Chesebro pleads guilty to Georgia election interference charges in another blow to Trump

In another potential blow to former President Donald Trump, lawyer Kenneth Chesebro becomes the third defendant in the Georgia election interference case to plead guilty and agree to testify. Trump gets more bad news in the New York financial fraud civil trial, with the judge threatening him with possible jail time for violating a gag order, then fining him $5,000.

Georgia election interference

Chesebro, like Powell, pleads guilty

Key players: Pro-Trump lawyers Kenneth Chesebro and Sidney Powell, Judge Scott McAfee, Fulton County District Attorney Fani Willis

  • With jury selection underway in Georgia, Chesebro suddenly entered a guilty plea Friday, the second defendant in as many days to do so in the sprawling Georgia election interference case brought by Willis, ABC News reported.

  • Powell accepted a plea deal with prosecutors in the alleged scheme to overturn the 2020 presidential election in the state. Notably, Chesebro agreed to testify in the trials for the other defendants, including Trump.

  • The deal, which McAfee signed off on, allows Chesebro to avoid jail time. He will serve five years’ probation and must also pay a $5,000 fine, write a letter of apology to the citizens of Georgia and perform 100 hours of community service.

  • Chesebro was charged with seven criminal counts. Prosecutors accused him of concocting an alternate elector strategy to try to contest the election results.

  • Powell and Chesebro had both requested speedy trials and had vigorously proclaimed their innocence as jury selection approached.

  • Bail bondsman Scott Hall also accepted a plea deal in the case.

Why it matters: Like Powell, Chesebro had direct contact with Trump in their efforts to overturn the election. His testimony against the former president could go a long way in undermining Trump’s defense and could serve as further incentive for other defendants to accept plea deals.

New York financial fraud

Judge threatens Trump with possible jail time, then fines him $5,000

Key players: Judge Arthur Engoron, Trump attorney Christopher Kise

  • Engoron fined Trump $5,000 on Friday for violating the gag order put in place after the former president attacked a member of the judge’s staff, the Associated Press reported.

  • Earlier in the day, Engoron tore into Trump’s lawyers for what he called a “blatant violation” of the gag order he issued in the case on Oct. 4, the Daily Beast reported.

  • “Last night I learned the offending post was never removed from a website,” Engoron said. “I made it clear failure to comply will result in serious sanctions. It remained on the Donald J. Trump campaign site and in fact it has been on there for the past 17 days [and] it was removed late last night after an email from this court.”

  • “Incendiary untruths can and have led to serious physical harm,” Engoron continued. “I will now allow the defendant to explain why this should not end up with serious sanctions or I could possibly imprison him.”

  • Kise apologized on behalf of Trump, calling the incident “unintentional.”

  • “The Truth Social post was taken down when the court asked,” Kise responded, adding that Trump “never made any more comments about court staff, but it appears no one took it down on the campaign website.”

  • Engoron has already ruled that Trump, his adult sons and their family business are liable for years of financial fraud carried out in New York. Trump has repeatedly accused the judge of being biased against him.

  • On Friday, Kise struck a more humble tone about the post that remained up on the former president’s campaign website: “It is unfortunate and I apologize on behalf of my client,” he said.

  • In issuing the fine, Engoron said in a written ruling that Trump was “way beyond the ‘warning’ stage.”

Why it matters: Engoron has the power to enforce sanctions against Trump for violating court orders. He has shown little hesitance to rule against the former president and will later decide what penalties Trump, his adult sons and their business must pay in the case.

Recommended reading

Associated Press: Trump is not above the law,’ prosecutors say in urging judge to let federal election case proceed

The Hill: Trump legal cases tracker: What’s next


Thursday, Oct. 19


Photo Illustration: Yahoo News; photos: Michael M. Santiago/Getty Images, Andrew Kelly-Pool/Getty Images, Getty Images (3).

New York officials tell Judge Arthur Engoron that the Trump Organization did not hand over documents about the size of the former president’s penthouse apartment. In Georgia, meanwhile, pro-Trump lawyer Sidney Powell becomes the second defendant to plead guilty in the plot to overturn the 2020 election in Georgia.

New York financial fraud

Prosecutors accuse Trump Organization of withholding documents about N.Y. penthouse

Key players: New York Attorney General Letitia James, senior enforcement counsel Kevin Wallace, Judge Arthur Engoron, former Trump CFO Allen Weisselberg, former Judge Barbara Jones

  • Lawyers for James wrote to Engoron Thursday accusing the Trump Organization of withholding subpoenaed documents in the case that will decide what penalties Trump, his adult sons and business must pay for years of financial fraud, Insider reported.

