Former Trump Lawyers Who Brutally Turned Their Back On Him

You have to hand it to Donald Trump's most loyal lawyer — Rudy Giuliani's legal woes might have changed his lavish life, but despite having to give up many of his prized possessions (including his license to practice law in Washington, D.C.), he hasn't turned on Trump. As a thank-you, the president has announced he will be presenting Giuliani with the Presidential Medal of Freedom. Given the infamous attorney's spotty record, Trump has effectively rendered the prestige of said medal null and void. 

There's a reason no other former Trump attorneys are in the running for the medal — they all swiftly turned on the divisive politician after finding themselves in hot legal water for trying to aid Trump in evading the law in one way or another. Michael Cohen, along with several others, is one of them. He is, perhaps, the most well-known Trump supporter-turned-critic that has emerged since the president's disgraceful exit from the White House in 2020 and was instrumental in Trump's subsequent hush money trial.

Trump has had no shortage of lawyers since some of his former attorneys brutally turned their backs on him. Alina Habba, who has been called out for being Trump's worst lawyer, certainly comes to mind. But Trump's new legal team would do well to remember what happened to his previous attorneys, and how the president had no problem throwing them under the bus to save his own skin. In retrospect, one can hardly blame Trump's former lawyers for trying to save themselves by turning on him. 

Michael Cohen used to be a Trump loyalist, until he realized his list of crimes would continue to grow the longer he stayed in the president's employ. He pleaded guilty to tax fraud and campaign finance violations in 2018 and was sentenced to three years in prison. He got a lucky break when the pandemic hit and served the rest of his time under house arrest.

During Trump's hush money trial, Cohen was a key witness and testified that he'd lied for Trump on many occasions and engaged in illegal activities on behalf of his client, which included making the hush money payment to adult film star Stormy Daniels. Cohen has also since admitted that he helped keep a lid on allegations from women who claimed Trump sexually assaulted them by buying their stories and ensuring they never made it to print. Cohen asserted that Trump's attorneys' main priority was to "do everything within our power to protect Mr. Trump," per the BBC. While testifying in front of Congress, he said, "Lying for Mr. Trump was normalized, and no one around him questioned it" (via The Atlantic).

When Cohen pleaded guilty, word on the street was that Trump was nervous about the consequences. "He is terrified. This is 40 years of deceit coming home to torment him," Trump biographer Michael D'Antonio told Politico at the time. Trump has since made sure to vilify his former attorney and fixer whenever he speaks of him. During a gaggle with the press in November 2018, Trump had nothing good to say about Cohen. "He's a weak person ... unlike other people that you watch," Trump said (via PBS NewsHour), adding that anything Cohen says against him is a feeble attempt to reduce his prison sentence.

Jenna Ellis, like Michael Cohen, will forever have a Trump-stained record. Serving as Trump's senior legal adviser from 2019 onward, Ellis was instrumental in aiding the president's narrative that the 2020 election had been rigged against him. She told Fox News in November 2020 that Donald Trump "won in a landslide" and also claimed that the president's legal team had proof that there had been a "coordinated effort in all of these states to transfer votes either from Trump to Biden, to manipulate the ballots, to count them in secret" (via Politico). Additionally, she insisted that some 500,000 illegal votes had been counted in Arizona, all of which were supposedly cast for Joe Biden.

After her misrepresentation of the facts landed her in hot water with authorities, Ellis admitted that the claims she had made about a stolen election were false. She opted to cooperate with authorities and help lead the investigation into Trump instead, after pleading guilty to a felony charge of trying to overturn the election results in Georgia. This was a bad look for Trump, with pundits predicting that his former team of lawyers could potentially cause the politician to end up behind bars (instead, he somehow ended up back in the White House).

While delivering a teary court testimony in October 2024, Ellis told the judge that she failed to fact-check the information she received from other Trump attorneys about the supposed election fraud before relaying it to the media and the public. "I believe in and value election integrity. If I knew then what I know now, I would have declined to represent Donald Trump in these post-election challenges." Ellis stated, adding, "I look back on this whole experience with deep remorse" (via PBS NewsHour).

When Robert Mueller investigated the possibility of Russian interference in the 2016 election, Ty Cobb was the one who represented the Trump administration. The fact that he never worked as Donald Trump's personal attorney is likely the reason he still has a license to practice law. Cobb became an outspoken critic of the president in his second term and gave White House Press Secretary Karoline Leavitt a scathing new nickname while he was at it.

After Trump indicted former FBI Director James Comey in September 2025, Cobb told CBS that the president's conduct was "wholly unconstitutional [and] authoritarian," adding, "Trump wants to rewrite history so that the next generation may not know that he incited a violent insurrection, refused to peacefully transfer the power of the presidency after losing an election, stole classified documents and showed them to friends and guests at Mar-a-Lago, and that he was a criminal."

Cobb doubled down on these claims during an interview with MSNBC, telling the outlet that Trump prosecuting his political enemies is a red flag that shouldn't be ignored, no matter what side of the party line you're on. He called the president a narcissist and accused him of "acting like a 2-year-old" and warned that anyone who finds themselves on the receiving end of the president's wrath has reason for concern.

Once upon a time, Sidney Powell was determined to help Donald Trump overturn the 2020 election. Trump notably called her a "GREAT LAWYER" in a 2019 X post, and gave her a shout-out in another post on the platform shortly after he lost the 2020 election. He touted Powell and the other attorneys aiding him as "a truly great team" who were going to help him "defend OUR RIGHT to FREE and FAIR ELECTIONS!"

By 2023, the jig was up. Powell, who vowed to "release the Kraken" in a Fox Business interview during which she peddled Trump's claims that the election had been rigged, cowered in the face of the lawsuits brought against her for attempting to overturn election results in Georgia (via The Hill). She pleaded guilty to the charges, and Trump swiftly distanced himself from her, taking to Truth Social to pen, "Despite the Fake News reports to the contrary, and without even reaching out to ask the Trump Campaign, MS. POWELL WAS NOT MY ATTORNEY, AND NEVER WAS" (via NBC News).

Legal experts noted that Powell, having been in Trump's inner circle (despite the president's hefty denials), could provide unique insight into what conspired in the days before the January 6 insurrection. Prosecutors offered Powell a deal in exchange for her cooperation in future lawsuits against Trump. In return for giving testimony about the president's activities before the insurrection, Powell received six years of probation instead of facing any jail time.

Former Trump lawyer Kenneth Chesebro turned against his former boss around the same time that Sidney Powell did. His rap sheet was equally long, with overwhelming evidence that he tried everything in his power to prevent the 2020 election results from being certified. In 2023, he pleaded guilty to conspiracy to commit filing false documents and opted for a similar plea deal as Powell — five years of probation, a hefty fee, and his testimony in future trials relating to the 2020 election and Donald Trump.

In the apology letter he was required to write to the citizens of Georgia, Powell didn't admit to any wrongdoing or that the 2020 election had not, in fact, been stolen from Trump. Of course, he was no longer of any use to the president, and in 2024, Chesebro's legal license was suspended after he entered another guilty plea regarding the overturning of election results in Georgia.