The memos and emails reveal the underpinnings of a desperate strategy to assemble slates of fraudulent electors, first to preserve legal options and later to foment a conflict on Jan. 6, 2021, that might lead to Trump retaining the presidency. Along the way, Chesebro concocted methods for avoiding unfavorable court rulings, enlisting friendly allies in Congress to grease the skids and ultimately counting on Mike Pence to take “bold” steps to derail the impending Biden presidency. (Chesebro, through his lawyer, did not immediately respond to a request for comment.)

Here’s a chronology of Chesebro’s key documents and proposals, which show how his thinking evolved from philosophical discussions to operational plans — and at times veered into outright fantasy.

NOV. 18, 2020 MEMO: Chesebro’s initial foray into Trump world’s upper echelons came as states prepared to certify their election results. Chesebro was advising Wisconsin-based Trump attorney Jim Troupis about a legal strategy for challenging the results there in court.

Here, Chesebro first emphasized that Jan. 6, 2021 was the real “hard deadline” for courts to rule on Trump’s election challenges. But he stressed that in order to sustain legal challenges to Wisconsin’s results, a slate of pro-Trump electors must convene on Dec. 14, 2020 and cast ballots as though they were legitimately elected.

“It may seem odd that electors pledged to Trump and Pence might meet and cast their votes on December 14 even if, at that juncture, the Trump-Pence ticket is behind in the vote count,” Chesebro wrote. “However, a fair reading of the federal statutes suggests that this is a reasonable course of action.”

Chesebro noted that if courts ruled in Trump’s favor, Congress may only be able to count electoral votes cast by the legally prescribed deadline of Dec. 14. In other words, it was a contingency plan while lawsuits were pending.

DEC. 6, 2020 MEMO: By early December, Chesebro’s thinking had shifted radically. A memo first described in the special counsel’s indictment, and publicly revealed Tuesday by The New York Times, showed that Chesebro began to view the pro-Trump electors as part of a strategy to derail the transfer of power altogether — not simply as a backup plan for the courts.

The memo, also directed to Troupis, suggested that the Trump campaign assemble alternate slates of electors in six states where legal challenges were pending.

“I’ve mulled over how January might play out, and it seems feasible that the Trump campaign can prevent Biden from amassing 270 electoral votes on January 6, and force the Members of Congress, the media, and the American people to focus on the substantive evidence of illegal election and counting activities in the six contested states,” Chesebro wrote.

He described three essential criteria: 1) Meetings of the pro-Trump elector slates on Dec. 14 in all six states: Arizona, Georgia, Michigan, Nevada, Pennsylvania and Wisconsin (a seventh, New Mexico, would be added later); 2) The existence of pending litigation in those states that could conceivably reverse the outcome; 3) A declaration by Pence that only he could decide which electoral votes to count on Jan. 6, 2021, when he presided over the joint session of Congress to certify the election.

“I’m not necessarily advising this course of action,” he added, describing it as a “bold, controversial strategy.”

Chesebro also used the memo to suggest that Trump’s elector slates meet secretly to avoid protest. At the same time, he wrote, the campaign should be prepared to characterize the meetings as “routine” contingency planning for potential legal victories.

DEC. 9, 2020 MEMO: Days after advising the campaign to convene its false elector slates, Chesebro provided a plan to operationalize the strategy. In a third memo to Troupis, Chesebro outlined the federal and state laws governing the meetings of the electors and how the Trump campaign could attempt to comply with those requirements in order to keep alive the chance that they would be counted by the courts or Congress.

Chesebro notes that no state legislatures had certified these alternate slates — Trump and his allies were still leaning on GOP legislators to take that step — but that the pro-Trump electors should meet anyway to cast contingent ballots. However, in some states, valid electors were required to meet in specific venues or under the guidance of specific state officials like the governor or secretary of state.

He noted the rules could make assembling alternate slates “very problematic” in Nevada and “somewhat dicey” in Michigan and Pennsylvania.

DEC. 13, 2020 NOTES TO RUDY GIULIANI: On the eve of the elector meetings, Chesebro typed up notes to Rudy Giuliani, a substitute for a memo he said he lost due to a “reboot on the hotel computer.” This document, which he forwarded to Eastman on Jan. 2, 2021, was publicly revealed last year, after a federal judge determined it constituted evidence of a likely crime.

In this memo, Chesebro laid out what he called the “President of the Senate” strategy — a reference to Pence’s role on Jan. 6, 2021. He strongly advocated that Pence take the position that he had ultimate authority to determine which electoral votes to count or ignore. Even if it couldn’t prevent Biden’s election, Chesebro reasoned, Pence’s declaration could help obtain leverage that might be used to broker some alternative outcome.

Most notably, Chesebro’s memo laid out a pre-Jan. 6 timeline that would help facilitate the plan. It began with a Jan. 3-5 plan for friendly GOP lawmakers to hold hearings highlighting the ambiguities of the Electoral Count Act — the law that has governed the transfer of power since 1887 — and the vice president’s role in counting electoral votes. The goal was to feature testimony from allied legal scholars to “buttress the substantive basis for the President of the Senate later refusing to count votes from those states, absent more needed scrutiny.”

