Opinion: Why the Kenneth Chesebro and Sidney Powell guilty pleas are so dire for Donald Trump

Kenneth Chesebro in court in Atlanta
Kenneth Chesebro accepted a plea deal in Atlanta last week.
(Alyssa Pointer / Associated Press)

On Friday, lawyer Kenneth Chesebro pleaded guilty to a felony charge for conspiring to overturn the 2020 election results in Georgia. In the plea deal, he agreed to testify against his co-conspirators in the racketeering case brought by Georgia prosecutors against former President Trump and others.

Chesebro’s guilty plea — and Trump lawyer Sidney Powell’s guilty plea to six misdemeanor counts in the same case on Thursday — are extremely valuable to Fulton County Dist. Atty. Fani Willis’ prosecution. Their agreement to provide evidence against other defendants is a significant blow to Trump and other top figures in the case, including Rudy Giuliani, former White House Chief of Staff Mark Meadows and California lawyer John Eastman.

The two pleas show Willis’ strategy is unfolding precisely as designed — working up the ladder with testimony from the lesser participants to the top defendants in the alleged conspiracy.


Fulton County Dist. Atty. Fani Willis also charged 18 others, including Rudy Giuliani and John Eastman, taking advantage of the state’s broad RICO statute.

Aug. 15, 2023

According to CNN, Chesebro has now “implicated Trump in a criminal conspiracy” and established, as part of the plea, that the fake electors plot was part of “‘an attempt … to violate’ the US Constitution and federal law, by subverting the Electoral College proceedings.”

Chesebro was the first person to plead to a felony. Other defendants will surely see the ominous trend — with each plea, Willis is demanding admission to crimes of increasing severity. Those remaining defendants (other than Trump) should be thinking even more seriously about getting a plea deal before the cost gets any higher.

The plea deals for Chesebro and Powell matter for two main reasons. First, both lawyers stood on high rungs of the ladder, very close to the top. Second, avoiding a trial for either is a win for Willis.

If Willis is focused on trying Trump and his top lieutenants, she would not want a trial previewing her evidence so that other defendants could see whatever weak links there may be in the prosecutors’ evidentiary chain.

What makes Powell and Chesebro so important?

Fulton County Dist. Atty. Fani Willis’ prosecution will remain in state court. The former president probably made a crass calculation about the judges.

Oct. 2, 2023

Powell has firsthand testimony to give about Giuliani. Recall that she appeared with him at the infamous November 2020 press conference at which brown hair dye appeared to be dripping down from Giuliani’s sideburns. Powell spewed debunked conspiracy theories about Dominion election machines switching Trump votes to Biden.

More significantly, she attended, with Giuliani, Meadows and Michael Flynn, Trump’s former national security advisor, the shouting-match meeting in the Oval Office on Dec. 18, 2020, in which seizing voting machines and other “outrageous suggestions about overturning the election” were “a central focus.”


What else was discussed that Powell can testify to? Notably, shortly after the meeting, Trump tweeted his fateful shout-out to his followers: “Big protest in D.C. on January 6th,” the tweet said, “Be there, will be wild!” Willis knows exactly what Powell has to say about that meeting and everything else, since Powell had recorded a pre-plea “proffer,” a sworn statement of the testimony she can provide against other conspirators.

Likewise, Chesebro’s testimony is incredibly valuable. Chesebro worked with both Eastman and Giuliani, each of whom worked intimately with Trump.

Chesebro was an alleged original architect of the false legal claim that Vice President Mike Pence had the authority to overturn the election by rejecting or delaying Congress’ Jan. 6 election certification vote.

In December 2020 and January 2021, the Georgia indictment states, Chesebro and Eastman exchanged emails with edited drafts of one or both memos that Eastman sent to Trump laying out the unlawful scheme. The indictment also alleges that the two talked together and agreed about tactics for executing the plot.

Significantly, Chesebro appears to have been deeply involved in its execution. Giuliani had apparently deputized Chesebro to “run point” in reaching out to fake electors such as Nevada’s Jim DeGraffenreid.

In addition, the indictment cites an instance in which Chesebro met in person with a fake elector while Giuliani was on the phone. Chesebro is sure to have significant testimony about a conversation with Giuliani before that meeting.

With these plea deals, Chesebro and Powell seem destined to testify against Trump, and the odds that Eastman and Giuliani plead skyrocket. If that happens, Trump’s prospects of escaping a conviction could dim considerably.


There’s another form of accountability awaiting Chesebro in California. Like Eastman, who is currently facing disbarment in a State Bar trial, Chesebro is a member of the California Bar. He, too, will almost certainly face disbarment proceedings.

California lawyers can be disbarred for crimes involving dishonesty. Chesebro just confessed to conspiring to submit false documents in a scheme to overturn the Constitution. And as an attorney, he took an oath to uphold the U.S. Constitution and the California Constitution.

His plea on Friday was very bad news for his future. But along with Powell’s plea, it is even worse news for Giuliani, Eastman and Trump.

Dennis Aftergut is a former federal prosecutor in San Francisco and currently of counsel to Lawyers Defending American Democracy.