One individual stands out among the 18 Donald Trump acolytes who were indicted in Georgia this week over their participation in the former president’s alleged racketeering enterprise to overturn the 2020 election.
He is distinct not for his chutzpah and braggadocio – those qualities are trademarked by Trump. Instead he stands out for the opposite characteristics: his demure, scholarly demeanor that has left those who have known him utterly baffled by his eruption from a left-leaning attorney working in relative obscurity into a key figure in the glaring lights of a historic criminal prosecution.
Kenneth Chesebro is not your regular Trump guy.
“Of all people to be involved in this craziness, Ken seems to be the least likely,” said the lawyer and legal analyst Jeffrey Toobin who studied with Chesebro at Harvard law school in the 1980s. Toobin, who has written about his old classmate for Graydon Carter’s digital journal, Air Mail, added that he did not seem to have the bearing to play such a lion-sized role in the Trump election subversion scandal.
“He was such a quiet and undemonstrative person – very low-profile.”
Yet Chesebro features heavily in Jack Smith’s federal indictment of Trump. He is name-checked by the special counsel 13 times under the codename “Co-Conspirator 5”, and though he has not been charged in the federal case, Chesebro is directly accused of devising and implementing the fake elector plot which lay at the center of Trump’s efforts to subvert the 2020 election.
Chesebro is centrally cast again in this week’s sprawling indictment issued by a grand jury in Fulton county, Georgia. This time he has been charged with seven felony counts – one under the state’s racketeering law that targets organized crime groups, and six for acts of conspiracy relating to the fake electors and the pressure campaign to cajole vice-president Mike Pence into blocking Joe Biden’s victory on 6 January 2021.
Democracy groups credit Chesebro with being the architect of the audacious plan to send fake electors to Congress from states Trump had lost. “In our estimation, based on publicly available information, Kenneth Chesebro was the central mind behind the fake elector idea,” said Michael Teter, managing director of the 65 Project, a non-profit which seeks to hold lawyers involved in the alleged conspiracy accountable.
“He was the legal power behind the concept and brought it to the forefront of the Trump campaign.”
Known by his schoolmates as “the Cheese”, in a nod to the number-one cheesemaking state of Wisconsin where he grew up, Chesebro graduated from Harvard law in 1986. There he associated with a group of students clustered around the venerated liberal constitutional law professor Laurence Tribe.
Several of the group went on to have distinguished careers of their own – including Toobin, the US supreme court justice Elena Kagan and Ron Klain, Biden’s first White House chief of staff.
Tribe told the Guardian that Chesebro worked for him as a research assistant and was “obviously bright and seemingly decent”. Tribe’s experience of him as a capable legal scholar deepens the mystery surrounding his current predicament.
“He’s smart enough to know full well that the scheme he helped to cook up – a conspiracy for fake electors to gather and sign phony pro-Trump ballots – was manifestly criminal.”
After college Chesebro set up his own law firm in Cambridge, Massachusetts, where he displayed largely liberal leanings. He helped Tribe fight on behalf of the 2000 Democratic presidential candidate Al Gore in the supreme court blockbuster Bush v Gore, donated his money exclusively to Democratic candidates, and expressed glowing approval of the rising star of the party, Barack Obama.
The cases he took on also had a clear liberal bent. He represented plaintiffs suing big corporations, including Vietnam veterans taking on chemical companies, and acted as deputy special counsel in the Iran-Contra investigation into the Reagan administration’s secret sale of arms to Iran.
Had the clock stopped there, Chesebro’s career might have been summed up as successful yet unexceptional. But around 2014 his life took a startling turn.
He invested in bitcoin and appears to have struck gold, telling Tribe that he made several million dollars. New-found wealth coincided with a dramatic volte-face in his political affiliations.
By 2016 he was working on a case challenging birthright citizenship with John Eastman, the rightwing constitutional lawyer who was also indicted in Georgia this week. In 2018, Chesebro represented the hard-right Republican senators Ted Cruz and Mike Lee in a voting rights case.
His political donations also did a U-turn, swinging to Trump favourites such as JD Vance in Ohio and Ron Johnson in Wisconsin.
Why Chesebro’s bitcoin bonanza should have transformed him from a liberal into a radical conservative is one of the great unanswered puzzles of this story. The consequences of the shift were clear, though, as it brought him into the orbit of Trump campaign lawyers who were on the lookout for legal back-up as they sought to counter defeat in the 2020 election.
Six days after the election, Chesebro was contacted by James Troupis, a former judge in Wisconsin with whom he’d worked on the Cruz-Lee case. Troupis was Trump’s main campaign lawyer in the state.
In his deposition to the January 6 investigation into the insurrection at the US Capitol, Chesebro described Troupis as “a friend” who wanted help challenging the Wisconsin recount. Trump had lost Wisconsin by some 20,000 votes, but his campaign was contesting the result by making unfounded claims of fraud.