  • Citing missing emails sent in 2016 between the company and Forbes magazine, which publishes an annual list ranking the wealthiest Americans, Wallace asked Engoron to approve of a “forensic” review of Trump’s business records by Jones, the independent monitor appointed in the case.

  • Forbes, which left Trump off this year’s list of richest Americans, published a story last week accusing Weisselberg of lying under oath about his role in the bogus valuations of Trump’s triplex apartment in Trump Tower.

  • Though Trump’s company has turned over approximately 900,000 documents to James’s office, prosecutors say they have not met their legal obligation to fully comply with subpoenas.

  • “The failure to produce these later emails indicates a breakdown somewhere in the process of preserving, collecting, reviewing and producing documents,” Wallace wrote.

Why it matters: Forbes said the emails in its possession show that Weisselberg “played a key role” in trying to convince the magazine that Trump’s penthouse apartment “was worth more than it really was.” If Engoron directs Jones to conduct a forensic audit of those documents, it could spell more trouble for Trump and for Weisselberg.

Georgia election interference

Powell pleads guilty and agrees to testify in trials of other defendants

Key players: Pro-Trump lawyer Sidney Powell, Judge Scott McAffee, lawyer Kenneth Chesebro, bail bondsman Scott Hall, Fulton County District Attorney Fani Willis, former Trump lawyers Rudy Giuliani and Jenna Ellis

  • On the eve of the start of her trial alongside co-defendant Chesebro, Powell pleaded guilty Thursday to six misdemeanor charges, including five counts of conspiracy to commit election interference, USA Today reported.

  • As part of her plea deal, Powell agreed to testify in the future trials for an unspecified number of the other 18 people charged in Georgia. She must also pay nearly $9,000 in fines and write a letter of apology to the citizens of the state. Prosecutors will ask that she be placed on probation for six years.

  • Powell’s testimony could prove useful to prosecutors in the trials of others charged. She held a White House meeting with Trump in December of 2020, for instance, to discuss using the military to seize voting machines. She also held an infamous press conference alongside Trump lawyers Giuliani and Ellis where the trio pressed bogus allegations of voter fraud.

  • Powell is the second defendant of the 19 charged in Georgia to plead guilty. Bail bondsman Scott Hall did so in late Sept.

  • Chesebro rejected an offer of a plea deal on Thursday.

Why it matters: Prosecutors only cut plea deals with those who they think will serve as credible witnesses in other trials. While Powell floated some of the most outlandish conspiracy theories about the 2020 election of those charged, she was also a firsthand witness to the attempts to overturn Trump’s loss.

Recommended reading


Wednesday, Oct. 18


Photo Illustration: Yahoo News; photos: Brendan Smialowski/AFP via Getty Images, Samuel Corum/Getty Images, Getty Images (3).

Photo Illustration: Yahoo News; photos: Brendan Smialowski/AFP via Getty Images, Samuel Corum/Getty Images, Getty Images (3).

Lawyers for former President Donald Trump file a notice to appeal a partial gag order in the federal Jan. 6 election interference case. Trump co-defendants Sidney Powell and Kenneth Chesebro lose bids to get the criminal charges against them dismissed in the Georgia 2020 election interference case, days ahead of the scheduled Oct. 23 start of their trial.

Jan. 6 election interference

Trump lawyers to appeal gag order ruling

Key players: Judge Tanya Chutkan, Trump lawyers John Lauro, Todd Blanche

  • Attorneys for former President Donald Trump told a D.C. federal court Tuesday that they intend to appeal a limited gag order imposed by U.S. District Judge Tanya Chutkan.

  • The order handed down Monday by Chutkan prohibits Trump from attacking special counsel Jack Smith, possible witnesses or court staff.

  • Trump lawyers Lauro and Blanche filed a notice of appeal on Tuesday, signaling that they will appeal Chutkan’s ruling to the U.S. Court of Appeals for the D.C. Circuit.

  • According to Bloomberg, Trump’s team is expected to ask Chutkan to pause the gag order until the appeal process is complete.

  • Chutkan isn’t the only judge to issue a gag order in a case against or involving Trump. On Oct. 3, New York Judge Arthur Engoron, who’s presiding over the $250 million civil fraud trial, issued an order forbidding Trump from making online posts or other public statements about court staff after Trump made a derogatory post about Engoron’s clerk.

