A challenging star witness in Donald Trump’s hush money trial

He once said he would take a bullet for Donald Trump. Now Michael Cohen is prosecutors’ biggest piece of legal ammunition in the former president’s hush money trial.

But if Trump’s fixer-turned-foe is poised to offer jurors this week an insider’s view of the dealings at the heart of prosecutors’ case, he also is as challenging a star witness as they come.

There is his tortured history with Trump, for whom he served as personal attorney and problem-zapper until his practices came under federal investigation. That led to felony convictions and prison for Cohen but no charges against Trump, by then in the White House.

Cohen, who is expected to take the stand Monday, can address the jury as someone who has reckoned frankly with his own misdeeds and paid for them with his liberty. But jurors likely also will learn that the now-disbarred lawyer has not only pleaded guilty to lying to Congress and a bank, but recently asserted, under oath, that he wasn’t truthful even in admitting to some of those falsehoods.

And there is Cohen’s new persona — and podcast, books, and social media posts — as a relentless and sometimes crude Trump critic.

As Trump’s trial opened, prosecutors took pains to portray Cohen as just one piece of their evidence against Trump, telling jurors that corroboration would come via other witnesses, documents and the ex-president’s own recorded words. But Trump and his lawyers have assailed Cohen as an admitted liar and criminal who now makes a living off tearing down his former boss.

“What the defense is going to want the jury to focus on is the fact that he’s a liar” with a blemished past and a tetchy streak, said Richard Serafini, a Florida criminal defense lawyer and former federal and Manhattan prosecutor.

“What the prosecution is going to want to focus on is ‘everything he says is corroborated — you don’t have to like him,'” Serafini added. “And No. 2, this is the guy Trump chose.”

Cohen’s early-2000s introduction to Trump was a classic New York real estate story: Cohen was a condo board member in a Trump building and got involved on Trump’s side of a residents versus management dispute. The mogul soon brought Cohen into his company.

Cohen, who declined to comment for this story, had had an eclectic career that veered from practicing personal injury law to operating a taxi fleet with his father-in-law. He ultimately functioned as both a Trump lawyer and shark-toothed loyalist.

He worked on some deal-making efforts but also spent much of his time threatening lawsuits, berating reporters and otherwise maneuvering to neutralize potential reputational dings for his boss, according to congressional testimony that Cohen gave after breaking with Trump in 2018. The rupture came after FBI raided Cohen’s home and office and Trump began to distance himself from the attorney.

Cohen soon told a federal court that he had helped candidate Trump wield the National Enquirer tabloid as a sort of house organ that flattered him, tried to flatten his opponents and bottled up seamy allegations about his personal life by buying stories or flagging them to Cohen to purchase. Trump says all the stories were false.

Those arrangements, which Manhattan District Attorney Alvin Bragg’s office portrays as a multipronged scheme to keep information from voters, are now under a microscope at Trump’s hush money trial. He has pleaded not guilty to 34 counts of falsifying business records so as to veil reimbursements to Cohen for paying off porn performer Stormy Daniels. She claimed a 2006 sexual encounter with the married Trump, which the former president has denied.

Other witnesses have testified about the hush money dealings, but Cohen remains key to piecing together a case that centers on how Trump’s company compensated him for his role in the Daniels payoff.

Trump’s defense maintains that Cohen was paid for legal work, not a cover-up, and that there was nothing illegal about the agreements he facilitated with Daniels and others.

In criminal trials, many witnesses come to the stand with their own criminal records, relationships with defendants, prior contradictory statements or something else that could affect their credibility.

Cohen has a particular set of baggage.

In testimony, he will need to explain his prior disavowals of key aspects of the hush money arrangements and to convince jurors that this time he is telling the truth, the whole truth and nothing but the truth.

Still in the Trump fold when the Daniels deal came to light, he initially told The New York Times that he had not been reimbursed, later acknowledging repayment — as did Trump, who had previously said he did not even know about the Daniels payout.

Then, in the course of two federal guilty pleas, Cohen admitted to tax evasion, orchestrating illegal campaign contributions in the form of hush money payments, and lying to Congress about his work on a possible Trump real estate project in Moscow. He also pleaded guilty to signing off on a home equity loan application that understated his financial liabilities.

