Kenneth Chesebro Chose the Dark Side

Kenneth Chesebro’s mug shot. Source: Fulton County Sheriff’s Office

When I initially set out to write what seemed like a dull, technical analysis of a motion by one of the defendants in the Georgia state RICO case, I couldn’t predict how often I would find myself instead shaking my head, saying “what?!” aloud, and musing about how all this would really make an incredible screenplay.

Kenneth Chesebro is no household name, but he might soon become one. Alone among the Georgia RICO conspiracy defendants, he has raised his hand high and demanded what is known as a “speedy trial” under Georgia state law. That means a trial that occurs no later than the end of the next jury term. And that in turn meant no later than November 3rd of this year. Such a compressed trial schedule, many posited, could put District Attorney Fani Willis on the ropes, giving her little time to prepare for such a massive, sprawling case.

Willis responded by one-upping Chesebro and asking for a trial date of October 23, 2023, for all defendants. I’m ready, her motion signaled. Bring it. A little more than two hours later, Judge McAfee set that date in the calendar—but for Chesebro alone at this time. The judge built backward from that day to create a schedule for discovery and motions. While the world cheered Willis’s move, she really had very little choice but to agree to the timetable demanded. Under Georgia law, as Kyle Cheney of Politico pointed out, failure to commence a trial after a speedy trial demand by a defendant would lead to discharge and acquittal of Chesebro on all charges.

It’s so far unclear, however, whether other defendants will want to come along for such a short court ride. Certainly not Donald Trump, who has already moved to sever his case from Chesebro’s and plans to do so in response to any defendant who seeks speedy resolution. It’s also unclear whether, on balance, the prosecution or the defense will benefit more from such a hurried-up schedule. 

But the main question I have after seeing these requests and motions fly is this: What exactly is Chesebro up to? Why get out in front of every other defendant like this, potentially becoming the object of intense scrutiny?

What is driving Chesebro to break with the pack?

To get a better handle on this new development, I set out to learn more about who Chesebro really is. After all, in the public January 6 hearings last year over the conspiracy to overturn the election, Chesebro’s name didn’t come up that often. He was much more behind-the-scenes, advising, orchestrating and helping to execute a devious and illegal plan for Trump to hold on to power. As such, there have been few reports about him, and he certainly garnered far less attention than the other co-conspirators such as attorneys John Eastman and Jeffrey Clark.

That changed dramatically after Jack Smith’s indictment, where Chesebro was quickly identified as “Co-Conspirator 5”—the prime architect of the fake elector scheme. Then came the Georgia RICO indictment, where he was named as a co-defendant with the man he helped try to illegally keep in the Oval Office.

And now, in a daring but possibly foolhardy bid, Chesebro has grabbed the spotlight, and he may find its glare harsh indeed. Before we jump into his role in the January 6 plot and his possible motives for wanting to go first, let’s lift the rock and peer under it to see what Chesebro’s past reveals. 

You’ll see what I mean about an incredible screenplay. In fact, it feels rather Star Wars-ian in its sweep, so I’m going with that.

The Anakin Skywalker days

Legal author Jeffrey Toobin wrote a long expose on Chesebro, known around Harvard Law School as “The Cheese.” (His name is pronounced “chez-bro” but I can’t unhear “The Cheese” since he’s from Wisconsin.) Toobin’s account paints a fascinating picture of a shy, awkward and nerdy fellow, super smart and aggressive in his legal thinking, who also exhibited some worrisome, anti-social traits. Here’s a revealing moment:

“I will never forget what happened once in the typing room,” one former fellow student recalled. (In those days, students could choose to write their exams by hand in blue books or type them in a separate room on their Smith Coronas.) “First, Ken shows up with two typewriters—one and a backup—which I had never seen before,” the student went on. “Then, with about 15 minutes left in the exam, a woman starts panicking because her typewriter has broken. She notices that Ken has two, and she asks him to borrow one for the last few minutes. He says no and tells her, ‘Harvard Law School is a dog-eat-dog place.’”

