Since then, Chesebro has kept a low profile. He decamped to Puerto Rico from New York last year, and some friends said he’d fallen out of touch. A prominent law firm issued no public announcement last year when it tapped him to run a new department and added no mention of him to its website.
Lawyers handling a case against him in Wisconsin have told a judge they were unable to locate him. Even the House select committee that investigated the pro-Trump attack on the Capitol did not depose him until last fall, after it had interviewed more than a thousand others and conducted public hearings, because it had trouble finding him, according to a person familiar with the situation who was not authorized to speak publicly.
A Harvard-trained lawyer once keen on liberal causes, and registered as a Democrat as recently as 2016, Chesebro may be the least well known of the small set of figures key to both indictments. His retreat from public life since Jan. 6 has deepened the mystery for former classmates and colleagues puzzling over how he became a central player in plans to reverse the outcome of a democratic election.
“The Ken I knew would not have been involved with that,” said Holly Hostrop, a lawyer who worked with Chesebro about 20 years ago on litigation against the tobacco industry that extracted millions in punitive damages for ailing smokers. “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 attorney did not respond to requests for comment. As part of a rare interview with Talking Points Memo last summer, Chesebro issued a statement saying, “It is the duty of any attorney to leave no stone unturned in examining the legal options that exist in a particular situation.”
The successful appellate lawyer studied at Harvard University under Laurence Tribe, the preeminent legal scholar who advised congressional Democrats on both of Trump’s impeachments. Chesebro continued working with Tribe for about 20 years, on wide-ranging litigation involving class-action claims and punitive damages.
But friends said his politics seemed to shift after he reaped sizable returns from his investments in cryptocurrency in the past half-decade. He began to stake out more-libertarian positions in legal briefs, especially in his home state of Wisconsin, where he started donating to Republicans and working with a former judge, Jim Troupis, who Chesebro would later testify under oath had brought him into Trump’s orbit.
“He was not making good-faith legal arguments for his client,” said Tribe, who said he has been distressed to see his former mentee emerge as an architect of Trump’s plans to cling to power. “He was inventing legal fiction that paid no attention to the law and creating a pretext for a conspiracy to steal an election.”
Chesebro (pronounced “Chez-bro,” after the family’s origins in an English borough on the River Chess) was raised in Wisconsin Rapids, about 100 miles north of Madison, according to a relative who spoke on the condition of anonymity to share private details. His father was a music teacher, his mother a speech therapist.
After attending Northwestern University, Chesebro went on to Harvard Law School, where some classmates knew him as “The Cheese.” He graduated in 1986, the same year as Elena Kagan, the Supreme Court justice, and a year ahead of Ron Klain, Biden’s longtime aide and former White House chief of staff — all were research assistants for Tribe, the professor said.
A brief detour to Washington involved a clerkship with Gerhard A. Gesell, a federal judge whose prominent cases included Watergate trials in which he affirmed that “it is impossible to preserve freedom anywhere when the zealots take over and the rule of law is ignored.” Then Chesebro returned to Cambridge, Mass., to continue working with Tribe.
Chesebro’s relationship with the influential professor was unique, former classmates said. “He idolized Larry Tribe,” said Jonathan Massey, a prominent Washington lawyer, who recalled that Chesebro, “a pretty standard liberal,” was among the first to turn the traditional role of student research assistant into a post-law-school career.
When Tribe invited him to a fundraiser for Barack Obama’s Senate campaign in 2004, Chesebro responded with effusive praise for the rising Democratic star, also a former Tribe research assistant. He wrote that the candidate’s speech at that year’s Democratic National Convention recalled the oratory of Abraham Lincoln, according to emails first reported by the newsletter Air Mail and reviewed by The Washington Post. And he mused that Obama would “make a pretty good Supreme Court justice.”
