Back-to-back plea deals pose grave legal threat to Donald Trump

Oct 21, 2023, 3:43 PM

Sydney Powell, Donald Trump and Kenneth Chesebro are pictured in a split image. Two stalwart allies...

Sydney Powell, Donald Trump and Kenneth Chesebro are pictured in a split image. Two stalwart allies of former President Donald Trump flipped against him in the past 36 hours, a staggering turn of events that could now pose a grave threat to his ability to fend off criminal charges related to his efforts to overturn the 2020 presidential election. Photo credit: Getty images.

(CNN) — Two stalwart allies of former President Donald Trump flipped against him this week, a staggering turn of events that could now pose a grave threat to his ability to fend off criminal charges related to his efforts to overturn the 2020 presidential election.

The rapid-fire developments are a massive boost for prosecutors in Fulton County, Georgia, and the separate but overlapping federal case against Trump that was filed by Justice Department special counsel Jack Smith.

The pleas are a stark display of the reality that the Georgia case against Trump and his co-defendants is getting stronger. While Trump has vowed to fight until the bitter end, these newly inked plea deals force his co-defendants to confront the same difficult choice: cut a deal or roll the dice at trial.

For two prominent Trump co-defendants – Sidney Powell and Kenneth Chesebro – the looming five-month trial, potentially resulting in a yearslong prison sentence, appears to have spurred them into flipping.

Their decisions to transform from Trump diehards to key witness against him have likely shattered any sense of invincibility that the former president or others charged may be feeling – perhaps for the first time.

Implicating Trump

Chesebro pleaded guilty Friday to a felony conspiracy charge, admitting he worked with Trump and other members of the former president’s inner circle to overturn the 2020 election by putting forward slates of fake Republican electors in multiple states that Trump lost.

Chesebro directly implicated Trump in a criminal conspiracy, and his plea establishes for the first time that the fake electors plot was illegal. Notably, Chesebro has now admitted that “the purpose” of the fake electors conspiracy was to “disrupt and delay the joint session of Congress on January 6, 2021,” which is a key element of the federal charges Trump is facing.

As part of the plea, Chesebro established that the fake electors plot was part of “an attempt… to violate” the US Constitution and federal law, by subverting the Electoral College proceedings. This dovetails with the allegations against Trump in Smith’s federal indictment.

On Thursday, former Trump campaign lawyer Powell pleaded guilty to charges stemming from a separate, but complementary, effort to interfere with the 2020 election by breaching Georgia voting systems.

While Powell’s guilty plea only covers charges related to the breach of election equipment in Coffee County, Georgia, her deal with prosecutors opens the door for testimony about first-hand interactions with Trump and other key co-defendants.

For example, if called to the stand in a future trial, Powell could face questions about White House meetings she attended where Trump considered taking extreme steps to overturn the 2020 results, like ordering the Pentagon to seize voting machines.

Chesebro similarly agreed to cooperate fully with Fulton County investigators as part of his deal – which includes testifying against Trump and other defendants if called as a witness.

Trump is the only person charged thus far in the federal case, but both Chesebro and Powell are unindicted co-conspirators. Chesebro has now admitted conspiring with Trump in the same fake elector plot that is featured prominently in the federal case against Trump – which is set for trial in March.

No silver bullet

Steve Sadow, Trump’s lead counsel in the Georgia election subversion case, responded Friday to Chesebro’s guilty plea by suggesting it was likely motivated by the “looming threat of prison time.”

He speculated in a statement that Chesebro’s guilty plea “was the result of pressure by Fani Willis and her team, and the prosecution’s looming threat of prison time.”

Trump’s attorney also pointed out that prosecutors dismissed Chesebro’s separate racketeering charge that underpins the indictment against all 19 co-defendants, including the former president. Prosecutors have now dropped that RICO charge against all three defendants who have already taken plea deals.

But just because a onetime Trump loyalist has decided to help prosecutors go after him, that doesn’t mean the former president is doomed.

Back in 2018, Trump’s ex-lawyer Michael Cohen struck a plea deal with federal prosecutors and implicated Trump in an illegal campaign finance conspiracy – but the Justice Department never charged Trump with that alleged crime. But Cohen has cooperated with New York state investigators and is set to testify against Trump next week at Trump’s civil business fraud trial there.

Sadow brushed off the threat of possible testimony from Chesebro and Powell at Trump’s eventual trial on the Georgia election subversion charges.

“Once again, I fully expect that truthful testimony would be favorable to my defense strategy,” Sadow said.


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Back-to-back plea deals pose grave legal threat to Donald Trump