On Dec. 24, 2020, Kenneth Chesebro and other lawyers fighting to reverse President Donald J. Trump’s election defeat were debating whether to file litigation contesting Joseph R. Biden Jr.’s victory in Wisconsin, a key swing state.
Mr. Chesebro argued there was little doubt that the litigation would fail in court — he put the odds of winning at “1 percent” — as Mr. Trump continued to push his baseless claims of widespread fraud, according to emails reviewed by The New York Times.
But the “relevant analysis,” Mr. Chesebro argued, “is political.”
The emails have new significance because Mr. Chesebro is scheduled to be one of the first two of Mr. Trump’s 18 co-defendants to go on trial this month on charges brought by the district attorney’s office in Fulton County, Ga. The indictment accused Mr. Chesebro of conspiring to create slates of so-called fake electors pledged to Mr. Trump in several states that Mr. Biden had won.
Mr. Chesebro’s lawyers have argued that his work was shielded by the First Amendment and that he “acted within his capacity as a lawyer.” They have called for his case to be dismissed, saying he was merely “researching and finding precedents in order to form a legal opinion, which was then supplied to his client, the Trump campaign.”
Scott R. Grubman, a lawyer for Mr. Chesebro, said lawyers often argue for positions that are not widely held. “For example, any lawyer who has ever filed a pleading challenging existing Supreme Court precedent falls within this category,” he said. “Maybe a long shot, but far from criminal. In fact, it’s how the law changes over time.”
Mr. Trump has also signaled that one of his possible defenses is that he was simply acting on the advice of his lawyers.
But Mr. Chesebro’s emails could undercut any effort to show that the lawyers were focused solely on legal strategies. Rather than considering just the law and the facts of the case, Mr. Chesebro made clear he was considering politics and was well aware of how the Trump campaign’s legal filings could be used as ammunition for Republicans’ efforts to overturn the results when Congress met to certify the Electoral College outcome on Jan. 6, 2021.
“Just getting this on file means that on Jan. 6, the court will either have ruled on the merits or, vastly more likely, will have appeared to dodge again,” Mr. Chesebro wrote in the email chain. He added that a lack of action by the Supreme Court would feed “the impression that the courts lacked the courage to fairly and timely consider these complaints, and justifying a political argument on Jan. 6 that none of the electoral votes from the states with regard to which the judicial process has failed should be counted.”
Of the chances of success, Mr. Chesebro estimated the “odds the court would grant effective relief before Jan. 6, I’d say only 1 percent.” But he wrote the filing has “possible political value.”
Mr. Chesebro wrote that it was “hard to have enormous optimism about what will happen on Jan. 6, but a lot can happen in the 13 days left until then, and I think having as many states under review both judicially and in state legislatures as possible is ideal.”
He said the legal filings could produce a “political payoff” to bolster the argument that “there should at least be extended debate in Congress about election irregularities in each state.” He added that “the public should come away from this believing that the election in Wisconsin was likely rigged, and stolen by Biden and Harris, who were not legitimately elected.”
Responding to the email chain was John Eastman, the conservative lawyer who has also been charged in the Georgia election case. Mr. Eastman said he believed the legal arguments were “rock solid” but the odds of success were “not based on the legal merits, but an assessment of the justices’ spines. And I understand that there is a heated fight underway.”
Mr. Chesebro responded: “I particularly agree that getting this on file gives more ammo to the justices fighting for the court to intervene. I think the odds of action before Jan. 6 will become more favorable if the justices start to fear that there will be ‘wild’ chaos on Jan. 6 unless they rule by then, either way.”
Mr. Trump had posted to Twitter days before for his followers to come to the Capitol on Jan. 6, telling them to “be there. Will be Wild.” Thousands of his supporters stormed the building, injuring at least 150 officers and delaying an official proceeding of Congress.
Mr. Chesebro and Sidney Powell, another Trump lawyer, are the only ones to seek speedy trials, as Georgia allows. Jury selection is scheduled to begin on Monday.
Photographs and videos reviewed by The New York Times suggest that Mr. Chesebro, a quiet Harvard Law graduate from Wisconsin, was in the crowd outside the Capitol on Jan. 6, 2021. He had spent part of that day closely following the conspiracy theorist Alex Jones, who helped lead a mob toward the building.