While many types of convictions may be used to question a witness’ credibility, when crimes involve dishonesty, “there’s a treasure trove of stuff there for a cross-examiner,” Serafini said.

Moreover, Cohen raised new questions about his credibility while testifying last fall in Trump’s civil fraud trial. During a testy cross-examination — he answered some questions with a lawyerly “objection” or “asked and answered” — Cohen insisted he was not quite guilty of tax evasion or the loan application falsehood. Ultimately, he testified that he had lied to the now-deceased federal judge who took his plea.

The fraud trial judge found Cohen’s testimony credible, noting that it was corroborated by other evidence. But a federal judge suggested that Cohen perjured himself either in his testimony or his guilty plea.

Since splitting with Trump, Cohen has confronted his past lies head-on. His podcast’s title – “Mea Culpa” – gestures at a reckoning with his crimes, and he acknowledged in the foreword to his 2020 memoir that some people see him as “the least reliable narrator on the planet.”

At his 2018 sentencing, he said his “blind loyalty” to Trump made him feel it was my duty to cover up his dirty deeds, rather than to listen to my own inner voice and my moral compass.” Outside court, he has cast himself as an avatar of anti-Trump sentiment. In social media salvos as the trial opened, Cohen used a scatological nickname for Trump, taunted him to “keep whining, crying and violating the gag order, you petulant defendant!” and commented acerbically on his defense.

The posts could give Trump’s lawyers fodder to paint Cohen as an agenda-driven witness out for revenge. In a nod to that vulnerability, Cohen posted two days after opening statements that he would cease commenting on Trump until after testifying, “out of respect” for the judge and prosecutors.

Yet in a live TikTok this past week, Cohen wore a shirt featuring a figure resembling Trump with his hands cuffed, behind bars. After Trump’s lawyers complained, Judge Juan M. Merchan exhorted prosecutors Friday to tell Cohen that the court was asking him not to make any more statements about the case or Trump.

To Jeremy Saland, a New York criminal defense lawyer and former Manhattan prosecutor, Cohen’s background is not such a hurdle for prosecutors.

“Where Cohen has the problem is: He doesn’t shut his trap,” Saland said. “He just constantly takes shots at his own credibility.”

Prosecutors will need to persuade Cohen to be forthright, acknowledge his past wrongdoing and rein in his freewheeling commentary, Saland said, or the case can become “the Michael Cohen show.”

Indeed, Trump lawyer Todd Blanche used his opening statement to hammer on Cohen’s “obsession” with Trump and his admitted past lying under oath.

“You cannot make a serious decision about President Trump relying on the words of Michael Cohen,” Blanche told jurors.

But prosecutor Matthew Colangelo characterized Cohen as someone who made “mistakes,” telling jurors they could believe him nonetheless.

Meanwhile, prosecutors have pointed to remarks Trump has made about Cohen and others to accuse him of multiple violations of a gag order that bars him from commenting on witnesses, jurors and some other people connected to the case. The judge has held Trump in contempt, fined him a total of $10,000 and warned that jail could follow if he breached the order again.

Prosecutors also have not shied from testimony about Cohen’s combative personality. A banker testified that Cohen was seen as a “challenging” client who insisted everything was urgent. Daniels’ former lawyer, Keith Davidson, described his first phone call with Cohen as a screaming “barrage of insults and insinuations and allegations.”

While such episodes might not be flattering to Cohen, eliciting them could be a way for prosecutors subtly to indicate he is not their teammate, but simply a person with information, said John Fishwick Jr., a former U.S. attorney for the Western District of Virginia.

“It’s a way to try to build up his credibility while you distance yourself from him,” he suggested.

When Cohen takes the stand, prosecutors would be wise to address his problematic past before defense lawyers do, said New York Law School professor Anna Cominsky. She taught a course with Bragg before he became district attorney, but she offered comments as a legal observer, not someone privy to his office’s strategy.

“I imagine in their closing arguments,” Cominsky said, “that the prosecutor is going to look right at the jury and say, ‘This is not a perfect witness, but none of us are.'”