The Strange Life of Trump Attorney Kenneth Chesebro

Official portrait of President Donald J. Trump, Friday, October 6, 2017. Official White House photo by Shealah Craighead. Photo is in the Public Domain.

He’s a man with Wisconsin roots and that, along with his last name, led his fellow students at Harvard Law School to dub Kenneth Chesebro “the cheese” — though his name is actually pronounced “Chez-bro.” The attorney has now become a big cheese in the cases against Donald Trump for trying to overturn the 2020 election of Democrat Joe Biden.

Chesebro has been named as Co-Conspirator 5 in the federal indictment against Trump and tied for fifth (with seven charges against him) among the 18 co-conspirators charged yesterday by the Fulton County District Attorney in Georgia. Chesebro was the “key architect” of a strategy to use fake electors to overturn the election which is “the cornerstone” of the federal indictment against Trump. as the New York Times has reported.

And Chesebro connected to two other Wisconsinites with the scheme: He first proposed the idea in a Nov. 18 memo to Jim Troupis, a former Wisconsin judge and longtime Republican operative in this state who worked as a Trump attorney. And Chesebro also met with Brian Schimming, who’s now chairman of the Republican Party of Wisconsin, to discuss this scheme, accruing to the Fulton County indictment.

The story of his college nickname was included in a fascinating profile of Chesebro written by legal analyst Jeffrey Toobin for the online publication Air Mail. Toobin attended Harvard at the same time as Chesebro, and describe him as “a shy, awkward nerd among nerds.”

“Chesebro was born in 1961 and grew up in a small town in central Wisconsin, where his father was a public-school music teacher,’ the story notes. “Ken was a competitive debater in high school and college, at Northwestern, and when he arrived in Cambridge for law school, in 1983, he looked much as he does now: the same shock of brown hair flopping onto his forehead, the same aversion to eye contact.”

Both Chesebro and Toobin were mentored by liberal Harvard law professor Lawrence Tribe, though Tribe considered some of Chesebro’s legal theories “too for out.”

In those days and for decades after Chesebro was a Democrat. After graduation, in 1986, he moved to Washington to work for District Judge Gerhard Gesell, who would soon become famous for presiding over the trial of Oliver North. Chesebro’s LinkedIn profile lists him serving as Deputy Special Counsel, Office of the Independent Counsel for Iran/Contra Matters for the U.S. Department of Justice. 

But Chesebro soon moved back to Cambridge where he set up a practice as a solo practitioner, an unusual career move, where he often did work for Tribe. “He maintained an enduring, puppyish devotion to Tribe, who still, on occasion, hired him to help with his cases,” the story reports. But mostly Chesebro did brief-writing for plaintiffs in civil litigation, often in personal-injury cases or class actions. His LinkedIn profile says “Kenneth Chesebro has handled more than 100 cases in the U.S. Supreme Court and lower courts, frequently on behalf of trial lawyers pursuing high-profile litigation against corporations.” Typically he represented Democratic plaintiffs. In 1993 Chesebro wrote a long article in the American University Law Review defending work for such plaintiffs and skewering “Reagan Administration ideologues and their colleagues in Congress.”

“Chesebro’s political contributions in those days went only to Democrats, including $1,000 to Senator Russ Feingold, …$1,000 to the Clinton-Gore ticket in 1996; and $1,000 to Senator John Kerry in 2000…He assisted Tribe in his representation of Al Gore in the Supreme Court after the 2000 election. In a dense memo, dated November 27, 2000, to another member of the Gore legal team, Chesebro strategized about how Gore might prevail when the electoral votes were counted, on January 6, 2001,” the story recounts.

But in his 50s, Chesebro went through a stunning mid-life crisis after investing in Bitcoin, selling out four years later and making a fortune. It was around this time that Chesebro transformed his life, splitting with his wife of more than two decades and buying a penthouse apartment at 230 Central Park South in Manhattan, where an adjacent penthouse “is currently on the market for $13.95 million… Around his 60th birthday, Chesebro began courting a young woman, providing trips around the world, including an extended one to Paris and London to celebrate her 21st birthday. According to (a) family friend, the couple has since married,” the story notes.

Meanwhile the cheese had turned Republican, making political donations to GOP candidates. In 2020, he gave $2,800 to Trump’s presidential campaign and $2,800 to Senator J. D. Vance, in Ohio. Over two elections he gave $5,800 to Ron Johnson, the Republican who defeated Feingold, the man Chesebro was still supporting (in an email to Tribe) as recently as 2004. In all, Chesebro has given more than $50,000 to various Republican politicians in recent years.

Chesebro had also switched to representing Republicans in court. He represented Senators Ted Cruz, Mike Lee and other Republican politicians in an amicus brief to the Supreme Court on a voting-rights case out of Utah. His co-author on that brief was Troupis.

“Chesebro became entwined in the Trump effort when Troupis reached out to him,” Toobin writes. “In his deposition before the congressional January 6 investigating committee, Chesebro testified that Troupis—the ‘lead attorney for Trump in Wisconsin’—called him on November 9, which was six days after Election Day and two days after the national race was called for Biden.”  Working pro bono for Trump and “exercising the kind of legal creativity that had been his trademark since law school,” it was Chesebro “who came up with the fake elector scheme.”

Chesebro’s style of argumentation was described by Josh Kovensky, who interviewed the attorney in a June 2022 story for Talking Points Memo: “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… 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.”

Chesebro cited writings by his former mentor Lawrence Tribe in his memos outlining his fake electors strategy. As those memos were exposed in legal filings, Tribe reacted by writing an essay declaring that Chesebro “relied on a gross misrepresentation of my scholarship.”

Back in October, as Cheseboro’s role in the attempted election overthrow began to become clear Tribe told the Times that “he attended Mr. Chesebro’s wedding and once considered him a friend, but then gradually came to see him as an ‘ideological chameleon’ who had adopted ‘the posture he thought would appeal to me’ and ‘came to distrust Ken’s sense of boundaries and his moral compass.'”

Chesebro himself apparently had some qualms about his scheme: he wrote a December 11 e-mail to Rudolph Giuliani and others on the legal team expressing the fear that the fake elector plan “could appear treasonous,” according to the federal indictment. That might just make him of special interest to Fulton County prosecutor Fani Willis, who will likely be looking to flip some of the defendants indicted with Trump.

Legal analyst Mark Herrmann has predicted that the cheese is ripe to turn on Trump. “I smell something funny about Chesebro,” he writes. “Perhaps Chesebro will make a deal with federal prosecutors before the other unindicted co-conspirators. Perhaps Chesebro’s defense will take a different route.”

If Chesebro’s past proves anything, it’s that he’s very capable of flipping his legal and political views.