Pro-Trump lawyers central to alternate-elector plot settle Wisconsin lawsuit

Two attorneys who advanced a strategy to try to overturn the 2020 presidential election by organizing rosters of Republicans to falsely portray Donald Trump as the winner of several states have reached a legal settlement in Wisconsin with two of the state’s rightful electors and a Democratic voter, ending a lawsuit.

As part of the settlement, the two lawyers - James Troupis, a former Dane County judge who oversaw Trump’s legal efforts in Wisconsin, and Kenneth Chesebro, an architect of the plan to try to invalidate Joe Biden’s win by convening Republican electors in seven states - released a trove of their communications Monday about their work after the 2020 election. The attorneys also agreed to not facilitate or send documents on behalf of future presidential electors who are not certified as true electors - unless there is explicit language that the electoral votes would be counted if legal challenges resulted in changes to electoral outcomes.

Troupis and Chesebro did not admit to liability or culpability for their roles in the elector strategy, records show. Troupis agreed to pay an undisclosed financial settlement to the plaintiffs.

Troupis and Chesebro did not immediately respond to requests for comment.

The agreement comes on the heels of another legal settlement in Wisconsin by the same plaintiffs with the 10 Republicans who falsely purported Trump as their state’s winner. In December, they agreed to withdraw their inaccurate filings, acknowledge that Biden won the presidency, and not serve as presidential electors in 2024 or in any election where Trump is on the ballot. That civil settlement marked the first time pro-Trump electors had agreed to revoke their untrue filings and not repeat their actions in the 2024 presidential election.

The cache of records from Troupis and Chesebro reveal additional details about the heavy involvement of both men in the alternate-elector strategy as they sought to give Vice President Mike Pence a reason to declare that the outcome of the election was somehow in doubt on Jan. 6, 2021, when he presided over the congressional counting of the electoral college votes.

The text messages, emails and other records released Monday show how Troupis helped give Chesebro’s legal theories a vital audience: Trump’s allies, who helped bring them to fruition. The records trace the evolution of a kernel of a legal theory that began in Wisconsin in the days after Trump’s defeat and rapidly grew into what prosecutors have called a multistate conspiracy to prevent Biden from taking office.

While Troupis’s early involvement in the operation was known, the extent of his role and volume of his communications with those in Trump’s orbit has been less understood. Troupis’s contributions to the elector plan were largely overshadowed by the attention paid to the work performed by two chief architects of the elector strategy, Chesebro and California attorney John Eastman. Both men’s roles have faced significant scrutiny.

“By publishing these documents and restricting the defendants from submitting fake votes again we are providing Wisconsinites with the transparency and accountability they deserve,” said Scott Thompson, an attorney with the liberal nonprofit firm Law Forward that represented the Biden electors. “Today is a win for our democracy.”

The documents could help investigators and prosecutors across the country. Republicans in five states that Biden won - Arizona, Georgia, Michigan, Nevada and Wisconsin - filled out paperwork in December 2020 claiming Trump had won. Republicans in Pennsylvania and New Mexico also filled out elector paperwork; theirs included caveats that said their votes were to be counted only if they prevailed in litigation over the 2020 election outcome. Trump’s supporters used the material to try to prevent Congress from certifying Biden’s victory. Congress confirmed Biden had won on Jan. 6, 2021, hours after a pro-Trump mob stormed the U.S. Capitol.

Special counsel Jack Smith has been investigating the attempt to overturn the 2020 results for the Department of Justice, and last year a federal grand jury indicted Trump for his alleged involvement. Meanwhile, prosecutors in Michigan, Georgia and Nevada have obtained felony charges against some Republican electors. An investigation by Arizona’s attorney general into the GOP electors is ongoing. The records shed new light on how the plan was assembled there. The settlement agreement indicates that Chesebro gave the documents to Wisconsin’s attorney general.

Chesebro has pleaded guilty in Georgia to a single felony count of participating in a conspiracy to file false documents for his role in organizing the pro-Trump electors. He has since met with other state investigators - including in Nevada and Arizona.

Chesebro, who aided the Trump campaign with legal challenges after the November 2020 election, has testified under oath that Troupis brought him into the former president’s sphere. He was eager to lend his expertise, records show.

In the immediate days after the election, Troupis and Chesebro mostly communicated about routine legal issues involving legal challenges and the recount Troupis was heading up for Trump. The first inkling of the elector strategy appears in the documents on Nov. 8, a day after the Associated Press had called the race for Biden.

Chesebro wondered whether there were legal grounds to challenge the result in Wisconsin based on various issues. If so - and if court proceedings were ongoing during the deadline for states to certify results, he wrote, “I don’t see why electoral votes” certified by the governor “should be counted over an alternative slate sent in by the legislature.”

The two attorneys became increasingly focused on the elector theory after Chesebro sent Troupis a memo in late November that pushed for the idea of pro-Trump roster of electors to organize in Wisconsin.

Troupis emailed Chesebro’s analysis to a Trump deputy campaign manager on Nov. 25: “Here is the memo we discussed about potentially moving the drop dead date back by several weeks in naming electors,” Troupis wrote. “This requires some very careful research for a given State, and some very precise actions the Trump electors must take in those states.”

As the calendar ticked toward Dec. 14, when electors were to meet in each state to cast their votes for president, Chesebro sent a new memo that Trump’s electors should meet in what he described as “six contested States, and send in the certificates” to official channels. He urged Troupis to get it to Trump’s campaign “and others involved with national strategy ASAP.” Chesebro added: “We’re only 7 days away now.”

