TPM Illustration/Getty Images/Ken Chesebro

Exclusive: Trump Lawyer Kenneth Chesebro Talks About His Role In The Runup To Jan. 6

The attorney who reportedly suggested that “‘wild’ chaos” would prompt Supreme Court justices to be more likely to intervene in the 2020 election has spoken exclusively with TPM about his representation of the Trump campaign during its efforts to overturn the election.

Kenneth Chesebro fielded extensive questions from TPM about his representation of the Trump campaign, about how he went from a liberal cause lawyer and protégé of Harvard Law Professor Larry Tribe to a Trump attorney, and about his views on the Jan. 6 Capitol insurrection. 

On several of the key questions that have emerged about his legal work for Trump, Chesebro was lawyerly, careful, and tightlipped in his responses. He was more forthcoming about his own background, how he came to be involved with the Trump campaign, and the criticisms that have come his way since he emerged as an early proponent of some of the Trump campaign’s most controversial strategies to overturn the 2020 election.

What emerges from hours of sitdown interviews is a picture of a man who was deeply involved at a high level in coordinating the Trump campaign’s strategy to overturn the election, who regrets the violence at the Capitol as self-defeating, and who wishes that more attention had been paid to the issues he raised.

“There was good reason to argue that under Article II, that Biden had not legitimately won the electoral votes,” Chesebro told TPM. “I’m not saying that Trump deserved to win in each state, I’m saying it was legitimate to argue under Article II that there was a problem.”

Chesebro said that he abhorred the violence of January 6, that it was “primarily a human disaster,” and that “it was the worst possible thing that could have happened in terms of lawyers that had serious concerns about the election in several states, that were never really addressed on the merits.”

Despite how well known the events between Election Day and Jan. 6 have become, Chesebro has flown largely under the radar, emerging only this year in a pair of New York Times stories as an important figure in the Trump campaign’s efforts. He plays second fiddle in the coverage to Trump lawyer John Eastman, but they knew each other before 2020, had worked together on an earlier case, and would reunite in the aftermath of Election Day. It was Chesebro who appears to have first advocated for alternate slates of electors with an eye on Jan. 6 as the make-or-break date for Trump. 

While Eastman has become a national figure, Chesebro has remained in the shadows. Until now.   

From Tribe Disciple to Trump Lawyer

While a student at Harvard Law School, Chesebro received a prestigious position as a research assistant to liberal lion Larry Tribe. Chesebro worked in that role alongside future Supreme Court Justice Elena Kagan and a young Jeffrey Toobin, the prominent legal journalist.

I spotted the Tribe connection on Chesebro’s Linkedin profile a few weeks ago. When I reached out to Tribe to inquire about their relationship, Tribe said he had only learned this year that his former mentee had worked for Trump after reading a series of memos published in February by the New York Times.

“I was stunned to see that Ken Chesebro had wound up as part of Team Trump,” Tribe said in a phone interview earlier this month. 

Chesebro is the earliest known example of the Trump campaign considering Jan. 6 as a target for its post-election legal efforts on paper. According to another memo obtained by the Jan. 6 Committee, he laid out in detail what Vice President Mike Pence should do to subvert the election in messages to Rudy Giuliani and Trump legal advisor John Eastman.

According to a second Times story published Wednesday evening, Chesebro told Eastman that “the odds of action before Jan. 6 will become more favorable if the justices start to fear that there will be ‘wild’ chaos on Jan. 6 unless they rule by then, either way.”

The effort to appoint pro-Trump electors is now reportedly being examined by federal prosecutors. 

Chesebro declined to comment to TPM about whether he had been contacted by federal law enforcement in relation to his activities for the Trump campaign, and declined to comment on whether he complied with a subpoena he received from the Jan. 6 Committee in March. 

When asked what kinds of events attorneys could stoke in order to get the attention of the justices after being read the Times “chaos” quote, Chesebro waved off the question, saying that of course any lawyer is concerned about how a case will play in public and with judges. 

“Fortunately or unfortunately, it seems like election integrity is another area where politicians will get involved in the messaging. It’s unfortunate that this is such a focus of attention,” Chesebro said. “Hopefully there will be compromises over the next few years and people won’t have to worry about election integrity.”

When asked why he thought election integrity had become such a high-profile issue, Chesebro told TPM, “I don’t know enough about the field to comment.” 

Contesting the Election

Chesebro told TPM that his work for Trump began with a request from an old friend of his named Jim Troupis, who contacted him on Nov. 10, 2020: Could he help out on the campaign’s litigation in Wisconsin? Troupis, a former Wisconsin judge whose law firm was hired to draw the state’s radical post-2010 gerrymander, was repping Trump in the state.

Chesebro agreed to help with a lawsuit that sought an extraordinary remedy which has now become familiar: disqualifying hundreds of thousands of ballots in the state’s two most Democratic counties.

He sent Troupis a memo laying out the alternate elector scheme for the first time on Nov. 18, per the New York Times. That memo would set the course for the Trump campaign’s post-court approach, which intensified the following month. 

