Just before Christmas 2020, as President Donald J. Trump was running out of options to stave off losing the election, Kenneth Chesebro wrote an email to a group of other lawyers who were thinking of filing a last-ditch lawsuit to reverse Mr. Trump’s defeat.
The odds of winning the suit did not look good, Mr. Chesebro wrote, pegging them at only “1 percent.” But even though their efforts were unlikely to prevail in court, Mr. Chesebro suggested that Mr. Trump continue to push his baseless claims of fraud.
“The relevant analysis,” Mr. Chesebro argued, according to emails reviewed by The New York Times, “is political.”
On Friday, Mr. Chesebro pleaded guilty to a single felony count of conspiring to file false documents in Georgia and agreed to cooperate with the local prosecutors who have charged Mr. Trump and 17 others in a sprawling racketeering indictment accusing them of tampering with the election in the state.
Word of his cooperation deal came one day after Sidney Powell, another lawyer who sought to help Mr. Trump remain in power, reached a similar arrangement with the authorities. Last month, an Atlanta bail bondsman with a minor role in the alleged conspiracy also agreed to plead guilty.
“The three folks who’ve pled guilty so far have all apparently avoided jail time and I think that’s an unmistakable signal to other defendants deciding whether or not they want to plead guilty and cooperate,” said Chuck Rosenberg, a former U.S. attorney and senior F.B.I. official.
But Mr. Chesebro’s deal could present a more serious threat to Mr. Trump than the others given that he pleaded guilty to a conspiracy count that involved both the former president and some of his closest allies.
Mr. Chesebro also maintained an extensive correspondence with other pro-Trump lawyers charged in the case and played a central role in one of Mr. Trump’s chief plans to stay in office: a scheme to create slates of pro-Trump electors in states like Georgia, which Mr. Trump had actually lost.
A New York lawyer with an Ivy League pedigree, Mr. Chesebro was the first of several lawyers involved in the so-called fake elector scheme to have decided to turn state’s evidence in either of the two election interference cases Mr. Trump is facing. (While Ms. Powell filed lawsuits making preposterous claims that the election had been rigged against Mr. Trump, she had no direct role in creating fake electors.)
The electors scheme became a vital part of the end game strategy pursued by Mr. Trump as he and his allies sought to find a way to block or delay congressional certification of his Electoral College defeat. When Mr. Trump directed his supporters to march on the Capitol on Jan. 6, 2021, Mr. Chesebro was among them, accompanying the conspiracy theorist Alex Jones to the Capitol grounds. (Mr. Chesebro does not appear to have illegally entered the Capitol as the march turned into a riot.)
If and when Mr. Chesebro takes the stand in Georgia, he could give an insider’s perspective not only on the legal advice he provided to Mr. Trump, but also on another important issue: the roles that other lawyers, including John Eastman and Rudolph W. Giuliani, played in the fake elector scheme.
Moreover, having already put in writing that some of Mr. Trump’s postelection legal maneuvers were feints of a sort undertaken for political ends, Mr. Chesebro might also be able to undermine one of the defenses that the former president could use in both of the election prosecutions.
If Mr. Chesebro were to testify that Mr. Trump’s lawsuits challenging his loss were not designed to win, but merely as ploys to sow doubt about the election, it could cut against Mr. Trump’s possible plan to use a so-called advice of counsel defense. That strategy involves blaming one’s lawyers for giving bad advice.
Beyond his role in the state case in Georgia, Mr. Chesebro was also identified — albeit not by name — as Co-Conspirator 5 in the federal election case filed against Mr. Trump in August by the special counsel, Jack Smith. That indictment described him as a lawyer who helped to craft and implement “a plan to submit fraudulent slates of presidential electors to obstruct the certification process.”
Mr. Smith’s indictment cited several emails — some of which were first made public by The New York Times — showing lawyers working on the fake elector scheme expressing reservations about whether the plan was honest or even legal to begin with. In one of the emails, Mr. Chesebro wrote to Mr. Giuliani that two pro-Trump electors from Arizona were “concerned” that the plan “could appear treasonous.”
Mr. Smith’s indictment also mentioned a memo that Mr. Chesebro wrote in December 2020 as Mr. Trump and his legal team were scrambling for ways to overturn his loss to Joseph R. Biden Jr. In the memo, Mr. Chesebro acknowledged that the fake elector plan was “a bold, controversial strategy” that the Supreme Court was “likely” to reject.
But much like in the email he would send around that Christmas, Mr. Chesebro said the plan had value even if the Supreme Court shot it down. Creating the fake electors would achieve two goals, the memo said. They would focus attention on claims of voter fraud and “buy the Trump campaign more time to win litigation that would deprive Biden of electoral votes and/or add to Trump’s column.”
Steven H. Sadow, the lead lawyer defending Mr. Trump in the Georgia case, said of Mr. Chesebro’s plea deal, “It appears to me that the guilty plea to count 15 of the Fulton County indictment was the result of pressure by Fani Willis and her team and the prosecution’s looming threat of prison time. However, it is very important for everyone to note that the RICO charge and every other count was dismissed.”
Mr. Sadow said, as he had about Ms. Powell’s plea a day earlier, that he expects “truthful testimony” would help his defense strategy.
It remained unclear what effect Mr. Chesebro’s cooperation deal in Georgia might have on Mr. Smith’s federal election case. Like Ms. Powell, Mr. Chesebro has not been charged in Washington and if he were subpoenaed to testify there against Mr. Trump, he could still avoid taking the stand by exercising his Fifth Amendment right against self-incrimination.
Then again, if he did give testimony in Georgia, any statements he made from the stand would be fair game for Mr. Smith’s prosecutors if they ultimately decided to bring charges.
“Cheseboro and Powell are both unindicted co-conspirators in a pending federal indictment. That could make it hard for them to get on the stand in Georgia because truthful answers under oath in that jurisdiction could expose them to criminal liability in the federal case,” said Mr. Rosenberg.
“There is also an open question about how credible they might be — given some of the outlandish claims they made — before a Georgia jury,” he said. “Any good prosecutor would need to weigh the costs and benefits of putting either one of them on the stand.”