in dubious plans but displayed creativity in designing malevolent schemes to thwart democracy.