By now, the saga of the false electors is relatively well known. After then-President Donald Trump’s election loss in November 2020, loyalists inside and adjacent to his campaign concocted a scheme to have pro-Trump electors in key swing states cast their electoral votes for the failed Republican ticket. Their objective was to tee up the possibility that Congress would count the fraudulent slates of electors on January 6, 2021, or otherwise use the existence of the fake votes to prevent the certification of President Biden’s victory. As the story is told in the final report of the House Select Committee to Investigate the January 6th Attack and subsequent indictments against Trump for attempting to overturn the election, the false electors plot was largely the work of lawyer Kenneth Chesebro, who sold the Trump Campaign on this idea and coordinated its implementation across multiple states. 

But that is not the whole story. In March, our team at Georgetown Law’s Institute for Constitutional Advocacy and Protection—along with our co-counsel at Law Forward and Stafford Rosenbaum, LLP—settled Penebaker v. Hitt, a historic lawsuit brought by two Democratic  Wisconsin electors against the ten individuals who fraudulently cast ballots for Trump and Pence, as well as two lawyers associated with the Trump Campaign. One of them was Chesebro himself, who already faces a public and legal reckoning for his role in the plot. The other was James Troupis, a top attorney for the Trump Campaign in Wisconsin who, until recently, had escaped significant national scrutiny. 

As part of our settlement agreement, we obtained thousands of emails, text messages, and other records from the defendants, including many from Troupis and Chesebro themselves. These documents, all of which are posted publicly, provide new revelations about the development of the false electors scheme, which should guide public understanding of this element of Trump’s multipronged attempt to nullify his defeat and unlawfully retain power. 

[Editor’s note: The Wisconsin documents are now integrated into a comprehensive timeline of the false electors scheme.]

This article explores three major themes exposed by the settlement: (1) the role of James Troupis; (2) the earlier-than-understood origins of the plot, just days after the election itself ; and (3) the design of the underlying scheme. 

First and foremost, these documents show that without Troupis, there would not have been a false electors scheme. Troupis leveraged his connections inside Trump’s orbit to operationalize Chesebro’s ideas. Second, the timeline presented by these documents shows how the false electors scheme was hatched much earlier than previously believed by close observers and continued in earnest through the violent insurrection on January 6th. Third, these documents make clear that the scheme was not—as now alleged by Trump’s defenders—a contingency plan in case courts overturned election results. On the contrary, this was a premeditated effort to use fraudulent slates of electors to introduce uncertainty and chaos into the Joint Session, no matter what the courts ruled. To put it simply, the new information obtained as a result of the Penebaker litigation shows that the false electors scheme was not just a lawyerly subplot to a haphazard coup attempt; rather, it was the centerpiece of Trump’s well-orchestrated pressure campaign to dismantle democracy. 

“Cloud of Confusion”

In Chesebro’s very first November 8th email to Troupis—weeks before the Trump Campaign’s legal efforts to challenge the election results foundered in courtrooms across the country—all three of those themes were vividly illustrated. Chesebro wrote that if “various systemic abuses can be proven,” an “alternate slate [of electors] sent in by the legislature” could be counted by Congress. “At minimum,” he wrote, “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.” 

This email, sent only five days after the election, undermines the main argument made by  Trump allies and legal academics alike as public scrutiny on the false electors scheme increased: that the plot was not as dangerous or anti-democratic as it may appear, because there was some historical precedent for competing slates of electors to vote when there was ongoing litigation that could change the outcome of the election. But the origins of this scheme had nothing to do with litigation. Chesebro presented his false electors plot as a way to wreak havoc on January 6th, not because of any realistic hope that the courts would deliver victory to Trump. Troupis was eager to nurture it.

Throughout the next week, Chesebro and Troupis continued to text about the emergent scheme, with Chesebro very much assuming the role of a junior associate (“[I] did a memo, which I hope I can get to you securely”) to Troupis as senior partner (“[I am] headed to Washington in the AM to brief the White House.”). When Chesebro sent Troupis the now-infamous memorandum that the more senior lawyer “requested,” he urged Troupis to share it with the broader Trump Campaign, saying, “I think we should be sure national lawyers are aware of these points.” A few days later, Troupis did just that, and sent Chesebro’s memo to Trump Campaign attorney Justin Clark. 

