From Trump loyalists to state witnesses: The evolution of 3 ex-members of Trump’s legal team

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In November 2020, Donald Trump mobilized a team of lawyers to help challenge the presidential election results. Their aim was to push state legislators to unlawfully appoint presidential electors and make baseless claims that voting machines were tampered with.

Nearly three years later, these same lawyers are abandoning the former president with guilty pleas to Georgia prosecutors. Trump and 18 allies were indicted in August on racketeering charges stemming from their efforts to overturn Joe Biden’s victory in Georgia.

Over the past week, three Trump-affiliated lawyers — Jenna Ellis, Kenneth Chesebro and Sidney Powell — struck plea deals that will allow them to avoid prison. The three guilty pleas could spell bad news for Trump because the deals require all three lawyers to cooperate with prosecutors and potentially testify for the state at trial.

Here is how the former president’s lawyers went from having his back to turning against him.

Jenna Ellis

Before she became part of team Trump, Ellis was a staunch critic of the former president, calling him an “idiot” in 2016. But the attorney became a Trump campaign adviser in November 2019 and was soon known for going to bat for him on TV and social media.

“In 2016, people were hesitant because they weren’t sure that President Trump would fulfill his promises, as opposed to the 2020 election where he has a track record where he has been so pro-American family,” Ellis said in an appearance on Fox Business in August 2019.

After the election, Ellis became part of a legal team challenging the results. She often traveled with Rudy Giuliani to various Biden-won states and pushed Republican lawmakers to appoint alternate slates of presidential electors.

“I’m so proud of this president. That President Trump is completely behind protecting election integrity and is making sure that the people and these corrupt election officials, from governors to secretaries of state all the way down to these local election officials, that they don’t get away with this,” Ellis said after the election in November 2020.

Prosecutors charged Ellis in August with a felony for participating in an effort to make false statements to Georgia lawmakers about election fraud. She pleaded guilty Tuesday.

Ellis had distanced herself from the former president, calling him a “malignant narcissist” on her radio show in September. She tearfully expressed remorse to the judge in her plea.

“What I did not do but should have done, your honor, was to make sure that the facts the other lawyers alleged to be true were in fact true,” Ellis said in court Tuesday. “In the frenetic pace of attempting to raise challenges to the election in several states, including Georgia, I failed to do my due diligence.”

Kenneth Chesebro

Chesebro worked as an outside adviser to the Trump campaign and was a behind-the-scenes architect of the far-fetched legal arguments that Trump used to justify his last-ditch attempt to remain in power.

Chesebro sent memos in November and December 2020 to James Troupis, a former Wisconsin judge and a lawyer with the Trump campaign who asked for Chesebro’s help on campaign litigation in Wisconsin, describing the push to send pro-Trump electors to Congress as a way to preserve Trump’s chances to win in post-election legal battles. But when those courtroom battles all fizzled, Chesebro’s rationale for the false electors evolved, and he noted that pro-Trump members of Congress could invoke them to potentially flip the Electoral College to Trump on Jan. 6, 2021.

Chesebro has largely stayed quiet about his involvement in efforts to overturn the 2020 election. In an interview with Talking Points Memo in June 2022, he said that it was the “duty of any attorney to leave no stone unturned in examining the legal options that exist in a particular situation.”

“Lawyers have an ethical obligation to explore every possible argument that might benefit their clients. In my work for the Trump-Pence campaign, I fulfilled that ethical obligation,” Chesebro told the outlet.

Chesebro pleaded guilty last week to a single felony count of conspiring to file false documents.

Sidney Powell

Powell became prominent during the Trump presidency as the attorney for Michael Flynn, who served as Trump’s first national security adviser, later pleaded guilty to lying to the FBI and was eventually pardoned by Trump. Powell was later hired to Trump’s legal team to challenge the results of the 2020 election.

The firebrand attorney is best known for speaking to the media, particularly Fox News, about conspiracy theories of foreign governments manipulating voting machines. Despite being pushed away by the Trump campaign soon after the 2020 election, Powell continued to advise Trump.

“This is stunning, heartbreaking, infuriating and the most unpatriotic acts that I can even imagine for people in this country to have participated in any way shape or form. And I want the American public to know right now that we will not be intimidated,” Powell said at a press conference after the election that is best remembered for the image of Rudy Giuliani’s hair dye running down his face.

Powell appeared in the Oval Office in December 2020 to push Trump to use the military to seize voting machines. Trump came close to appointing her special counsel and empowering her to lead that effort before rejecting it amid pushback from White House advisers.

“Most of us there knew something very wrong had happened,” Powell said in an August 2021 interview. “It was obvious to me from the mathematical and statistical impossibilities that occurred the night of our election. I already had some knowledge of the ability of voting machines to be tampered with.”

In the Georgia indictment, prosecutors accused Powell of leading an effort to illegally breach voting equipment after the election in Coffee County, Ga.

Last week, Powell pleaded guilty to six misdemeanor counts to commit intentional interference with performance of election duties. Powell also agreed to testify against the other defendants in the case, including Trump.

Three days after Powell pleaded guilty, Trump claimed on his social media platform, Truth Social, that Powell was never his attorney.

“MS. POWELL WAS NOT MY ATTORNEY, AND NEVER WAS. In fact, she would have been conflicted,” Trump wrote on Truth Social.

In November 2020, however, Trump touted Powell as among “a truly great team, added to our other wonderful lawyers and representatives!”

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