Docs reveal new details of Trump lawyer's fringe push to overturn 2020 election

A trove of documents released this week reveal extraordinary new details about the role of Kenneth Chesebro — a once-obscure conservative attorney — in driving the strategy to keep Donald Trump in power despite his defeat in the 2020 election.

Communications between Chesebro and a top Trump campaign lawyer in Wisconsin, Jim Troupis, show that Chesebro argued just days after the Nov. 3, 2020 election that creating a “cloud of confusion” by submitting dueling slates of electors would be enough to keep Joe Biden from becoming president.

The 1,439-page document dump, released as part of a settlement in a lawsuit brought by Democratic officials in Wisconsin, also provides a deeper glimpse into the mind of Chesebro, who became known as “co-conspirator 5” in Trump’s Washington, D.C. indictment brought by special counsel Jack Smith, and pleaded guilty to conspiring to file false documents in a related case brought by Georgia prosecutors.

The emails and texts show Chesebro was fixated on the areas of the transfer of power that had few guardrails, like the process of counting presidential electors by Congress on Jan. 6, 2021. Those vulnerable areas, Chesebro realized, could be exploited by Trump allies willing to advance unprecedented and fringe legal theories.

At each turn, as courts blew up aspects of his strategy, Chesebro clung to hope that his plan was succeeding. And when it ultimately fell apart, he privately lashed out at former Vice President Mike Pence, who he claimed blindsided the Trump team by refusing to acquiesce to their radical plan.

Here’s a look at some of the significant insights in the new documents:

Chesebro’s post-riot reckoning

Chesebro started Jan. 6 on a high, claiming loftily that he and his colleagues had made history by setting in motion a plan that might block Biden’s victory. He sent a picture of himself among Trump supporters gathered at the Washington Monument at 1:24 p.m. that day, just after Trump had finished addressing his supporters nearby.

Chesebro later marched to the Capitol amid the riot, joining a group that traveled with InfoWars host Alex Jones as they traversed the restricted Capitol grounds but did not enter the building.

Hours after the National Guard helped clear the Capitol of the last remaining rioters and a beleaguered Congress reconvened to finish certifying Biden’s victory, Chesebro began trafficking in conspiracy theories about “antifa” perpetrating the attack on the Capitol. He also suggested that Trump “put this behind him” by inviting Biden and VP-elect Kamala Harris for coffee on inauguration day.

“He could lighten it up with a couple of well-placed jokes,” Chesebro said in texts to Troupis, a flagrant misread of the moment, “like he wants to make sure Joe feels comfortable calling him for advice in the challenging days ahead. Or we invited Joe over for coffee [because] he wants to be sure Joe invites him four years from now.”

Most notably, in the same chain of texts to Troupis, Chesebro lashed out at Pence, who he said was “a lot to blame for this fiasco” and proposed “an effort to criticize Pence for deceitful conduct that led to this chaos.”

In the weeks leading up to Jan. 6, egged on by Chesebro and other allies like Rudy Giuliani and John Eastman, Trump had pressed Pence to block the certification of Biden’s victory in his role presiding over the joint session of Congress. But Pence ultimately rebuffed the effort.

“I now think Pence had decided by then not to do anything to press the envelope or create a test case, but decided not to be straight with the president,” Chesebro wrote. “If I'm right, Pence gave him false hope. He allowed Trump to hear of valid legal theories from Rudy and Eastman which gave him hope, which was crushed when Pence suddenly crushed them at the end. Why did Pence do this?”

‘Even if Trump lost all the legal cases’

Chesebro’s strategy to keep Trump in power hinged on the Trump campaign delivering “alternate” slates of presidential electors to Congress — from six states won by Biden — in order to create a controversy that Pence could cite to refuse to count Biden’s electors. To justify the alternate slates, Chesebro urged the campaign to ensure it had legal challenges pending in each of those states so they could claim that the “alternate” electors were just a contingency plan.

But Chesebro also told Troupis that those lawsuits did not need to be pending on Jan. 6, when Congress met to count electors, because nothing would prevent GOP lawmakers from refusing to count Biden’s votes.

“On reflection, I think having the electors send in alternate slates of votes on Dec. 14 can pay huge dividends even if there is no litigation pending on Jan. 6,” he wrote in a Dec. 8 email. “There's nothing in the Constitution … to prevent the Senate now, if it wishes, from holding hearings, with testimony, to decide if the election was stolen in one or more States, before voting on which slate of electors should be counted — again, even if Trump lost all the legal cases, and none are still pending.”

Filibustering the joint session

Chesebro spilled much more ink than previously known on figuring out a way to work around the long-settled procedures of the Jan. 6 joint session of Congress — particularly its limits on the length of debate when objections were raised to electors from any particular states. The Electoral Count Act, the 1887 law that has governed presidential transitions for 137 years, requires no more than two hours of debate per state, with no lawmaker speaking for more than five minutes.

Chesebro’s efforts to prolong the Jan. 6 session — and to use the ensuing pressure to whip Republicans in line against counting Biden’s votes — depended almost entirely on Pence agreeing to find a way to circumvent those rules.

“Anything Pence can do unilaterally to slow things down will obviously be of enormous benefit to senators who support Trump but who, standing alone, would find it difficult to resist pressure” to end debate, Chesebro wrote in a Dec. 8 email. “If he has the will to do it, Pence could stand as Horatius at the Bridge,” Chesebro continued, “and help ensure adequate time for debate, shielding the Republican senators from a politically dicey cloture vote.”

Chesebro’s concern about timing became more acute when he began focusing on the minutiae of the Jan. 6 session — including Congress’ century-old habit of adopting the rules of the session three days beforehand via a resolution passed in both the House and the Senate. POLITICO highlighted the role of this resolution days before Chesebro began worrying about it. And when the resolution passed without a whisper of debate, Chesebro began searching for ways Pence could still dodge the limits Congress imposed upon itself. He circulated to Troupis a POLITICO link to the new session rules.

“Makes it hard [to] force Pence to allow for unlimited debate,” Chesebro lamented.

Hoping against hope

Everywhere he looked, Chesebro saw signs of hope that his plan was working, even in moments that appeared to be setbacks.

“Trump sounds so forceful that maybe Pence has actually agreed to do something,” he wrote to Troupis early in the day on Jan. 6, remarking on a speech in which Trump repeatedly criticized Pence for his apparent unwillingness to acquiesce to Trump’s plan.

When Sen. Ron Johnson (R-Wis.) told Troupis that he was unable to deliver a slate of electors directly to Pence because he couldn’t accept “unsealed” mail, Chesebro responded that this may in fact be a clever ploy by Pence to force a delay.

And on Jan. 4, when Sen. Chris Van Hollen (D-Md.) foreshadowed Democrats’ plans to raise concerns about Trump’s newly revealed phone call with Georgia election officials — which would become a centerpiece of the Fulton County criminal case against Trump — Chesebro saw an opportunity to use it to their advantage.

“If Dems do raise this in a debate, they'll depart from the Act's narrow constraints. Maybe Pence could take the view that this opens the door to unlimited debate on Georgia,” he said.

Chesebro and Troupis played out one particularly radical scenario in which neither candidate earned 270 electoral votes on Jan. 6, triggering a “contingent election” for president in the House. They theorized that then-Speaker Nancy Pelosi would refuse to hold a vote because Republicans might prevail in the unusual state-by-state count and that she might become acting president by default.

“But none of this happens unless Pence freezes the count,” Chesebro added.