These first exchanges also mark the start of a pattern that is the most startling revelation from the Penebaker settlement; namely, how successfully Troupis was able to hide his role in the false electors scheme. While Chesebro has endured years of scrutiny—and criminal exposure—as a chief architect of this effort, it is very clear that Troupis is the reason why Chesebro was able to put his plan into motion in the first place. On Dec. 7, 2020, after Chesebro sent Troupis another memo “on why it’s important all electors vote in all 6 contested states,” Troupis “bypassed” Clark and told Chesebro, “I have sent it to the White House this afternoon. The real decision makers.”

But Troupis did not stop there. He then reported to Chesebro that he also shared the memo with former Trump Chief of Staff Reince Priebus, “so he might talk with the President.” And he emailed senior Trump advisor Boris Epshteyn writing, “Our strategy, which we believe is replicable in all 6 contested states, is for the electors to meet and vote.” He then volunteered Chesebro’s help if Epshteyn wanted to take the strategy further, an offer which Ephshteyn was only too happy to accept. 

“An Excellent Summary of the End Game”

As Troupis was sending out these missives, Chesebro was eagerly reassuring his Trump World patron that the false elector strategy was an alternative to litigation, rather than a contingency. “Court challenges pending on Jan. 6 really not necessary,” he wrote on Dec. 8. “I think having the electors send in alternate slates of votes on December 14 can pay huge dividends even if there is no litigation pending on Jan. 6.” Troupis not only agreed with this flagrantly anti-constitutional analysis, saying it is “an excellent summary of the end game,” but also reassured Chesebro that he had shared this plan with Wisconsin Senator Ron Johnson, who was a prominent advocate of Trump’s fraudulent election claims. Chesebro replied enthusiastically, writing, “The prospect of extending the fight into January is exciting!”

Together, Chesebro and Troupis went a long way toward ensuring that would happen. Troupis connected Chesebro directly with Epshteyn and Clark, which catapulted the newcomer into the frantic hub of Trump’s attempt to subvert the election. We obtained dozens of emails that showed the depths of Chesebro’s involvement with the scheme in the days leading up to Dec. 14, when the false slates of electors were scheduled to meet. He communicated with Republican officials and elector candidates in the six contested states, as well as Trump lieutenant Rudy Giuliani. Emails and texts unearthed between Chesebro and senior campaign officials illustrate how distant the scheme was from a contingency plan related to litigation; for example, campaign staffer Mike Roman texted Chesebro “fuck these guys,” in reference to Pennsyvlania electors who wanted to insert language conditioning their votes on subsequent court victories. As a result of this pushback from some state officials, Chesebro did indeed add contingency language to alternate certificates in New Mexico, and acknowledged in an email Trump Campaign officials, “Might be good to have it [new qualifying language] added in all states.”  The fact that Chesebro understood the utility—and perhaps, legal wisdom—of such conditional language only makes his actions more galling. He plowed ahead with the false electors scheme, despite the fact that conditional language was not added in most of the contested states, Wisconsin included.

For example, working with the Trump Campaign, Chesebro devised illicit ways around concerns raised by electors in Arizona who, according to Chesebro, were “concerned it could appear treasonous for [them] to vote on Monday if there is no pending court proceeding” That same day, Giuliani, through Chesebro, suggested that Wilenchik “file a petition for certiorari in the Supreme Court as a pretext to claim that litigation was pending in the state, to provide cover for the convening and voting of [Trump’s] fraudulent electors there,” according to the federal indictment. (In the end, contingent language was included only in the false certificates signed in Pennsylvania and New Mexico.)

As Chesebro was welcomed into the inner workings of the efforts to overturn the election, it is clear that he still wanted to stay close to Troupis, the man who enabled his dizzying rise through the ranks of Trump-allied lawyers. On Dec. 10, he emailed Troupis, “Just wanted you to know that the national people are totally on board with your push for the electors to vote!!” 

Troupis, meanwhile, remained engaged in setting up the meeting of the false electors in Wisconsin, which Chesebro attended on Dec. 14. Chesebro excitedly texted Troupis saying, “WI meeting of the *real* electors is a go!!!” During the meeting, Chesebro continued to send Troupis updates and pictures from the event, to which Troupis responded with a thumbs-up emoji. 

“History is Made!”

Of course, we already know what happened next. The false electors met, and in multiple states—including Wisconsin—signed documents that fraudulently asserted that they were the duly appointed electors for their state, whose votes should be counted on January 6. But in the documents obtained in our settlement, we learned much more about how the false elector scheme was really only beginning once those false votes were cast. 

