Kenneth Chesebro is a formerly liberal, Harvard-educated attorney who was the architect of the fake electors scheme to prevent congressional certification of President Biden’s electoral victory. Although he flew under the radar for more than a year after the insurrection, he was deeply involved in coordinating Trump’s multi-pronged attempts to overturn the results of the 2020 election.
In August 2023, Chesebro was indicted along with the ex-president in Fulton County, Georgia’s sweeping RICO case against 19 co-defendants. He is also cited 13 times as co-conspirator #5 in the Department of Justice’s federal election interference indictment of Trump, but has not been charged in that case.
Just prior to going to trial in October, Chesebro struck a plea deal with Georgia prosecutors, becoming the second Trump lawyer to agree to testify against him if asked to do so. Although he was originally charged with seven felonies — including one under that state’s racketeering law — he was allowed to plead guilty to a single felony charge of conspiracy in exchange for his ongoing cooperation. He also exchanged the prospect of going to jail for a sentence of five years’ probation, and will likely retain his license to practice law.
As a lawyer, 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. He is also an “appellate generalist” (according to his LinkedIn profile) who has covered a wide range of other appellate matters over his almost 40-year legal career, frequently involving constitutional law issues. Chesebro has twice represented members of Congress on constitutional matters in the U.S. Supreme Court; represented the attorneys general of 21 states in defending the right of Vietnam veterans to sue the chemical companies that manufactured Agent Orange; served as Deputy Special Counsel in the Iran/Contra investigation; and assisted with workshops at the Federal Judicial Center to help guide federal judges on expert testimony.
A native of Wisconsin, Chesebro was dubbed “the Cheese” during his college years. He earned a B.S. at Northwestern University in 1983 and a J.D. at Harvard Law School in 1986. There he served as an editor of the Harvard Law Review and landed a position as a research assistant to liberal law professor Larry Tribe, where he worked alongside future Supreme Court Justice Elena Kagan; Biden’s future Chief of Staff Ron Klain; and well-known legal analyst and journalist Jeffrey Toobin, who published a profile of him titled “Legal Weasel” just after his indictment in August 2023.
In the piece, Toobin quotes Tribe (his and Chesebro’s mentor) as saying, “I’m somewhat adventuresome in the way I connect things. But Ken would often go too far out for me. There was a lack of judgment.”
Prior to helping Trump, Chesebro had one other experience working on a controversial presidential election — assisting Tribe in the Bush v. Gore Supreme Court case in 2000.
A longtime Democrat, Chesebro had a political about-face in 2016 after making windfall profits from his crypto currency investments in the preceding years. He donated to the Republican senatorial campaigns of Ron Johnson and J.D. Vance, and in 2020 gave the maximum contribution allowed ($2,800) to Trump.
Tribe is now among the prominent lawyers calling for Chesebro to be disbarred in New York. “Ken grossly misrepresented my work in 2000 and everything I believe,” he told Toobin. “And he was trying to do the opposite [for Trump] of what we were trying to do [for Gore]. We were trying to get recounts to identify the will of the voters. What Ken was doing was trying to overrule the will of the voters. It’s important not to penalize people for making creative legal arguments, but it’s another thing to make up legal arguments that have no legal basis…. Even though we used to be friends, I really think he should never again be allowed to practice law.”
January 6, 2021
- Working pro bono, Chesebro sent the first of three legal memos to James Troupis, Trump’s lead attorney in Wisconsin, on Nov. 18, 2020, with follow-ups on Dec. 6 and Dec. 9. Troupis had initially phoned him for advice on Nov. 9, two days after the race was called for Biden.
- On Dec. 9, 2020, Chesebro sent a five-page legal memo to the Trump campaign outlining the steps pro-Trump electors in each state that Biden had won would need to take in order to serve as potential alternate electors on Jan. 6.
- On Dec. 13, 2020, Chesebro sent a confidential memo to Trump’s lawyer Rudy Giuliani explaining the role Vice President Mike Pence could play in challenging the Electoral College count on Jan. 6 to prevent the certification of Biden as president. Even if the effort failed to keep Trump in office for a second term, Chesebro wrote, “much will still have been accomplished in riveting public attention on election abuses, and building momentum to prevent similar abuses in the future.”
- On Dec. 24, 2020, Chesebro exchanged emails with other members of Trump’s legal team debating whether to file litigation contesting Biden’s victory in Wisconsin, one of the key swing states the Trump campaign still hoped to win somehow. Although he admitted the odds of prevailing in such a case were “1 percent,” he argued that the “relevant analysis is political,” according to emails reviewed by The New York Times. “Just getting this on file means that on Jan. 6, the court will either have ruled on the merits or, vastly more likely, will have appeared to dodge again,” he wrote in the email chain. If the Supreme Court failed to act, he added, it would feed “the impression that the courts lacked the courage to fairly and timely consider these complaints, and [justify] a political argument on Jan. 6 that none of the electoral votes from the states with regard to which the judicial process has failed should be counted.”
- Echoing Trump’s tweet to his followers on Dec. 19 to “be there” on Jan. 6, which he predicted “will be wild!,” Chesebro responded to an email from attorney John Eastman by writing: “I particularly agree that getting this on file gives more ammo to the justices fighting for the court to intervene. I think 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.”
- Chesebro appears in photographs and videos of the crowd outside the Capitol on Jan. 6, according to The New York Times. He had reportedly spent the day in D.C. shadowing conspiracy theorist Alex Jones, who ultimately helped lead a mob toward the building. It’s unclear whether or not Chesebro actually entered the Capitol that day.
- On March 1, 2022, the House Select Committee investigating the attack on the Capitol subpoenaed Chesebro. He initially fought the subpoena but finally testified on Oct. 26.
- In June 2022, Chesebro told TPM that the insurrection 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.”
- As the Aug. 1, 2023, DOJ indictment indicates, starting on Dec. 6, 2020, Chesebro wrote memos recommending that Trump’s electors “in six purportedly contested states (Arizona, Georgia, Michigan, Nevada, Pennsylvania, and Wisconsin) should meet and mimic as best as possible the actions of the legitimate Biden electors, and that on January 6, the Vice President should open and count the fraudulent votes, setting up a fake controversy that would derail the proper certification of Biden as president-elect.”