Kenneth Chesebro was eager to help.
It was five days after the 2020 presidential election and Joe Biden was projected to defeat Donald Trump and win Wisconsin’s 10 electoral votes. Trump’s campaign was requesting a recount. Chesebro, a little-known Harvard-educated lawyer, believed there were abnormalities in the election and emailed Jim Troupis, a friend and former Wisconsin judge, to offer to help with any of the campaign’s legal efforts.
Chesebro tacked on a thought at the end of his message. If there were still questions about irregularities while Wisconsin’s members of the electoral college cast their votes for Joe Biden, Congress might not have to accept the result of the election.
“If these various systemic abuses can be proven, and found to be pivotal in a court decision and/or detailed legislative findings, I don’t see why electoral votes certified by Evers (at least if court proceedings are still pending on the ‘safe harbor’ days) should be counted over an alternative slate sent in by the legislature, whose decisions should have primacy,” he wrote in an email on 8 November 2020. “At minimum, with such a cloud of confusion, no votes from WI (and perhaps also MI and PA) should be counted, perhaps enough to throw the election to the House.”
The short email, released Monday as part of a civil suit settlement, was the earliest seed of what would come to be known as the “fake electors” scheme – a national effort led by Chesebro to get Congress to reject legitimate slates of electors in favor of pro-Trump slates. It was a critical piece of Trump’s anti-democratic effort to overturn the 2020 election and now lies at the center of two criminal cases against the former president.
Chesebro has pleaded guilty to conspiracy to file false documents, a felony, in Georgia, and was sentenced to five years of probation and $5,000 restitution. He is an unnamed and unindicted co-conspirator in the federal election interference case against Trump. Troupis, who sits on a judicial ethics panel in Wisconsin, has not been criminally charged for his role in the scheme.
“The resolution of this litigation provides much-needed transparency into how the fraudulent electors scheme was conceived and developed, and it exposes the key roles both Troupis and Chesebro played not only in executing the scheme in Wisconsin, but also around the nation,” Law Forward, Georgetown University Law Center’s Institute for Constitutional Advocacy and Protection (ICAP) and Stafford Rosenbaum, the legal groups who brought the civil case, said in a statement.
Chesebro did not immediately return a request for comment.
“It is the duty of lawyers to vigorously represent their clients, regardless of their popularity, within the bounds of the law. Our representation was vigorous and ethically appropriate,” Troupis said in a statement.
Five days after his email, on 13 November, Troupis invited Chesebro to be part of the “legal briefing” team. Chesebro, who had been peppering Troupis with tweets he came across, replied that he was available to join “any call today on 20 mins notice”.
“In the meantime, I’m still reading up on election law,” he added.
Five days later, Chesebro sent what is now a well-known memo outlining the fake elector scheme. With the subject line “The Real Deadline for Settling a State’s Electoral Votes”, the document offered a legal justification to throwing out the valid votes of Americans across the country and would become a roadmap for what was to unfold over the next few weeks.
In the emails, Chesebro floated multiple avenues to challenge the election in Wisconsin – attempting to solve the puzzle of actually getting a court to side with them.
“I should add a note about a more aggressive version of this strategy,” he wrote to Troupis on 19 November, arguing that the state legislature could justify choosing its own electors by casting doubt on the official process – which had changed during the pandemic to expand absentee voting. “The beauty of this is that the Republican legislators, if they adhere carefully to this theory, can emphasize that they’re simply acting in the interests of the State,” he added.
Clever legal arguments would be important, but so would the perception, among Republican voters, that the 2020 election had been tainted by rampant fraud.
“The whole idea is a long shot. Probably it would only be viable if by early December there was a palpable sense among conservatives that there was a concerted effort by Democrats to steal this election in multiple states,” he wrote.
Chesebro pointed to numerous pandemic-era practices as potential legal challenges: “Democracy in the Park” events staffed by poll workers in Madison parks where voters could drop off their ballots ahead of election day and the use of ballot “drop boxes” were two particularly troubling practices, in Chesebro’s mind, and could form the basis for an objection.
The documents also show how Chesebro sought to use conservative media to get the attention of conservatives on the Wisconsin supreme court. As they discussed various theories of wrongdoing in 18 November, Chesebro suggested “tipping off” conservative radio hosts. “Mostly to maximize the chance that [supreme court of Wisconsin] justices hear about this quickly and prejudge the case?” he wrote, adding a winking emoji to the text.
In mid-December, after the Wisconsin supreme court declined to overturn the state’s election results, Chesebro sent Troupis a screenshot of a text that appears to joke about killing Brian Hagedorn, a conservative justice who cast a critical vote in the case. “We’re thinking of inviting Hagedorn on the plane and solving that problem at high altitude, over water …” the message says. It’s not clear who the message is from.
Outside of the legal strategy, the documents also show how Chesebro was willing to assist with any detail, no matter how small – from brainstorming a media strategy to offering to coordinate on logistics. He drafted a press release on the Wisconsin alternate electors meeting, only backtracking when Michael Roman, a top Trump aide, made clear in a 14 December email that the plan was not to be shared with the media.
Chesebro offered an alternative idea – rather than a local media blitz, a message about their effort could come from the top – “Like a tweeted statement by Ellis, and follow up on-camera explanation by RG, and or follow up tweet by the President?” he replied, apparently in reference to Trump campaign lawyers Jenna Ellis and Rudy Giuliani. “Much wiser heads on that sort of thing than me!”
Later, as he and Roman tried to figure out how to get the fake electors documents to the Capitol on January 6, Chesebro offered different flights and routes a congressional aide could take to fly into Washington.
Those who know Chesebro have been baffled at how he got caught up in the fake electors scheme. The messages hint at a sense of excitement in being involved with Trump and his closest aides. After Troupis and Chesebro met with Trump in the Oval Office on 15 December, Chesebro texted Troupis a picture of Troupis on what appears to be a private plane.
A few days after that meeting, Trump sent out a tweet inviting supporters to Washington on January 6. “Be there, will be wild,” Trump said. Chesebro sent the tweet to Troupis and wrote: “Wow. Based on 3 days ago, I think we have a unique understanding of this.”
And on January 6, Troupis praised Chesebro’s work as senators began to object to the electoral college vote. “You got Arizona. Well done Ken! History is made,” he wrote in a text message. Chesebro replied with a picture of him on the mall smiling in front of the Washington monument. He later followed up with a smiling selfie of him and the far-right host Alex Jones. “Hanging with Alex Jones,” Chesebro wrote. “Lol. I told him to put you on his show.”
The next morning, after the attack on the Capitol, Chesebro suggested Trump surrogates should lay blame on antifa and poor security that was under the control of Mitch McConnell and Nancy Pelosi. He also suggested Trump could put the episode behind him by inviting Biden and Harris over for coffee on the morning of the inauguration. “He could lighten it up with a couple of well-placed jokes.”
About an hour later, he said it was “stupid to have a rally on Jan. 6”. “Original plan was Jan. 5 right? Would have been perfect to have a Jan. 5 rally, then told people to go home, so focus would be on debate in Congress.” He also added Mike Pence was to blame for giving Trump hope of overturning the election and then not following through.
On 22 February, the US supreme court dismissed a request filed by Troupis and Chesebro on behalf of the Trump campaign to revisit the Wisconsin election results.
“So sorry,” Chesebro wrote.
“You’re [sic] work was incredible Ken. I am honored to have been a part of it,” Troupis replied.
“I am honored you invited me to help at all. Would have been worth it even if we’d gotten no votes and had never met the President – just being on a team with the guts to represent someone with an important case who other lawyers shunned was worth it,” Chesebro said.
