'Ominous' sign for Donald Trump? Guilty pleas from Chesebro, Powell raise the stakes in Georgia

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The latest guilty pleas from two key allies in Donald Trump's high-profile Georgia election interference case put new pressure on the former president and raise questions about whether his once-loyal associates may one day flip on him.

Two attorneys, Kenneth Chesebro and Sidney Powell, pleaded guilty to related crimes this week and agreed to testify against other defendants. They had been charged with playing separate roles in an alleged multi-pronged conspiracy to overturn the results of the 2020 presidential election. Coming after a third defendant, Scott Hall, pleaded guilty in September, their deals bolster the weapons in prosecutors' toolbox, and may pressure other defendants to flip -- a move that would raise the legal stakes for Trump.

''Once you get a couple people pleading, it starts sort of an avalanche of pleas," said Chandelle Summer, a Georgia attorney who previously worked as both a prosecutor and public defender in the state.

These handout booking photos provided by the Fulton County Sheriff's Office show the 18 co-defendants who surrendered and were booked along with former President Donald Trump after they were indicted on charges related to their efforts to overturn the 2020 US Presidential election in Georgia.
Top row (l-r): Rudolph William Louis Giuliani, John Charles Eastman,Mark Randall Meadows, Kenneth John Chesebro, Jeffrey Bossert Clark,Jenna Lynn Ellis
Middle row (l-r): Ray Stallings Smith III, Robert David Cheeley, Michael A. Roman, David James Shafer, Shawn Micah Tresher Still, Stephen Cliffgard Lee
Bottom row (l-r): Harrison William Prescott Floyd, Trevian C. Kutti, Sidney Katherine Powell, Cathleen Alston Latham, Scott Graham Hall, Misty Hampton

In addition to agreeing to testify, Chesebro, Powell, and Hall will turn over relevant documents to the state of Georgia, and are prohibited from communicating with witnesses or defendants in the case.

Norman Eisen, a Brookings Institution senior fellow who served as special counsel to the House Judiciary Committee from 2019 to 2020, said information from the three former Trump associates, could bolster the government's evidence in another pending Trump trial -- federal election meddling case, which is scheduled to start in March in Washington.

"Both Powell and Chesebro were unindicted co-conspirators in the federal case, so they're central to it," Eisen said. "It is ominous for the other defendants in the state or federal cases, above all Donald Trump."

Kenneth Chesebro provides inside account about fake electors

Chesebro, an election lawyer, pleaded guilty Friday in the Fulton County Superior Court to a felony charge of conspiracy to commit filing false documents. Chesebro offers an inside view of the development of the scheme to recruit fake presidential electors to vote for Trump in states that President Joe Biden won.

Chesebro created and distributed false documents in Georgia and other states for people to submit to the National Archives and Congress posing as presidential electors, according to Daysha Young, the executive district attorney in Fulton County.

"The defendant provided detailed instructions to co-conspirators in Georgia and other states for creating and distributing these false documents," she said.

Kenneth Chesebro, lawyer for U.S. President Donald Trump's 2020 re-election campaign, appears before Judge Scott McAfee in a case management court hearing related to the Fulton County 2020 election interference case in Atlanta on Oct. 20, 2023.
Kenneth Chesebro, lawyer for U.S. President Donald Trump's 2020 re-election campaign, appears before Judge Scott McAfee in a case management court hearing related to the Fulton County 2020 election interference case in Atlanta on Oct. 20, 2023.

Chesebro's deal gets the prosecution closer to John Eastman, who around that time appears to have been in "constant communication" with Rudy Giuliani and Donald Trump, said Melissa Redmon, a former Fulton County prosecutor who directs the University of Georgia School of Law's Prosecutorial Justice Program.

Those connections will help the state paint a picture for the jury of the false elector activity being ultimately motivated by a desire to make sure Trump retained the presidency "by any means necessary," Redmon said.

Sixteen co-defendants in the Georgia case, including Trump, Eastman and Giuliani, have pleaded not guilty.

Sidney Powell raised baseless claims of election fraud in Oval Office meeting with Trump

Powell, an election lawyer who spread baseless claims of voter fraud, pleaded guilty Thursday to a half-dozen misdemeanors associated with tampering with election equipment in Coffee County, Georgia.

Legal experts said Powell's agreement to provide testimony could have a weighty impact on the wider case because she had significant dealings with Trump, Giuliani, and others.

Former Mayor of New York Rudy Giuliani, left, listens to Sidney Powell, during a news conference at the Republican National Committee headquarters, Thursday Nov. 19, 2020, in Washington.
Former Mayor of New York Rudy Giuliani, left, listens to Sidney Powell, during a news conference at the Republican National Committee headquarters, Thursday Nov. 19, 2020, in Washington.

Powell can also describe how co-defendants tried to overturn the 2020 election. She and Giuliani attended a raucous meeting at the White House with Trump, where they discussed having the military seize voting machines. Trump never acted on the proposal.

Scott Hall chatted for an hour with co-defendant who drafted spurious DOJ letter

Hall, a bail bondsman who served as a go-between for several of the co-defendants, pleaded guilty in September to five misdemeanors dealing with interfering with election duties.

Donald Trump co-defendant, Scott Hall, pleads guilty in GA racketeering case
Donald Trump co-defendant, Scott Hall, pleads guilty in GA racketeering case

Hall helped SullivanStrickler employees tamper with the Coffee County equipment.

Hall also made multiple calls to co-defendants in the case. For example, Hall spoke with Jeffrey Clark, a former assistant attorney general, for more than an hour Jan. 2, 2021, according to the indictment.

Clark, who pleaded not guilty, is charged with drafting a letter of false statements about Justice Department concerns with the 2020 election, to be sent to Georgia officials. Acting Attorney General Jeffrey Rosen refused to sign or send the letter.

Hall also spoke repeatedly with co-defendants accused of trying to intimidate election workers to change their stories about what happened with ballot counting at State Farm Arena on election night 2020.

Georgia court calendar opens, but Trump trial date uncertain

Although the pleas open up several months on McAfee's calendar that had been reserved for Powell and Chesebro's trial, Redmon said typically in Fulton County there are several steps involving pre-trial deadlines before a trial date is set in a case, and she doesn't expect to see a trial date for Trump soon.

Summer said McAfee would have to take the schedules for Trump's other criminal trials into account, as well as his attorneys' scheduling conflicts.

"Assuming he's acquitted in the DC case, I think then they'll probably specially set a trial for sometime after that, maybe the fall of 2024," she said.

Eisen suggested McAfee might aim to hold Trump's Georgia trial sooner.

"If Chesebro and Powell could get ready for trial on an accelerated basis, surely it's not too unreasonable for Trump and possibly other defendants to prepare themselves to face a jury in Atlanta at some point in the coming months," Eisen said.

This article originally appeared on USA TODAY: Trump in new peril after Sidney Powell, Kenneth Chesebro plead guilty