Why it matters: Trump’s tendency to lash out against critics has now led to two gag orders against him, prompting the question of whether the former president will tamp down his frequent attacks and fully comply with the orders or face further potential penalties for failing to do so. Additionally, it remains to be seen whether the appeal will impact the scheduled trial date of March 4 for the Jan. 6 case. Trump’s lawyers have repeatedly sought to delay the trial until after the 2024 presidential election.

Georgia election interference

Judge denies Powell, Chesebro motion to dismiss in Georgia election case

Key players: Fulton Superior Court Judge Scott McAfee, Trump co-defendants Sidney Powell and Kenneth Chesebro

  • Pro-Trump lawyers Sidney Powell and Kenneth Chesebro, who are among the 18 people facing charges with Trump in the 2020 election interference case in Georgia, lost their bids to get the criminal counts against them dismissed.

  • Judge Scott McAfee on Tuesday denied requests from Powell and Chesebro to dismiss the charges against them. McAfee concluded in his motion that the objections raised by the defendants failed to establish “a defect in the substance or form of the indictment.”

  • A group of potential jurors is expected to gather at the Fulton County courthouse on Friday to begin the jury selection process for Powell and Chesebro’s trial which is slated for Oct. 23. ABC News reports that McAfee will tell jurors to expect a five-month trial.

Why it matters: The latest ruling in Powell and Chesebro’s cases indicate that the two will likely stand trial on the scheduled date of Oct. 23, and would be the first defendants in the Georgia case to do so. Previous reports said that prosecutors considered offering plea agreements to Chesebro and Powell, but such deals would likely require future cooperation from the pair.


Tuesday, Oct. 17


Former President Donald Trump

Donald Trump at his civil fraud trial in New York City on Tuesday. (Andrew Kelly/Pool/Getty Images) (Pool via Getty Images)

On the same day the judge overseeing the federal case relating to the efforts to overturn the 2020 election issued a limited gag order prohibiting former President Donald Trump from attacking prosecutors, witnesses or court staff, Trump was back at a Manhattan courthouse for his $250 million civil fraud trial — and back to attacking the lead prosecutor in that case.

New York civil fraud trial

Trump lashes out at James

Key players: Letitia James, Michael Cohen

  • Speaking outside the courtroom upon his arrival, Trump tore into James, who brought the suit alleging that the former president and the Trump Organization deceived banks, insurers and others by massively overvaluing his assets and inflating his net worth on his financial statements. Trump said that James was “ranting and raving like a lunatic” and suggested she “shouldn’t be allowed to be attorney general” for bringing the case against him.

  • The former president seemed especially annoyed that James had cited in court the Palm Beach County tax assessor’s appraised value of Mar-a-Lago being between $18 million and $27 million as proof of fraud. Trump’s financial statements valued the property at between $400 million and $600 million.

  • Trump told reporters that Mar-a-Lago is “the most expensive house, probably, in the world,” estimating that the estate is worth between $1 billion to $1.5 billion and would “sell very easily.”

  • Inside the courtroom, Trump sat with his lawyers at the defense table listening to testimony from one of his company’s accountants, Donna Kidder about “the intricacies of internal spreadsheets,” the Associated Press said.

  • Trump, who attended the first three days of the trial, had planned his return to coincide with testimony from Michael Cohen, his former lawyer and fixer-turned star witness against him. But their anticipated face-off did not materialize, as Cohen’s testimony was delayed until at least next week due to an unspecified health issue. “I am thankful the medical condition, while incredibly painful, does not require an immediate procedure. I anticipate appearing as soon as the pain subsides,” Cohen said in a statement. “When I do testify, I am certain Donald will be in attendance, sitting with his lawyers at the defendant’s table.”

  • Trump told reporters that Cohen “didn’t have the guts” to appear.

Why it matters: Trump continues to lash out despite receiving two gag orders this month. On Oct. 3, New York Judge Arthur Engoron issued an order forbidding Trump from making online posts or other public statements about court staff after the former president made a derogatory post about Engoron’s clerk. And on Tuesday, Judge Tanya Chutkan, who is overseeing the federal Jan. 6 election interference case, formally issued a limited gag order prohibiting Trump from attacking special counsel Jack Smith, possible witnesses or court staff. Trump said he plans to appeal the ruling.