Chesebro also was one of those guys who, like Forrest Gump, winds up being in all the right—or sometimes wrong—places. He became a research assistant to Professor Laurence Tribe, the renowned constitutional law scholar who is now among those leading the charge to disqualify Trump from eligibility to run for federal office. Other student assistants in “Tribe World” included Justice Elena Kagan, former White House Chief of Staff Ron Klain, and Jeffrey Toobin himself, which is how he knew Chesebro. Later on, I’ll describe other circumstances and often insane situations where Chesebro played a role, leading to my frequent “what?!” outbursts.

Tribe, who I suppose is Obi-wan in this analogy, described Chesebro as “eager to please.” Others who worked with him said Chesebro was “fascinated with ideas and arguments, and if it’s something novel, he liked it better.” But Chesebro was aggressive to a fault, and Tribe had to rein him in at times. “I’m somewhat adventurous in the way I connect things, but Ken would often go too far out for me. There was a lack of judgment.”

Rather than take a big corporate or government job, Chesebro became a solo practitioner and stayed that way for decades since. His first client was Tribe, helping him with his law review articles and working alongside (checks notes) another research assistant named Barack Obama. (In 2004, Tribe invited Chesebro to an Obama fundraiser, and Chesebro gushed about how Obama made a great keynote speech at the convention and would make a great Supreme Court justice. He donated $500 to Obama’s campaign, along with a donation to his home state senator, the uber-progressive Democrat, Russ Feingold. Chesebro’s later actions would win up embroiling Feingold’s successor, Sen. Ron Johnson, in controversy over January 6. See? Forrest Gump!)

Chesebro’s personal life seemed outwardly stable and successful. He was married to a physician turned lawyer named Emily Stevens, and they lived modestly in an apartment across from the Harvard campus in Cambridge, Massachusetts. He spent his days doing research for Tribe, to whom he seemed as devoted as he was to his wife. Tribe had even attended their wedding in Bermuda in 1994.

In 2000, Gump—I mean Chesebro—found himself in the thick of his first national electoral crisis. He was assisting Tribe who was representing Al Gore in that election. In a chilling premonition, Chesebro wrote a long memo strategizing about how Gore might win when the electoral votes were finally counted. It would not be the last presidential election memo he would come to write.

The Dark Side swallows Chesebro

Given this picture, it is hard to see how that guy became Co-Conspirator 5, working for the Trump Campaign for free and lending his considerable legal and mental powers to the overthrow of our democracy.

It seems to start, as many bad things do, with crypto.

The lure of money and what it could bring appear to lie at the heart of Chesebro’s transformation. This passage in Toobin’s piece, describing correspondence from Chesebro to Tribe, was quite revealing:

“In January 2014, I invested in Bitcoin on the conservative assumption that there was an 80 percent chance I’d lose everything, but a 20% chance that my Bitcoin shares would rise 10 fold within a decade,” he wrote in a later e-mail to Tribe, “so that on a risk-adjusted basis, I’d expect to double my money in ten years. As things turned out, my investment multiplied 20 fold by the time I sold just four years later.” (Chesebro sent Tribe several e-mails encouraging him to invest with him in Grayscale, a crypto-investment house. “I can personally vouch for the Grayscale people, having been lucky/smart enough to make several million dollars.” Tribe passed.)

Around the same time, Chesebro separated from his wife (after more than 20 years), moved into the Ritz Carlson Residences in Boston, then later to New York to a penthouse on Central Park South. He began courting a young woman, buying her trips around the world, including a celebration of her 21st birthday in Paris and London. They apparently have since married, according to a family friend. This is quite the mid-life crisis.

His personal life wasn’t all that changed radically. His politics also morphed, taking a hard turn to the right. He began working with John Eastman, known today as Co-Conspirator 2 and co-defendant in the Georgia RICO conspiracy case. His clients also comprised some of the most deplorable clowns in the GOP, including Sens. Ted Cruz (R-TX) and Mike Lee (R-UT). Chesebro co-authored an amicus brief in a case against voting rights with James Troupis, a former Wisconsin judge who led the state gerrymander efforts in the 2010s and a decade later would lead the Trump Campaign challenges to the election in Wisconsin in 2020. Troupis was the one who brought Chesebro in to help with the election battles that year in their home state. Public records show Chesebro, after become a crypto millionaire, made large donations to Republican candidates, including to J.D. Vance (R-OH) and Ron Johnson (R-WI).