In a garbled emailed response, Troupis indicated that he had “bypassed” the campaign staffer and was working on the issue. Troupis also texted Chesebro on Dec. 7: “I have sent it to the White House this afternoon. The real decision-makers.” He texted that he had also given it to Trump’s former chief of staff, Reince Priebus, who was from Wisconsin and had once led the state party there.

“So he might talk with the president,” Troupis wrote.

Troupis also made contact with Trump campaign adviser Boris Epshteyn. He described the Chesebro memos to him as documents that “I had prepared for me on appointing a second slate of electors in Wisconsin.” The plan, Troupis said, could be replicated, and the “key nationally would be for all six states to do it so the election remains in doubt until January.” But, he wrote, pro-Trump electors had to meet, vote and transmit their results on Dec. 14.

Two days later, Epshteyn wrote Troupis with a question from Trump attorney Rudy Giuliani.

Epshteyn wondered whether Troupis could “prepare a sample elector ballot for Wisconsin? If the answer is yes,” wrote Epshteyn, “how would you feel about preparing same sample ballots for PA, Georgia, Michigan, AZ, Nevada and New Mexico? If that’s difficult, we can have counsels in those states do it. Thank you!”

Troupis forwarded Epshteyn’s message to Chesebro and others: “KEN - would you be able to do this for the other States?” Chesebro agreed, and Troupis continued to provide direction, asking him to draft ballots and instructions for Trump electors on how and where to meet and how to mail paperwork to official government offices.

Pages of emails and text messages over the course of about three months - between early November and early February - detailed extensive portions of the attorneys’ correspondence with each other, with Trump’s campaign officials and key Trump allies and with state party officials around the nation as they scrambled to implement the plan and then ensure that the paperwork arrived in Washington on time.

On the eve of the Dec. 14 gathering of electors - as Republicans in Pennsylvania said they were uncomfortable portraying themselves as legitimate electors - Chesebro wrote to two Trump campaign advisers that the campaign “should indemnify electors against any legal costs,” even though he thought they had no legal exposure.

“A state might be able to punish faithless electors " who do not back their candidates, Chesebro wrote. “It can’t punish electors for being faithful, and backing their candidate through speech acts that expand congress’s options.”

Late that night, hours before electors gathered, Troupis texted Chesebro: “Is everything under control for tomorrow electors vote?”

Chesebro, who had flown to Wisconsin to attend the GOP electors signing ceremony there, replied that it was. Wisconsin’s Supreme Court decided a case involving the recount about an hour before Republicans met to sign their paperwork. The court upheld Biden’s victory, and Trump said he would appeal to the U.S. Supreme Court.

He said that he had fielded questions from those involved in Arizona, Georgia and Pennsylvania.

In Arizona, Chesebro had been working with then-state Republican Party Chair Kelli Ward and the party’s executive director, Greg Safsten, who was also an elector, according to a Dec. 12, 2020, email from Arizona-based attorney Jack Wilenchik, who was also working with them.

“Kelli knows how to get in touch with all the electors and has been coordinating with them I believe,” Wilenchik wrote.

In other emails, Ward asked about the process used to determine drafts of elector certificates that showed that GOP activist Nancy Cottle would serve as secretary of the effort and that Tyler Bowyer, a Republican national committeeman from the state and executive of a conservative group that targets young voters, would serve as chair. Chesebro replied that he had drafted the elector certificates and said that the certificates should “be edited to reflect who is actually elected to those positions.” Cottle became the chair, and another GOP activist became secretary.

In another email, Ward on Dec. 12 asked that the Trump campaign create and produce the documents and transmit them.

“I spoke directly to Rudy and told him we were working to make sure we accomplish what we need to do,” she wrote.

Emails show that Chesebro sent Ward, Safsten, Wilenchik and another Arizona attorney detailed instructions on how to carry out the plan and a draft of a news release, which was “borrowed from what the lead lawyer in WI (Jim Troupis) wrote & expects to release.” He instructed them to ensure that envelopes be sealed and labeled and to retain copies of ballots “as proof that the Electors did actually cast ballots for President & Vice President.”

The communications also include photos taken by Chesebro of Trump electors meeting to sign documents in Wisconsin, a video taken of the meeting, and of Republican lawyers and officials gathered inside an aircraft during a trip to Washington in mid-December. On that trip, which happened after the electoral college met, they met with Trump in the Oval Office and discussed the elector strategy. After that meeting, Chesebro texted Troupis a tweet from a conservative figure that referenced Trump’s Dec. 19, 2020, tweet about a “big protest” planned in Washington ahead of the Jan. 6, 2021, joint session of Congress.

“Be there, will be wild,” Trump’s tweet had said.

Chesebro texted Troupis: “Wow. Based on 3 days ago, I think we have unique understanding of this.”

Troupis sought information from Chesebro on what to expect as objections to the official certification of electoral votes in Congress played out. Chesebro invited Troupis to stay in an extra room he had booked at the Trump hotel, but Troupis was not planning to travel to Washington for the Jan. 6 certification.

On that day, Troupis encouraged Chesebro in a text to “Enjoy the history you have made possible today.” Soon after, they learned that Sen. Ron Johnson (R-Wis.) could not get the elector paperwork he was supposed to deliver to Pence “because it is not sealed,” Troupis texted. Chesebro texted photos of himself on the ground, smiling among a crowd and wearing a red Trump 2020 hat.

“Tear gas in the Capitol,” Troupis texted. Chesebro replied that he had caught a whiff.

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Patrick Marley and Adriana Usero contributed to this report.