Former President Donald Trump

Trump speaking to reporters during a break in his trial. (Michael M. Santiago/Getty Images) (Michael M. Santiago via Getty Images)

“The judge said basically I don’t have the right to speak,” Trump told reporters outside his civil trial. “My speech has been taken away from me. I’m a candidate that’s running for office, and I’m not allowed to speak.”

FBI lawsuits

Trump to be deposed in suits against DOJ brought by Strzok and Page

Key players: Peter Strzok and Lisa Page

  • Trump was also expected on Tuesday to be deposed in a case involving Peter Strzok and Lisa Page, former FBI officials who he has long disparaged since it was revealed they were critical of Trump in private text messages to each other during then-special counsel Robert Mueller’s investigation into Russian meddling in the 2016 presidential election.

  • The former president is scheduled to testify in the two-hour, closed-door deposition in New York City in relation to their separate lawsuits against the Justice Department.

  • Strzok alleges that he was wrongly terminated by the FBI. Page alleges that the public disclosures of those text messages by the DOJ amounted to “an unwanted invasion of privacy” and damaged her reputation.

Why it matters: Unlike the civil trial, which Trump is not obligated to attend, the deposition does take the president’s time and attention away from the campaign trail — and the myriad criminal charges he is facing.


Monday, Oct. 16


The E. Barrett Prettyman United States Courthouse

The Prettyman federal courthouse in Washington, D.C. (Mandel Ngan/AFP via Getty Images) (MANDEL NGAN via Getty Images)

Former President Donald Trump’s legal team was present at the E. Barrett Prettyman federal courthouse in Washington, D.C., Monday morning for a hearing about whether Trump would be faced with a gag order in the federal case relating to the efforts to overturn the 2020 election. Trump has made disparaging remarks about numerous individuals, including prosecutors and witnesses. Meanwhile, a hearing on his lawsuit against a former British spy took place across the Atlantic.

Jan. 6 election interference

Consideration of the gag order

Key players: Judge Tanya Chutkan, Trump lawyer John Lauro

  • Chutkan said she would issue a “narrowly tailored” order that would not prevent Trump from broad criticisms of Washington, D.C., or the government. Trump will be able to attack President Biden and repeat his claim that the case is politically motivated.

  • However, he will not be able to make statements about special counsel Jack Smith or witnesses; the judge said his presidential candidacy does not give him the privilege of conducting a “smear campaign.”

  • Included among the targets of Trump’s invective have been the prosecutors (whom he called “a team of thugs”), his former Attorney General William Barr (a “gutless pig”) and former chairman of the Joint Chiefs of Staff Mark Milley (suggested he might deserve to be executed).

  • Trump attorney Lauro made the case Monday that threats or acts of violence by supporters of the former president weren’t enough to curtail his client’s free-speech rights, saying, “Are we going to tell Americans that they can’t speak because some crazed person might do something inappropriate? That would end the First Amendment as we know it.” Lauro also called it “an order of censorship.”

  • Lauro returned to an argument he has made often, suggesting the trial could be delayed until after the 2024 election. Chutkan has floated the possibility of moving up the start date of the trial — currently set to begin on March 4 — in order to avoid a tainted jury pool.

  • Trump chose to campaign in Iowa instead of attending the hearing.

Why it matters: If Trump violates the gag order, Chutkan said she would consider sanctions, which could range from warnings to jail. With Trump set to be making numerous campaign appearances in the coming months and his frequent postings to social media, a gag order violation seems possible if not likely.

Steele dossier civil suit

Trump seeks relief against former British spy

Key player: Intelligence consultant Christopher Steele

  • Trump is suing Steele and his firm Orbis Business Intelligence in British court under data protection laws.

  • The Steele dossier was assembled during the 2016 campaign and then leaked to BuzzFeed in early 2017, when it was subsequently published by the outlet. It contained numerous allegations, including many tying Trump to the Russian government.

  • “A judgment of the English court on this issue will be an immense relief to me as it will completely confirm the true position to the public at large,” read a witness statement prepared by Trump during a hearing Monday, adding, “Until there is such a judgment, I continue to suffer damage and distress as a result of people wrongfully believing that the data in the dossier is accurate.”

  • “It’s uncontroversial for me to say that President Trump is a controversial figure,” said Trump lawyer Hugh Tomlinson. “His interactions with the U.S. legal system have been many and varied, but we say none of this is relevant.”

  • A similar case by Trump against Steele was dismissed in the United States last year.

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