The campaign, Chesebro argued in his memo, did not have to fight for victory by the so-called “safe harbor” date, or by the date when the states certified their electors — Dec. 8, 2020. Jan. 6, 2021 was the real deadline for the Trump campaign, he suggested.

And to get there, the Trump campaign needed to make sure of one thing: that multiple slates of pro-Trump electors in states that the campaign baselessly claimed it had won would be sworn in.

Chesebro’s work for Trump shied away from some of the more outlandish claims that people in Trump’s orbit were latching on to, like Hugo Chavez manipulating the election results from beyond the grave. Instead, he focused on a more staid argument: that election measures taken to run the election in Wisconsin during COVID-19 invalidated Biden’s victory.

It drives at the same result as Sidney Powell and others with more high profile roles were seeking: the election was improperly run, and so Biden’s wins in key states were illegitimate. But it allowed Chesebro to try to bring the patina of elite law to a Trump campaign struggling to find attorneys who would work on its effort to overturn the election result. 

Chesebro’s involvement also brought him back in touch with Eastman, a conservative attorney from the right-wing Claremont Institute who Chesebro worked with on a 2016 Supreme Court amicus brief that described birthright citizenship as a “vestige of feudalism.” Chesebro emphasized to TPM that he had no contact with Eastman from the time of that 2016’s case’s resolution until 2020, when he began to represent Trump, and declined to comment on whether he communicated with Eastman while representing Trump. 

The Cheese

I first reached out to Chesebro earlier this month. We ended up speaking over the phone multiple times and meeting twice in Manhattan, where he recently bought a penthouse apartment. In a Starbucks, in Central Park and on a call as late as Thursday morning, he defended his work for the Trump campaign.

Chesebro would alternately decline to discuss the content of memos released by the New York Times and Jan. 6 Committee, citing legal privilege concerns, point towards general arguments around the principles of legal advocacy, or make broader cultural points about the importance of free and open debate. 

To that last point, Chesebro portrayed his decision to join the Trump campaign’s legal efforts in Wisconsin and then at the Supreme Court to me as partly a reaction to what he saw as something that sounds suspiciously like cancel culture. He was dismayed to see Democrats pressuring companies to drop law firms who agreed to work for the campaign’s post-election efforts. 

“Plaintiffs have difficulty getting the best lawyers to push back against top lawyers who work for corporations,” Chesebro told TPM, a point that he said was impressed on him while in law school by Charlie Nesson, the Harvard Law professor. “And, in a way, it was very similar in November 2020 — the Trump campaign had difficulty getting talent to go up against the Biden team.”

Chesebro has the lawyer’s trait of speaking not in phrases or sentences, but in fleshed out paragraphs —- coupled with a flat, focused intonation that drills at his interlocutor.

When I brought up a particularly controversial moment, or pointed out that many people regard arguments in favor of Trump’s efforts to stay in power as a fundamental breach of the will expressed by American voters in 2020, he took a few tacks: one was to cite somewhat similar arguments made by liberals, like a column by Van Jones and Larry Lessig in favor of submitting alternate elector slates in Pennsylvania in case the state took weeks to count. 

Chesebro is thorough to the point of obsession —- he followed up many arguments he made during interviews by sending me multiple legal briefs and court records from his archives. 

“To the extent that I or any other attorney involved in the 2020 presidential contest, on either side, has come under criticism for identifying possible strategic options that might come into play under various scenarios that could develop, it should be kept in mind that this is what lawyers do,” Chesebro wrote in a supplementary statement he provided to me. “It is the duty of any attorney to leave no stone unturned in examining the legal options that exist in a particular situation.”

It wasn’t only his apparently central importance to how the Trump campaign formulated some of the ideas that led  to Jan. 6 that interested me. It was also that he didn’t appear to fit the profile of a Trump lawyer. 

While Eastman has his Federalist Society and Claremont Institute credentials, Chesebro was a mentee of Tribe. He continued to work with Tribe on liberal cause litigation after graduation, throughout the 1990s. He lacks political experience, but brings many of the standard elite credentials that were missing from nearly all of the Trump 2020 legal team. 

“Ah, The Cheese,” Toobin told me with a chuckle, recalling a law school nickname for Chesebro, a Wisconsin native. 

“The people who worked for Larry were by and large ideologically sympatico with Larry, and his politics were well known,” Toobin remarked, saying he recalled running into Chesebro working in the Harvard Law school library in the years after graduation. “That’s why it’s so surprising to see Ken in this role. I just sort of assumed that he was some kind of a Democrat.” 

At a hearing in the Wisconsin case, the New York Times reported, one justice remarked that the lawsuit had focused on two counties — the “most nonwhite, urban” areas — while seeking to invalidate votes statewide. Another told Troupis that the case “smacks of racism.” 

Chesebro and the team of Trump attorneys ultimately lost that bid to block Biden’s win in the Wisconsin Supreme Court on Dec. 14 in a 4-3 ruling, the end of the line for Chesebro’s efforts to push the alternate elector scheme through the courts.