Lord Vader emerges

At some point, the man who was once a legal Jedi-in-training instead became a MAGA Sith Lord. In fairness Ken Chesebro was perhaps more like Rick Moranis in Spaceballs.

Photo courtesy of Moviestore/REX/Shutterstock

Chesebro put his election experience in 2000 and all that he had learned from Tribe over the years to work beginning in November of 2020, as the Trump campaign sought to undo the election. The focus was on the swing states, and Chesebro was in one of the swingiest: Wisconsin. 

He wrote a memo on November 18 arguing that, even though the state had gone to Biden, the electors who were pledged to Trump could meet anyway and serve as an insurance policy while the parties battled it out in court. That way, Wisconsin could present an alternate slate if the court cases came out their way. Their bases would be covered, legally speaking.

While that’s certainly unorthodox, it wasn’t illegal, at least as conceived initially. But Chesebro needed to press further, when it became clear that the courts would not rule their way. He began advocating that the alternate slates in the swing states be used to prevent Biden from achieving 270 electoral votes, rather than to act as a backstop for any court decisions. That was where his scheme crossed into illegal territory.

By December 6, Chesebro had spelled out the illegal conspiracy in another memo. The Trump electors would meet on December 14, “even if Trump has not managed by then to obtain court decisions (or state legislative resolutions) invalidating enough results to push Biden below 270.” Then Pence, as the Senate president, would recognize the Trump electors as genuine, even though “the Supreme Court would likely end up ruling” that he had no right to do so.

In another email dated December 24, 2020 Chesebro suggested to Eastman that the prospect of “wild chaos” on January 6 could lead the Supreme Court to take up a case out of his state. The Trump Campaign was actively trying to decide whether to file papers that could prompt at least four justices to hear the election challenge out of Wisconsin.

In the end, Tribe was right about Chesebro. He was always willing to go too far. And he definitely lacked judgment. Combine that with his shift to extremist politics, and Chesebro became a useful and dangerous tool for the coup plotters.

Rewriting the narrative

As far as I’m aware, Chesebro has only given one interview about his work on the Trump campaign since January 6, 2021. That was to Talking Points Memo, which published the piece in June of 2022. In it, Chesebro tried hard to present himself as someone solely interested in the academic, legal arguments he had raised. He implied that he had joined the Trump Campaign because he believed that it was having trouble getting good representation. And he clung to the idea that he had done nothing wrong, because he was merely “identifying possible strategic options that might come into play” and “this is what lawyers do.”

“There was good reason to argue that under Article II, that Biden had not legitimately won the electoral votes,” Chesebro told the interviewer. “I’m not saying that Trump deserved to win in each state, I’m saying it was legitimate to argue under Article II that there was a problem.”

Chesebro also claimed that he “abhorred” the violence at the Capitol as self-defeating. He described it as “primarily a human disaster” and said that “it was the worst possible thing that could have happened in terms of lawyers that had serious concerns about the election in several states, that were never really addressed on the merits.”

From this interview, you’d think Chesebro was still locked in his tower somewhere, his words no more than “advice” that his clients could use if they so wished. You’d think the last place Chesebro would be, then, is in the thick of the violence that day.

A bombshell report on Chesebro’s whereabouts on January 6

If Chesebro were just a nerdy lawyer with unorthodox views about the powers of the Vice President and the use of fake electors, then why was he on the Capitol grounds on January 6, following the wacko conspiracy peddler Alex Jones around and filming him the whole time?

Come again?

A week or so ago, CNN dropped this bombshell:

When conspiracy theorist Alex Jones marched his way to the US Capitol on January 6, 2021, riling up his legion of supporters, an unassuming middle-aged man in a red “Trump 2020” hat conspicuously tagged along.

Videos and photographs reviewed by CNN show the man dutifully recording Jones with his phone as the bombastic media personality ascended to the restricted area of the Capitol grounds where mobs of then-President Donald Trump’s supporters eventually broke in.

While the man’s actions outside the Capitol that day have drawn little scrutiny, his alleged connections to a plot to overthrow the 2020 election have recently come into sharp focus: He is attorney Kenneth Chesebro, the alleged architect of the scheme to subvert the 2020 Electoral College process by using fake GOP electors in multiple states.