On Jan. 6, Chesebro said, Pence would announce his recusal from presiding over the joint session of Congress, citing the unconstitutionality of the Electoral Count Act as well as a conflict of interest because of his candidacy for reelection. This, Chesebro contended, would “insulate” Pence from charges of making a self-serving decision and leave the matter ostensibly in the hands of a senior Republican senator. Then, after beginning to count electoral votes from an alphabetical list of states, that senator would refuse to count the votes from Arizona, citing the competing slates of electors. If Arizona wants to be counted, this senator would say, it would either have to “rerun” its election or allow for more judicial review of the outcome.

Chesebro predicted controversy and conflict would ensue from this step — and noted Biden could still emerge victorious if the conflict made its way to the Supreme Court. But he said the Supreme Court might refuse to step in, avoiding the clash between the political branches. In that scenario, he said, with the White House and Congress at loggerheads, then-Speaker Nancy Pelosi might become acting president on Jan. 20. But another outcome, he said — one that appears even more far-fetched in hindsight — might play out: Trump could quit the race in exchange for a negotiated deal to make Pence president.

“In this situation,” Chesebro wrote, “which would be messy and unpalatable to many … it doesn’t seem fanciful to think Trump and Pence would end up winning the vote after some legislatures appoint electors, or else that there might be a negotiated solution in which the Senate elects Pence vice president and Trump agrees to drop his bid … so that Biden and Harris are defeated, even though Trump isn’t re-elected.”

DEC. 23, 2020 EASTMAN EMAIL TO BORIS EPSHTEYN: Eastman distilled his own analyses and Chesebro’s advice into a pair of memos he brought to Trump and Pence. On Dec. 23, Eastman shared a draft of one of those memos with Trump adviser Boris Epshteyn, cc’ing Chesebro on the message. Eastman signaled to Epshteyn that Chesebro had edited the memo. He also noted that he and Chesebro agreed that congressional hearings to bolster their case were no longer advisable because they could “invite counter views that we do not believe should constrain Pence (or Grassley).”

“Better for them to just act boldly and be challenged,” Eastman wrote.

This step, Eastman noted, would likely result in the Supreme Court refusing to take up the case “on nonjusticiable political question grounds” — in other words, a win for Trump by default.

DEC. 31 2020 EMAIL FROM CHESEBRO TO EASTMAN AND OTHER TRUMP LAWYERS: Chesebro was also involved in the campaign’s broader legal strategy to try to get a friendly judge to give judicial imprimatur to the notion that the election results were in doubt — especially in Georgia. While Trump worked, via Justice Department official Jeff Clark, to get the department to similarly use its institutional power to cast doubt on the results, Chesebro suggested targeting efforts at Supreme Court Justice Clarence Thomas. Thomas is the so-called “circuit justice” for Georgia and neighboring states, meaning he performs the initial review of emergency appeals arising from that part of the country.

“The point is to have the court say that probably the election was void, which should be enough to prevent the Senate from counting the Biden electoral votes from Georgia, right?” Chesebro said in an email to Eastman and a larger group of lawyers working on Trump’s post-election legal efforts.

“Possibly Thomas would end up being the key here — circuit justice, right? We want to frame things so that Thomas could be the one to issue some sort of stay or other circuit justice opinion saying Georgia is in legitimate doubt,” Chesebro wrote. “Realistically, our only chance to get a favorable judicial opinion by Jan. 6, which might hold up the Georgia count in Congress, is from Thomas — do you agree, Prof. Eastman?”

Eastman, a former Thomas clerk who had at times been in touch with his wife Ginni during the post-election period, replied: “I think I agree with this. If the court were to give us ‘likely,’ that may be enough to kick the Georgia Legislature into gear, because I’ve been getting a lot of calls from them indicating to me they’re leaning that way.”

JAN. 1, 2021 NOTES TO EPSHTEYN AND EASTMAN: Chesebro’s last known message ahead of Jan. 6 was a set of 14 talking points for congressional Republicans to challenge the limits imposed on them by the Electoral Count Act. It was his most specific and granular advice yet regarding the minutiae of Congress’ procedures.

In particular, Chesebro advocated for friendly GOP lawmakers to resist the law’s limit of just five minutes of debate per lawmaker — with a maximum aggregate debate time of two hours — during formal challenges to a state’s electors.

Chesebro reasoned that Pence could side with the objecting lawmakers and agree that debate could not constitutionally be limited without a cloture vote of 60 senators.

“It might be politically painful for a Republican to vote to cut off debate,” Chesebro contended, adding, “It could take hours of debate on each state before a filibuster is overcome.”

But Chesebro noted one huge, little-understood hurdle: Every four years — for decades — Congress has affirmatively bound itself to the strict limits of the Electoral Count Act by adopting a “concurrent resolution” agreeing to abide by the terms of the 136-year-old law. If that resolution were passed on Jan. 3, 2021, he noted, it would remove any possible challenge to the constitutionality of the procedures.

As a result, Chesebro advocated for a lawmaker — like Sen. Josh Hawley (R-Mo.) — to attempt to block the concurrent resolution, forcing a debate and vote. Chesebro said this plan would be useful to determine the whip count among Senate Republicans for challenges to the election results.

Chesebro also sought to reconcile his call for lengthy debates with his larger argument that Pence — not Congress — got to determine which electors to count. He said Pence could simply allow the debates to proceed without conceding their legitimacy, buying time for the Supreme Court or state legislatures to act.

Ultimately, no lawmaker objected to the concurrent resolution, which was adopted unanimously on Jan. 3, 2021.