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.