When investigators asked Chesebro for details of his work with Troupis, he pleaded his fifth amendment right to remain silent. As a result we don’t know why he did it what he did next.
On 18 November he emailed his first memo to Troupis under the portentous title: “The Real Deadline for Settling a State’s Electoral Votes”. The document is likely to enter the annals of US history as one of the earliest attempts to sketch out the fake elector plot.
In the words of the federal judge David Carter, the idea was in essence “a coup in search of a legal theory”.
The Electoral Count Act sets a calendar for deciding presidential elections. It stipulates 8 December as the “safe harbor” deadline for states to certify their results, which Congress must then honour. On 14 December, electors – individuals nominated by the party that has won the election in each state – gather in state capitols to cast their votes and send them to Washington.
Chesebro’s memo ran roughshod over this established procedure in two significant ways. First, it proposed that Trump’s electors should meet at the Wisconsin capitol on 14 December to cast their votes even though he had lost the state.
Second, the Chesebro memo argued that the key date in the election calendar was in fact 6 January. That was the day when a joint session of Congress would rubber stamp the votes cast in each state and formally declare the winner.
Established constitutional law dictates that 6 January is largely ceremonial, but Chesebro’s memo dismissed that. It argued that the law could be disregarded and that the losing candidate – Trump – could continue to challenge the results of the election all the way to 6 January.
When Tribe read the memo prepared by the person he had mentored at Harvard, he was astonished. By blatantly ignoring the law and calling for fake votes to be sent to Congress, Chesebro had in Tribe’s opinion effectively called for state and federal crimes to be committed.
To add insult to injury, Tribe recounts in a Just Security article that in his memo Chesebro even misrepresented Tribe’s own work. “As a result of this misrepresentation, Chesebro put me in the (outlandish) camp of those suggesting that the Electoral Count Act can be disregarded.”
Chesebro went on to draft two other significant memos and send them to Troupis, on 6 December and 9 December 2020. In them he took his initial theory and pushed it further into the legal wilderness.
Read together, the 6 and 9 December memos expand the fake elector plot both geographically and in the lawlessness of its ambition. Now the plot would take place not just in Wisconsin, but in six states – Wisconsin plus Arizona, Georgia, Michigan, Nevada and Pennsylvania – all of which Trump had lost (a seventh state, New Mexico, was added later).
Pence would then cast off his time-honoured ceremonial role on 6 January and instead unilaterally block Biden’s victory.
Chesebro himself was at the Capitol grounds on 6 January 2021. A CNN investigation identified him tagging along after the conspiracy theorist Alex Jones. He was the only member of Trump’s legal team known to have been present that day, though there is no evidence he entered the Capitol building or engaged in violence.
As Smith puts it in his federal indictment of Trump, Chesebro’s memos had “evolved over time”. They now proposed “a corrupt plan to subvert the federal government function by stopping Biden electors’ votes from being counted and certified”.
The Guardian asked Chesebro through his lawyer to respond to claims that his memos laid out an extreme legal theory that attempted to justify an effective coup, but he did not immediately respond. The Washington Post reported he has taken refuge in Puerto Rico and is keeping a very low profile, even for him.
Chesebro’s own memos suggest that he knew his proposal was irregular. “I recognize that what I suggest is a bold, controversial strategy,” he wrote on 6 December.
Smith’s federal indictment also contains a telling anecdote from 11 December 2020 in which Chesebro discussed the need to petition the supreme court to provide cover for the fake electors. Without such cover, he said, the casting of fake votes “could appear treasonous”.
Chesebro now finds himself in deep legal and professional trouble. On top of the Georgia charges, he is facing an ethics investigation in New York, prompted by separate complaints from the 65 Project and from numerous prominent lawyers including Tribe who have called for him to be disbarred.
It all speaks to the question that hangs over this elusive figure: why? Why would such an accomplished lawyer with a liberal past endanger reputation and career to chase what, at its most charitable, could be described as a legal fantasy?
It was not for lack of knowledge, Teter suggested. “He had the legal training and the ability to discern that what he was suggesting was an illegal pressure campaign at best, and a direct violation of the Electoral Count Act.”
Nor for money. Chesebro told the January 6 investigation that he did his Trump work pro bono (and this week we learned that other Trump lawyers including Rudy Giuliani have never been paid).
Toobin wonders whether Chesebro got carried away by the gamesmanship of it all. “What’s so troubling about the memos is that there was absolutely no recognition that an election had taken place and Biden had won. They read as though he is coming up with strategies to win a video game.”
Tribe has also scratched his head over the metamorphosis of his former student. “What might account for someone as obviously bright and seemingly decent as Ken Chesebro to flip?” he asked.
Invited to answer his own question, Tribe replied: “To be truthful, I have no earthly idea. It genuinely baffles me.”