Almost immediately after the Dec. 14 meeting, Troupis and Chesebro met with Trump in the Oval Office, where Troupis told Trump there was “zero hope” for winning Wisconsin through litigation. Nevertheless, his efforts to undermine the results continued.  On Dec. 21, he connected Chesebro with John Eastman, who was busy orchestrating a pressure campaign on Mike Pence that would last until the Capitol siege itself. Although Eastman has rightfully received the lion’s share of credit for this pressure campaign, Chesebro and Troupis were responsible for laying the groundwork. A week after they were put in contact with Eastman, Troupis instructed Chesebro to work on a “step by step, easy to understand, non-lawyerly process for the Senators/Congressmen and VP to follow on the 6th.” Chesebro, of course, complied. The two men continued to speak with each other and Trump Campaign officials through New Year’s Day about the prospects for disrupting and delaying the Joint Session.

As January 6 approached, Chesebro—now deep in the Trump Campaign’s inner sanctum—was still trying to get the fraudulent certificates from Wisconsin delivered to Pence himself. While he arranged to meet a junior Republican Party staffer who was flying to D.C. with the certificates, he advised his campaign contacts to ask Troupis to “check immediately with Ron Johnson” about relaying the documents to Pence. Troupis did exactly that. He was texting with Johnson on the morning of January 6, just hours before the attack began, saying, “We need to get a document on the Wisconsin electors to you for the VP immediately.” When Johnson told Troupis that was not possible, Troupis texted Chesebro immediately with the update. 

While they were texting, Trump was inciting his supporters, gathered on the Ellipse and the National Mall, to march on the Capitol and fight. Chesebro himself was in the crowd, sending pictures to Troupis, who replied with encouragement: “Enjoy the history you have made possible today!”; “Well done Ken! History is made”

“Tear Gas in the Capitol” 

The documents we obtained as part of the Penebaker settlement expand the public’s understanding of the plot to overturn the 2020 election, and reinforce some of the most damning and sweeping conclusions that have already been made about the schemes that eventually led to death and destruction on January 6. For one, these new communications illustrate that Chesebro and others associated with the Trump Campaign understood that  their legal stratagems were not  “contingent” or “conditional” on judicial intervention. From the very first days after Trump’s defeat, the false electors scheme was promoted by its chief architects as an end run around doomed litigation, not preparation for its success. 

Even more importantly, perhaps, the unprecedented view inside Troupis’s and Chesebro’s communications fortifies the ugly truth, already exposed by the House Select Committee’s investigation, that the legal elements of Trump’s post-election plots cannot and should not be disentangled from the flagrantly autocratic putsch that nearly derailed our democracy. These two Wisconsinite lawyers, despite long and successful careers, threw themselves headfirst into an effort they knew would not result in Trump’s victory unless some extra-legal intervention—whether by state legislators, Vice President Pence, or an angry mob—made it so. As White House lawyer Eric Herschmann warned in an internal text message, their plan was one of “Certifying illegal votes.” 

The possibility that their work could have had a lawful pretext cannot hide the reality that it was deeply, incontrovertibly lawless. 

Of course, the culmination of this lawlessness came on January 6 itself, when President Trump directed his supporters to march on the Capitol and “fight like hell” to pressure lawmakers to bend to the lies that Troupis and Chesebro had knowingly peddled for months. We now know that Chesebro was in the crowd of Trump’s supporters that day. As the day spiraled into bloodlust and insurrection, Chesebro continued to communicate with Troupis, the man who had given him a starring role in the events leading up to that day. In texts we obtained, he is excitedly sending photos of himself to Troupis, including one with infamous conspiracy theorist Alex Jones, with whom he marched toward the Capitol (see also CNN report). In response to one picture, Troupis sent a clapping emoji. 

It’s only after violence breaks out in the Capitol that Troupis’s jubilation turns to concern. “Tear gas in the Capitol,” he warns Chesebro, as it became clear to the world that their months of anti-democratic scheming had facilitated an unprecedented moment of anti-democratic violence. Chesebro quickly responded that he caught a whiff, “Lol.

Top image: Trump campaign attorney James Troupis testifies during a hearing called by Chairman of the Senate Homeland Security and Governmental Affairs Committee, Sen. Ron Johnson (R-WI) to discuss “election irregularites” in and the 2020 election. December 16, 2020 on Capitol Hill in Washington,DC. (Jim Lo Scalzo/Pool/AFP via Getty Images)