This was a record scratch moment for me. I thought he “abhorred” the violence and believed it was “the worst possible thing” to happen to those serious lawyers who had serious and legitimate concerns. Isn’t that what he’d claimed?

But he was there, in a MAGA hat, on the Capitol grounds, filming Alex Jones.

Suffice it to say, we should trust none of the careful narrative that Chesebro has spun. At some point, he became radicalized and a true believer, and apparently even a supporter of the insurrection, though there’s no evidence he entered the building. He could be charged, as Jones’s co-host Owen Shroyer was, with the federal version of trespass. And we all need to know how exactly he was connected in the first place with Alex Jones. It is worth noting that Jones may have helped coordinate violent attacks on the Capitol itself if a play-by-play by Capitol Hunters of his role in signaling other insurrectionists proves correct.

Back to that motion for a speedy trial

Now that it’s pretty clear Chesebro was not only the architect of the fake elector scheme but also an active participant and associated with known, extremist elements, we need to look at the motion for a speedy trial with this in mind.

There is much that we don’t yet know about Chesebro, including what he was doing at the Capitol with Alex Jones that day. Did they communicate? Was he apprised of the violence ahead of time? Who else was involved?

The CNN report on Chesebro’s whereabouts and connection to Jones is only a week old. Investigators likely haven’t even begun to dig into this sufficiently. But given time, they might learn many more things about Chesebro.

So if you’re Chesebro, why not raise your hand now, get the full attention of prosecutors among all the 19 defendants, and maybe work out a deal, especially now that you know from the indictments what they have and don’t yet have? Such a deal might overlap considerably with what you’re willing to tell Jack Smith in exchange for leniency.

It’s important to be the first one out of a pot that’s starting to boil.

Now, sure, it’s possible that Chesebro has deluded himself into thinking that he is innocent and just a lowly attorney providing a few legal options to the president. And he may simply want a trial over and done with because he’s convinced of his own innocence. But any objective look reveals that we’re way past that point.

As legal expert Ryan Goodman noted, Chesebro’s fingerprints are all over the scheme with the fake electors, which Chesebro admitted in emails he was to “coordinate” and “help with the logistics.” He admits also to drafting the fake elector certificates based on the real 2016 ones. And as Goodman also pointed out, one federal judge looking at the facts in the Eastman privilege dispute already concluded that a Chesebro memo “likely furthered the crimes” in the case. 

And in case anyone was wondering, Chesebro himself exhibited consciousness of guilt. As The Guardian observed,

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.”

What happens now?

The other defendants in the case now have a choice to make. Do any of them join Chesebro and essentially go to trial right away? There may be others who would prefer not to be lumped together with the likes of Sidney Powell and Rudy Giuliani, let alone the ex-president, in a vast conspiracy to overturn the election. As mere foot soldiers in this plan, they might prefer to go first and point the finger at others who were more culpable.

Many of these defendants were electors who agreed to sign false documents at the urging of the Trump campaign. They would be the first to throw members of that campaign, including Chesebro, under the bus as the real brains and muscle behind the effort. Some of them are seeking removal to federal court precisely on these grounds: that they only became defendants because they were following the advice of a federal official (Trump) and his lawyers.

Still, October 23, 2023 is mighty soon. Some might ask to join Chesebro but request the trial date be pushed back so that their lawyers have more time to review what will certainly be voluminous discovery turned over by Willis’s office. 

Chesebro is undoubtedly aware of this possibility, and if he’s as intelligent and strategic as he was in crafting those election challenge plans, he also knows that the early trial date might not and indeed likely will not hold, especially with so many competing interests at play. Still, my guess is that Chesebro thinks it’s his best chance to press ahead and perhaps strike a plea deal before further investigation reveals more problematic evidence of criminality.

But he is still just one smart guy against two formidable, seasoned prosecutors and their teams. Everyone knows Chesebro has valuable information and evidence against others in the conspiracy. The only question now is how much he could trade for it and when, and whether he can escape the full and terrible consequences of having embraced and pledged fealty to Emperor Trump.