MAGA lawyers take a sweetheart deal for democracy. Trump should be frightened

Why the Kenneth Chesebro and Sidney Powell plea deals matter

Published October 21, 2023 8:00AM (EDT)

Kenneth Chesebro and Sidney Powell (Photo illustration by Salon/Getty Images)
Kenneth Chesebro and Sidney Powell (Photo illustration by Salon/Getty Images)

Within 24 hours this week, two of the lawyers most closely identified with Donald Trump’s attack on the 2020 election officially jumped off the MAGA train.

On Friday, Kenneth Chesebro pled guilty in a Georgia courtroom. The plea is momentous because Chesebro was the main architect of Donald Trump's “coup in search of a legal theory,” as a federal judge has called Trump’s attempt to overturn the results of the 2020 election. Chesebro’s admission of guilt and promise of cooperation send a stark message to Trump: the erroneous legal theory central to his coming prosecutions was part of a criminal scheme. Taken with Sidney Powell’s surprise guilty plea the day before, this means two of the main actors in the 2020 election conspiracy have just become witnesses against Trump, who now faces an enhanced prospect of conviction as a result. 

Though Chesebro kept a lower profile than Trump’s other collaborators, he provided the legal bedrock of the coup attempt. Chesebro began his involvement in the 2020 election scheme in Wisconsin, where he provided the Trump campaign’s attorney there with legal advice in recount litigation. After those measures failed, Chesebro zeroed in on the presidential electors. While another of Trump’s outside lawyers, John Eastman, has become the face of the “alternate electors” dimension of the overarching scheme, Eastman’s ideas were in fact originally developed by Chesebro. He contended that the presiding officer in Congress on Jan 6 - either the vice president or, if Pence were to step aside, the President pro tempore of the Senate, could refuse to count legitimate and certified electoral votes with the goal of perpetuating Trump as president.

That theory might seem far-fetched, but Chesebro — and Trump by extension — appeared poised to defend it — until Chesebro pled guilty. His court filings suggested that he planned to rely on a dispute in Hawaii during the presidential election of 1960 to establish a precedent and justify his conduct. In that case, electors for the dueling candidates both provided certificates to Congress. Richard Nixon, the Republican candidate but also the vice president at the time, chose between them as the presiding Senate officer. 

But Chesebro distorted the Hawaii example, and with his plea it is now an even more unsustainable defense for Trump. That is because Hawaii’s 1960 election was an exceedingly close race decided by fewer than 200 votes. In 2020, however, there was no real question about the outcome when the Electoral College met on December 14: Joe Biden’s margin in the closest state—Georgia—was more than 11,000 votes. Moreover, there was good-faith post-election litigation in Hawaii as of December 14, 1960, whereas in 2020 the litigation was frivolous or already concluded. Finally, in Hawaii the then-governor issued a certificate for the alternate slate when Kennedy moved ahead in the recount. In 2020, the alternate slates had no such official certification. Taken together with the relevant law, it is painfully clear that the vice president does not have the unilateral power to use defective electoral certificates to crown an election’s loser as its winner.  

The problem for Trump is that Chesebro has just in effect turned into a witness against that theory—and thus against Trump. The former president was already in trouble because his White House Counsel Pat Cipollone, his deputy Pat Philbin, their senior colleague Eric Herschmann, the acting attorney general and his deputies, and Trump campaign lawyers had all rejected the theory. Now the principal proponent of that theory may also testify that it was baloney. That is ominous for Trump in the Georgia case, where Chesebro has pledged to appear.

But it is also likely damaging in the federal case against Trump. That is because federal prosecutors have named Chesebro as an unindicted co-conspirator, and today’s state plea deal means a federal one is more likely. Even if Chesebro refuses to cooperate with federal prosecutors, they can utilize his agreement in Georgia and his statements on the record on Friday to help establish Trump’s culpability. 

Chesebro’s lawyer reportedly stated on Friday that Trump should not fear what Chesebro had to say. But that is likely more a reflection of Chesebro’s own fear of offending the former president. There is no universe in which the chief architect of the legal theory that Trump relied upon pleading guilty in connection with that theory is good for the former president. Quite the opposite. 

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Trump’s lawyers may try to cross-examine Chesebro, but they will have a difficult time doing so because his testimony is bolstered by his own words. For example, in recently published emails, Chesebro in December 2020 admitted that his gambit had less than a “1 percent” chance of success but that his machinations could offer a “political payoff” that would push the American people to “come away from this believing that the election in Wisconsin was likely rigged, and stolen by Biden and [Kamala] Harris, who were not legitimately elected.” Earlier in the post-election period, he called his strategy "dicey," conceded that "we will probably lose," and cast other aspersions on his own theories, which shifted over time and drifted further from the law with each iteration. 

