Trump and Hush-Money Trial’s Central Witness Share a Tortured History

When Michael Cohen took the stand in Donald Trump’s criminal trial on Monday, it marked a climax in the real-life tale of ambition and betrayal that has unfolded between the two men over nearly two decades.

In the New York City courtroom, Cohen will be just a few yards away from the man he once looked up to as a paragon of raw power and heady glamor. Trump will have to sit quietly and hear directly from his former company lawyer’s mouth how Cohen—weeks before the 2016 election—paid adult film actress Stormy Daniels to stay silent about an alleged tryst with Trump, and how those reimbursements were allegedly masked in company records as legal fees. Trump denies he had an encounter with Daniels and has pleaded not guilty to 34 counts of financial fraud related to how the payments were logged.

The saga between Michael Cohen and Donald Trump sheds light on how Trump has operated for decades, bringing people into his thrall and abruptly cutting them loose when they’ve lost their utility. Few former Trump allies have turned on him as publicly as Cohen, who served time in jail for crimes related to work he did for Trump, including those payments to Daniels. It’s that tortured history that makes Cohen such a challenging witness for prosecutors. He’s a central player in the case against Trump and yet he’s a convicted felon.

“I have been living in a personal and mental incarceration ever since the day that I accepted the offer to work for a real estate mogul whose business acumen that I deeply admired,” Cohen told a federal judge in 2018 as he was sentenced to three years in prison for campaign-finance violations and other crimes. “In fact I now know there is little to be admired.”

When Cohen first started working for Donald Trump in 2006, Cohen, by his own account, was a little-known Manhattan attorney taking the money he made from personal injury and medical malpractice cases and investing it into taxi medallions—and apartments in Trump-branded buildings. But when Trump brought him in to use strong arm tactics with a building board, Cohen found he relished the rush of working in Trump’s orbit. (Trump gave Cohen a copy of an impassioned speech he’d made while trying to stack a board in Trump’s favor—in a gilt frame, of course.) 

Within a few years, Cohen had his own office in Trump Tower and, according to Cohen’s memoir, Disloyal, Trump was at the bar mitzvah of Cohen’s son, telling both of them, “You’re family.”

By the time Trump was the Republican candidate for President in 2016, Cohen had become a point of contact for dozens of Trump’s acquaintances and business associates. Most relevant for Alvin Bragg, the Manhattan District Attorney, those associates included David Pecker, who was publisher of The National Inquirer at the time, and testified on April 26 that he helped suppress stories that could have damaged Trump’s 2016 presidential campaign.

In his memoir, Cohen described himself as a one-time “acolyte” of Trump, one who, to the frustration of his own wife and family, was completely taken by the intoxication of the real estate mogul’s presence and approval. 

Trump fed him a fantasy like “a confidence artist” and was “showing me that he inhabited a different type of reality, one that he would share with me alone, a world that was filled with wonder and excitement and power and intrigue and adulation,” Cohen wrote. “All I had to do was what I was told, without question or a second thought.”

But that gossamer bubble began to lose its sheen when Trump won the White House, cut Cohen out of a role in Washington, gave him an annual bonus that was a third of the year before, and, according to Cohen’s account, slow-walked reimbursing Cohen for his payout to Daniels. Those reimbursements caught the eye of Special Counsel Robert Mueller who was investigating links between the Trump presidential campaign and Russia, and when Cohen’s office was raided by FBI agents in April 2018, Cohen says Trump spoke to him on the phone and told him “Stay strong, I have your back. You’re going to be fine.” 

It was the last time Cohen talked to Trump, Cohen wrote in his memoir. Over the next several months, Cohen initially agreed to enter into a joint defense agreement with Trump and others in his orbit. He also admits he lied to Congress when he testified about conversations he had with Trump over a Russian real estate deal. “I lied and lied and lied,” he wrote in his memoir. When the Department of Justice charged him with crimes related to his taxi medallion business, tax filings and his payments to Daniels, he decided to plead guilty for a reduced sentence. That was the moment he turned on Trump. 

Cohen was sentenced to three years in prison for financial crimes and lying to congress. During the pandemic lockdowns, he was released from the Otisville Correctional Facility in New York after a year of confinement.  He was briefly sent back for allegedly violating the terms of his release by continuing to work on his memoir and moving forward with plans to publish it.

In recent years, Cohen’s been a prime target of Trump’s ire, with the former President calling his former fixer a “fraudster,” “a proven liar,” and “a disgraced felon." Trump has continued to launch attacks against Cohen as the criminal trial ramped up, part of the reason Judge Juan Merchan imposed a gag order on Trump saying he can’t publicly criticize jurors, lawyers and potential witnesses. 

Despite the animosity between them, Trump’s and Cohen’s lives remain intertwined in multiple ways. Cohen still lives in Trump Park Avenue, a Trump-branded building in Manhattan. And last year, Cohen was a player in Trump’s civil fraud trial, testifying that he had helped manipulate the value of Trump’s assets on financial statements used to help Trump secure loans and other deals. Trump reportedly stayed out of the courtroom as his former fixer delivered the damaging testimony. 

Trump doesn’t have that option in his criminal trial. Should Cohen testify, the two will be face to face once again, after all these years.