But another plan was already in place. Five days earlier, the New York Times reported, Chesebro had authored a memo for the Trump campaign laying out the steps that pro-Trump electors in each state that Biden had won would need to take in order to serve as potential alternates on Jan. 6. 

When Dec. 14 and Trump’s loss in the state came around, the electors were ready. Wisconsin’s Republican electors met and cast votes for Trump — per Chesebro’s memo, ready for the state to go back and transmit the Trump, and not Biden, electoral votes to Congress. 

“If you don’t know for sure the final result by December 14, it can be prudent to have multiple electors cast the ballot,” Chesebro told TPM.

“That kind of — as I would call it, Alice in Wonderland or off-the-wall theory shocked me because of its willingness to trash democracy, but not because of its weirdness,” Tribe told me. “Ken would come up with weird ideas from time to time, quite weird ideas, and seem to lack judgment about whether they were sound or not, and didn’t really care about whether they were legitimate.”  

Chesebro maintains that “material deviations from the state statutes’ ‘ in Wisconsin’s 2020 election cast the result into serious doubt. But by that point, courts around the country had thrown out similar arguments. Wisconsin wasn’t going to put Trump ahead. 

By that time, Tribe told me, “it was quite clear that claims Trump really had won the election were quite wild and not to be accepted by courts.” 

The Aftermath

Federal investigators are now reportedly examining the effort to install pro-Trump electors. The Jan. 6 Committee issued Chesebro a subpoena in March, and has obtained at least some of the memos and emails that he wrote for the campaign. 

The arguments were nothing if not creative. One, released in litigation involving Eastman, shows Chesebro telling Rudy Giuliani on Dec. 13 that Pence should recuse himself because he has a “conflict of interest” due to his being on a ticket whose defeat Trump had refused to concede. 

From there, he argued that the president of the Senate, acting in Pence’s place, should assert the right to make judgments about what to do in the case of “conflicting votes” as a way to gain “leverage” for further scrutiny of the election. 

I asked Chesebro about criticism around these moves — weren’t they going beyond the will of the voters? 

“If there is a non-frivolous argument concerning the meaning of the Electoral Count Act or its constitutionality, it’s legitimate to press that and let the courts decide,” Chesebro replied. “We have a system where the courts ultimately resolve these issues, and people can live with how the courts resolve them.”

Chesebro declined to comment on his contacts with Trump himself or members of his inner circle. He told TPM that he had never had any contact with Ginni Thomas, the wife of Supreme Court Justice Clarence Thomas, who is under scrutiny for her activism to push the alternate elector scheme. 

Tribe and Chesebro are no longer close. Tribe said that the most recent substantial contact the two had had was Chesebro offering to get Tribe involved in Bitcoin investments in 2019. 

Before the Bitcoin suggestion, Tribe said, Chesebro had assisted him on Bush v. Gore in 2000. 

Tribe characterized Chesebro as something of a legal nihilist — someone with a penchant for helping “the little guy,” but who remained focused on the “gamesmanship” aspect of the law. 

“I doubt that he cared whether the arguments were sound or not as long as that goal could be met of helping Trump to win the election,” Tribe said. “That’s probably why I wasn’t too surprised to learn that he became very involved with Bitcoin.” 

Given a chance to respond to Tribe’s criticisms, Chesebro told me in a statement, “Lawyers have an ethical obligation to explore every possible argument that might benefit their clients. In my work for the Trump-Pence campaign, I fulfilled that ethical obligation.”

When I mentioned to Chesebro that Tribe had told me about his work on Bush v. Gore, Chesebro jumped on it. 

Chesebro provided TPM with a memo he wrote, dated November 2000, for Gore’s legal team, in which he argued that the Electoral Count Act had the potential to put Al Gore in a tricky position on Jan. 6, 2001: If Gore won the Supreme Court case and, as vice president, presided over the tallying of Florida’s electoral votes, certified by then-Gov. Jeb Bush (R), he would find himself “casting the deciding vote, to break a tie.” 

“This is the kind of wargaming that attorneys do,” Chesebro told TPM, suggesting that his work for the Trump campaign and for Gore sprung from the same well of zeal and curiosity. 

It was a surreal reflection, in Chesebro’s telling, of the Trump campaign’s position pre-Jan. 6, and one that conveniently overlooked the 537-vote margin that Bush won Florida by in 2000, compared to the seven states that Trump was contesting. 

“That’s on the face of it, bullshit,” Tribe told me. “Not to parse words too closely, all of that was well before — all of that was prior to the electoral vote. What Ken is doing in the current situation is trying to unsettle the electoral vote counting process.”

I asked Chesebro what he made of arguments that letting a debate about unsound ideas go on in Congress legitimized them. 

“I understand the concern,” he replied. “But as a lawyer I have to think, the more debate the better, and that usually the side with the better argument will end up winning, at least over the long term.”

Did the side with the better argument win in 2020?

“Not in Wisconsin.”

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