For his part, Trump has already indicated that he will advance an “advice of counsel” defense in the D.C. case and surely in Georgia as well. But that defense pivots in part on the validity of Chesebro’s legal theory, meaning the plea will significantly hamper Trump here as well. 

Then there is the one-two punch represented by Sidney Powell’s guilty plea that will also harm Trump in the state and federal cases. For starters, Trump was alleged to have committed the same overt act in furtherance of the RICO conspiracy as Powell: Act 90, the infamous December 18, 2020 Oval Office meeting once referred to as “the craziest meeting of the Trump presidency.” In it, Trump, Powell, Giuliani and others “discussed certain strategies and theories intended to influence the outcome of the presidential election, including seizing voting equipment and appointing Powell as special counsel with broad authority to investigate allegations of voter fraud in Georgia and elsewhere.” Her testimony regarding this overt act will help prove Trump’s involvement in the conspiracy.   

And beyond that, Powell’s admission to her participation in the Coffee County voting machine breach, which is the focus of 10 of the 12 overt acts in furtherance of the conspiracy alleged against her, will bolster the RICO charge against Trump and all other 17 defendants by helping to demonstrate the requisite elements of a RICO crime, which boil down to two things: showings of the existence of an “enterprise” and of a “pattern of racketeering activity.” That just got a whole lot easier for the DA to prove.  

That’s not to mention the impact of the Powell plea on the federal Jan. 6 case, where she has been identified as unindicted co-conspirator 3 in the special counsel’s indictment against Trump for the same scheme nationally. Now that she’s pleaded guilty to charges for her conduct in Georgia and agreed to testify against Trump and others there, little stands in the way of her agreeing to do the same in the special counsel’s prosecution of Trump to avoid possible federal charges in that prosecution. Whatever she does in that regard, federal prosecutors have a variety of ways to utilize evidence and testimony from Powell given in the Georgia courtroom.  

Of course, all of that does not mean that Trump will fail to put up a fight in the state case or the federal one. But his defense stood on the factual proposition that he had actually won the 2020 election, and that he therefore had a legal right to press his vice president to use these “alternate” and false electoral certificates to refuse to recognize Joseph R. Biden as the winner of the election in the January 6 meeting of Congress. With the plea of Powell on Thursday, the first leg has wobbled under Trump, and with Chesebro’s plea on Friday, Trump can no longer rest on the second.

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These plea deals raise another prospect that is quite negative for Trump and the remaining defendants in the Georgia case: the pleas open up the judge’s trial calendar for the next five months, potentially allowing him to schedule the trials of others in that window, including possibly the former president. The first Trump trial on these issues in federal court is not set until March. If Chesebro and Powell could get ready for trial on an accelerated basis, surely it’s not unreasonable for Trump and other possible defendants to prepare themselves to face a jury in Atlanta at some point in the coming months. 

The impact of the pleas will not only be legal but political as well. The twin admissions by Chesebro and Powell will now color the looming GOP presidential primary. That matters because the D.C. case will not be resolved until the primaries are over. Substantial polling suggests that Republican and even more so independent voters would waver on Trump if he were convicted. Because Trump's defense has been undermined by this week’s pair of pleas, these developments allow voters and opposing primary candidates to more directly consider the hypothetical of Trump’s guilt. 

Beyond those near-term legal and political ramifications, the pleas bear on a more fundamental issue for our democracy: whether lawyers and their candidate clients can breach the law to attack election outcomes. An acquittal would have threatened our elections and the rule of law in 2024. Indeed, the playbook employed by Trump, Chesebro, and Powell was deployed in the 2022 midterms in Arizona, Nevada, Michigan, and beyond. While ultimately unsuccessful, their strategy created substantial litigation ferment and offered a preview of what might ensue in the coming election cycle.

Conversely, Chesebro’s and Powell’s guilty pleas have just sent a warning to lawyers and their candidate clients—above all Trump—not to engage in these kinds of criminal behaviors. With the 2024 election looming, that sends a positive and badly needed message about the rule of law and accountability. That is good news for our democracy, and very bad news, indeed, for Trump and his ilk.

By Norman Eisen

Norman Eisen served as White House ethics czar and ambassador to the Czech Republic under President Barack Obama, then as special counsel to the House Judiciary Committee in 2019–20, including during the first impeachment and trial of President Donald Trump.

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By Joshua Kolb

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