When I spoke with Ken Chesebro last year across several interviews, one thing was clear: He saw himself as an elite appellate lawyer and needed recognition.
It came through subtly. Chesebro, who subsequently became known as "Co-Conspirator 5" in Jack Smith's Jan. 6 indictment of Trump, speaks carefully, always emphasizing that he was simply there to support the particular needs of a client.
But as TPM reported last year in an exclusive interview with Chesebro, he started his career on a promising legal track, assisting Harvard Law Professor Lawrence Tribe among a cohort of law students that included future Supreme Court Justice Elena Kagan and journalist Jeffery Toobin.
From there, Chesebro's career drifted from that elite pathway — he notched an early win by serving on a legal team in a case which set a new legal standard for expert testimony, but had faded deep into obscurity by the time 2020 came around. There was a sense of resentment there, as he spoke of what drew him both to legal practice and to representing Trump: "to try to help even the scales in litigation."
Chesebro fought that obscurity in his interviews with TPM, providing reams of paper showing his involvement in appellate litigation over the years, as well as ties to elite figures like Tribe and Barack Obama. That included a reference to a 2016 amicus brief he filed with John Eastman, in which the two argued that birthright citizenship was a "vestige of feudalism."
Chesebro emphasized to TPM that he was the one to have contacted Eastman in that 2016 case — and that he did so not because he agreed with Eastman's theorizing (Chesebro noted that he disagreed with some of Eastman's arguments), but because he lacked the recognition in legal circles which Eastman possessed.
"I knew that he had a good reputation among conservatives and, as far as I could tell, none of the conservative justices knew who I was," Chesebro told TPM.
For Chesebro, that long-sought recognition may finally be arriving — but in the worst way: He is facing the possibility of criminal charges in the alleged conspiracy for which Trump has already been indicted. The New York Times published a Dec. 6, 2020 memo this week written by Chesebro in which he laid out his view for what he saw as Trump's best legal chance at reversing his 2020 loss. Politico wrote in response that Chesebro's work may in fact have been "more instrumental" than that of John Eastman, who was long seen as the mastermind of Trump's legal efforts to remain in power after losing.
The December 2020 memo highlights that Chesebro developed some of the same theories which Eastman would tout weeks later, and which became fundamental to the Stop the Steal legal effort.
Most notably, Chesebro proposed a plan for then-Vice President Mike Pence to try to kick the election to the Supreme Court by refusing to count the votes from states where Chesebro would organize slates of competing fake electors.
That, he argued, would allow the certification joint session on Jan. 6 to be delayed in such a way that "at no point will Trump be behind in the electoral vote count unless and until Biden can obtain a favorable decision from the Supreme Court upholding the Electoral Count Act as constitutional, or otherwise recognizing the power of Congress (and not the president of the Senate) to count the votes."
Three weeks later, on Dec. 23, Eastman circulated his own infamous memo, proposing a broadly similar idea which would have seen Pence declare that the "ongoing disputes" which Chesebro created via the fake electors meant that "there are no electors that can be deemed validly appointed in those States."
Neither Eastman nor Chesebro have been charged with a crime.
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