In 2014, Chesebro invested in a bitcoin fund overseen by Grayscale, a cryptocurrency asset manager, he would later write to Tribe. He said he invested a “low six-figure sum” and ended up making “several million dollars” when he sold in 2017. Then, after prices crashed in 2018, he reinvested his profits, he wrote.
Chesebro began working for the Trump campaign about six days after the 2020 election, at the request of Troupis, he would later tell the House select committee investigating the Jan. 6 attack. Troupis “wanted help from an appellate lawyer going forward to make sure that he could adequately staff the case,” Chesebro said.
A Nov. 18, 2020, memo from Chesebro urged Trump electors to meet and vote in Wisconsin because of the ongoing recount in that state, according to the indictment. Then, Chesebro wrote in a Dec. 6 memo that Trump electors should convene not just in Wisconsin but in six “contested States” as a way to “prevent Biden from amassing 270 electoral votes.” The memo anticipated that Pence would not just open but count the sham votes, creating uncertainty about the election’s true victor. In a memo three days later, federal prosecutors charge, Chesebro provided “instructions on how fraudulent electors could mimic legitimate electors.”
On Dec. 13, the day before the electors were to convene, Chesebro emailed Trump lawyer Rudy Giuliani to argue that Pence could choose from among “conflicting votes” presented to Congress, according to documents released by House investigators and cited in the Georgia indictment. The suggestion was at odds with how mainstream lawyers have long interpreted the U.S. Constitution’s 12th Amendment and the Electoral Count Act of 1887. But Chesebro wrote that his proposal “seems preferable to allowing the Electoral Count Act to operate by its terms,” according to the indictment.
The committee also asked Chesebro in his deposition about documents showing he was on a list to attend a Dec. 16 meeting at the White House. He declined to answer, as he did with many of the committee’s questions, invoking attorney-client privilege and the Fifth Amendment’s protection against self-incrimination.
On Christmas Eve, as he and Eastman sized up the chances that four Supreme Court justices — the number needed to take a case — would agree to hear an election-related complaint, Chesebro wrote in an email cited by the House committee that the justices might be moved to act if they feared “chaos” on Jan. 6.
In May 2022, two Biden electors and another Democrat in Wisconsin sued Chesebro, along with Troupis and the state’s 10 fake electors, arguing that they took part in a “civil conspiracy,” unlawfully assumed a public office and caused a public nuisance, in violation of state and federal laws.
Chesebro was initially served in the case at an apartment on Central Park in New York, according to a June 2022 filing in the case. But lawyers complained that he became difficult to locate after that, according to subsequent filings. A doorman at the plush New York apartment soon said he no longer lived there, one filing said.
In October, Napoli Shkolnik, a New York-based personal injury firm whose high-profile clients have included victims of the Sept. 11 attacks and residents of Flint, Mich., affected by the water crisis there, informed employees in an email that it had brought on Chesebro for an important role. Gloria Werle, the firm’s chief operating officer, wrote that Chesebro was “heading up our new Law & Motions Department” and that he and his wife were relocating to Puerto Rico, where some of the partners live. Chesebro’s work, according to the email, would include drafting “some of the firm’s most important filings.”
Chesebro’s affiliation with Napoli Shkolnik has come up in two recent lawsuits against the firm, filed by former employees alleging discrimination, harassment and retaliation — and arguing that his hiring showed the firm did not value ethics and inclusivity. The firm has denied the allegations and moved to dismiss the lawsuits.
In an interview before Monday’s indictment, Napoli said Chesebro “advised us that he had some relationship with Jan. 6, but we didn’t really realize what it was. He sort of downplayed it.” Because he is now a “lightning rod for opinions,” Chesebro would probably receive less work from the firm, Napoli predicted.
About 10 days after his affiliation with the Napoli firm was announced internally, a group called Lawyers Defending American Democracy filed an ethics complaint against him in New York, asking a state grievance committee to investigate his conduct and “impose appropriate sanctions.” Tribe was among dozens of high-profile legal figures who signed the complaint.
This content was originally published here.