For Kenneth Chesebro, political turnabout ends in guilty plea

Attorney reaches 11th hour plea deal with prosecutors

One of the lead architects of Republican efforts to reverse Joe Biden’s presidential election victory in Georgia and other states was once a registered Democrat who supported liberal causes before he started working for Donald Trump’s campaign.

Aside from puzzling his former colleagues and drawing scorn from his Harvard Law School mentor, Kenneth Chesebro’s political transformation and the decisions he made afterward culminated Friday in a guilty plea to a felony.

Chesebro, pronounced “Chez-bro,” had been facing seven felony racketeering and conspiracy counts in the wide-ranging indictment brought against him, Trump and 17 others in Fulton County. State prosecutors accused him of helping coordinate slates of Trump electors in Georgia and other states despite the former Republican president’s loss in the 2020 election.

Chesebro was working out the final details of his plea to a single count of conspiracy to commit filing false documents even as about 450 Fulton residents were filling out juror questionnaires on another floor of the courthouse. He had been scheduled to stand trial with fellow attorney, Sidney Powell. But Powell reached a plea deal on Thursday which — like Chesebro’s — allows her to avoid jail time if she cooperates with prosecutors. An attorney for Chesebro said Friday he would likely be able to continue practicing law under his plea deal.

It’s a stunning turnabout for the “nerdy” and “driven” Ivy League lawyer who reportedly made millions of dollars investing in cryptocurrency.

In a separate election interference case pending in a federal court in Washington, Chesebro is not charged but is identified as “Co-Conspirator 5.” The federal indictment says a series of legal memos he wrote for the Trump campaign evolved over time into “a corrupt plan to subvert the federal government function by stopping Biden electors’ votes from being counted and certified.”

“The Ken I knew would not have been involved with that,” Holly Hostrop, a lawyer who worked with Chesebro on behalf of ailing smokers in litigation against the tobacco industry many years ago, told The Washington Post. “I have great respect for his legal skills and felt we were on the side of angels in that litigation. It makes me wonder how he got sucked into this.”

Chesebro and his attorneys had maintained he was simply offering the Trump campaign legal options and that his prosecution effectively criminalizes aggressive lawyering.

‘The Cheese’

The son of a music teacher and a speech therapist, Kenneth John Chesebro, 62, grew up in Wisconsin. His late father, Donald Chesebro, was a U.S. Army veteran who taught in the Wisconsin Rapids Public Schools system and performed with the Don Chesebro Band, according to his 2010 obituary published in the Stevens Point Journal.

The obituary says Chesebro’s father had one other son and two daughters and was inducted into “the Polka Hall of Fame. Don was widely regarded as one of the best clarinet players in the state of Wisconsin.”

Kenneth Chesebro joined the intercollegiate debate team and studied communication, economics and politics at Northwestern University, where he graduated in 1983, according to his LinkedIn profile. Next, he headed to Harvard Law School, where he was dubbed “The Cheese.” The nickname was ironic, said Harvard law classmate Jeffrey Toobin, a legal analyst and journalist who described Chesebro as a “retiring” and “nerdy” and who had “this way of not looking you in the eye.”

“He always had a bit of a weakness for the argument that was a little too clever and too out there. And maybe that is what he was doing on Trump’s behalf,” Toobin told The Atlanta Journal-Constitution.

Marc Mayerson, another Harvard law classmate, remembers Chesebro as an “overeager participant on highly technical issues. And that seems to be the man we have today as well.”

“Ken was extremely driven, a climber, essentially,” Mayerson, an attorney based in Washington, D.C., said in an interview with The AJC.

Along with Mayerson and Toobin, Chesebro graduated from Harvard in 1986. Among their classmates was Elena Kagan, now a U.S. Supreme Court justice. Ron Klain, Biden’s former White House chief of staff, graduated a year behind them.

Like Klain, Kagan and Toobin, Chesebro worked as a research assistant to Laurence Tribe, a prominent Harvard law professor and liberal legal scholar. Chesebro worked alongside Barack Obama, doing research for a Harvard Law Review article by Tribe, according to an extensive profile Toobin wrote about his former Harvard classmate for Air Mail. In 2000, Chesebro helped Tribe represent then-Vice President Al Gore before the U.S. Supreme Court concerning his presidential election defeat to George W. Bush.

