Donald Trump's Showdown With Michael Cohen Might Be His Downfall

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Trump is risking jail time if he breaks his gag order when Michael Cohen takes the stand in the New York fraud trial today, legal analysts have said.

Trump will now be challenged by the evidence of Michael Cohen, his former longtime attorney.

Cohen is expected to give evidence on Tuesday in New York Attorney General Letitia James' $250 million lawsuit. Trump is accused of inflating his net worth by billions of dollars to obtain benefits such as better bank loans and reduced tax bills between 2011 and 2021. Trump maintains his innocence in the case, accusing prosecutors of targeting him for political purposes.

Legal analyst Lisa Rubin said on X, formerly Twitter, on Tuesday that Trump "is already under a very narrow gag order" and that the judge "warned that future violations could result in much harsher penalties, including possible jail time."

"After that experience, how is Judge Engoron going to react if Trump goes after Cohen as he is testifying?" Rubin asked.

She also wrote that last week, during the testimony of appraiser Doug Larson, Trump's reactions "were distracting, loud and in the Attorney General's team's view, inappropriate. Judge Engoron asked everyone to keep their voices down, 'particularly if it's meant to influence the testimony.'"

Legal commentator and former Watergate prosecutor Jill Wine-Banks wrote on X on Monday that Cohen would be "a believable and unintimidated witness telling a narrative corroborated by documents."

"Tomorrow will be exciting. Will Trump control his rage?" she asked.

Newsweek reached out to Trump's attorneys via email for comment.

Cohen, a one-time Trump ally who turned on him after serving a sentence for making hush payments to adult film actor Stormy Daniels ahead of the 2016 presidential election, posted a message to Trump ahead of his testimony on X.

He warned Trump on Monday that he will continue to speak out against him, even if doing so is "exhausting."

"I will continue to speak truth to power...no matter Donald's continued smear and harassment campaign against me," he wrote, later adding that standing up to Trump is "exhausting to do so and Donald knows it."

"It's all about accountability! No one is above the law. #TeamCohen," he wrote in a separate post.

Cohen was initially scheduled to provide his testimony in the case last week, but it was delayed due to a health concern.

Donald Trump rally
Donald Trump speaks during a campaign rally in Derry, New Hampshire, on October 23, 2023. Michael Cohen, Trump's former attorney, is expected to give evidence against him a a civil fraud trial in New York... JOSEPH PREZIOSO/Getty Images

In a ruling last Friday, New York Judge Arthur Engoron fined Trump $5,000 for breaking the gag order and said the court "is way beyond the 'warning' stage."

"Make no mistake," Engoron added. "Future violations, whether intentional or unintentional, will subject the violator to far more severe sanctions, which may include, but are not limited to, steeper financial penalties, holding Donald Trump in contempt of court, and possibly imprisoning him."

Trump's niece, Mary Trump, an ardent opponent of his uncle, said last week on her video blog that she hoped that he would violate the gag order if it meant he would end up in jail and asked if there was anything she and her supporters could do to make it happen. Her guest, former attorney Joe Gallina, said Trump is in "serious legal jeopardy" and could face fines and imprisonment if he violates the gag order.

Engoron ruled last month that Trump, his adult sons and their businesses committed fraud and will now decide on six other accusations, including falsifying business records, insurance fraud, and conspiracy claims during the trial. Trump's attorneys did not request a jury, so Engoron will rule on the other accusations.

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About the writer

Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. He has covered human rights and extremism extensively. Sean joined Newsweek in 2023 and previously worked for The Guardian, The New York Times, BBC, Vice and others from the Middle East. He specialized in human rights issues in the Arabian Gulf and conducted a three-month investigation into labor rights abuses for The New York Times. He was previously based in New York for 10 years. He is a graduate of Dublin City University and is a qualified New York attorney and Irish solicitor. You can get in touch with Sean by emailing s.odriscoll@newsweek.com. Languages: English and French.


Sean O'Driscoll is a Newsweek Senior Crime and Courts Reporter based in Ireland. His focus is reporting on U.S. law. ... Read more