politics

The blinds were drawn at a handsome villa in an oceanfront gated community on the northern coast of this Caribbean island. Inside, a woman’s voice could be heard calling out “Ken” — but no one answered the door.

Records show this is the tropical refuge of Kenneth J. Chesebro, a lawyer who allegedly marshaled supporters of President Donald Trump to pose as electors in states won by Joe Biden in 2020, creating a pretext for Vice President Mike Pence to delay counting or disregard valid electoral college votes on Jan. 6, 2021.

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.

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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.”

“This is what lawyers do,” he added. 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.