“What stood out to me was this incredible devotion to Larry Tribe that was almost like an obsession. I don’t know if Larry thought of him as a protégé, but he certainly thought of himself as a protégé,” Toobin said. “A bunch of us worked for Larry during law school, but then we sort of went our separate ways. What was unusual about Ken is that he remained so close to Larry, which makes this political transformation so astonishing.”

Chesebro has since drawn sharp criticism from his former mentor. In an article published by Just Security on Aug. 8, Tribe called Chesebro’s Trump electors scheme a “fraud” that “relied on a gross misrepresentation of my scholarship.”

In October of last year, Tribe signed onto an ethics complaint Lawyers Defending American Democracy filed against Chesebro with the New York Supreme Court’s Attorney Grievance Committee. Signed by dozens of other attorneys, legal scholars and former prosecutors, the complaint says the “lies that [Chesebro] and his confreres perpetrated have undermined public faith in our elections and caused incalculable damage to our democratic values and institutions.” It also asks the committee to investigate Chesebro and “impose appropriate sanctions.”

That complaint, along with another one from the 65 Project, a pro-democracy group, are pending.

Chesebro’s lawyers had cast their client as a constitutional law scholar who was simply providing legal advice. But his involvement in Trump’s post-election activities went deeper than that. Citing videos and photos, CNN reported in August that Chesebro, wearing a red Trump 2020 hat, followed conspiracy theorist Alex Jones to the U.S. Capitol grounds during the Jan. 6 insurrection. There was no indication, CNN added, that Chesebro entered the Capitol Building or was violent. Fulton County prosecutors intended to call Jones and others to testify in their case against Chesebro before he reached his plea deal.

Chesebro did not respond to requests for comment for this article. But he laid out his defense in an interview last year with Talking Points Memo.

“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 said. “It is the duty of any attorney to leave no stone unturned in examining the legal options that exist in a particular situation.”

Bitcoin bonanza

After he graduated from Harvard, Chesebro clerked for Gerhard Gesell, an outspoken and liberal federal judge who was appointed by President Lyndon Johnson and who presided over the trials for the suspects in the Watergate investigation during Richard Nixon’s presidency. In 1993, Chesebro worked as a deputy special counsel for the U.S. Justice Department in the investigation of the Reagan administration’s Iran-Contra scandal.

Chesebro moved into private practice, often helping plaintiffs’ attorneys in lawsuits against corporations. He supported ailing Vietnam War veterans and smokers in their legal battles with Agent Orange manufacturers and the tobacco industry.

Meanwhile, he donated to left-leaning politicians. Between 1992 and 2000, Chesebro contributed more than $5,000 to Democrats, including President Bill Clinton and U.S. Sen. John Kerry, according to Open Secrets, a nonpartisan group which tracks political spending. But since 2014, he has donated more than $47,000 to Republicans, including Trump and then-U.S. Rep. Devin Nunes.

In 2016, Chesebro changed his party registration in Massachusetts from Democrat to “unenrolled,” according to Cambridge city officials, meaning he was still eligible to vote but as an independent. That same year, he joined conservative legal causes, teaming up with the Wisconsin Institute for Law and Liberty, a right-leaning legal and research organization, and John Eastman, a senior fellow with the Claremont Institute, a conservative think tank. Eastman has also been charged in the Fulton case.

Booking shot of Kenneth Chesebro at the Fulton County Jail on Aug. 23, 2023. (Fulton County Sheriff's Office)

Credit: Fulton County Sheriff's Office

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Credit: Fulton County Sheriff's Office

In 2018, Chesebro joined James Troupis, a former Wisconsin circuit court judge, in representing Republican U.S. Sens. Mike Lee of Utah and Ted Cruz of Texas in a case focusing on Utah’s election system.

Troupis was Chesebro’s connection to Trump, court records show. In October of 2022, Chesebro told a congressional committee investigating the Jan. 6 insurrection that Troupis reached out to him about helping the Trump campaign with a vote recount in Wisconsin after Trump had lost that state in the 2020 election.

Around the time Chesebro began working with Troupis, he boasted to Tribe of a multimillion-dollar profit from investing in cryptocurrency and he tried to convince his former mentor to invest the same way, Toobin said. Tribe told him he wasn’t interested, according to Toobin, who has been scratching his head over his former Harvard classmate’s political about-face.

“The whole thing is so bizarre,” Toobin said. “What makes the story interesting is that it is just kind of a mystery. What happened to this guy?”

AJC staff writer Tamar Hallerman contributed to this report.