• Show Notes

The first criminal trial of a former U.S. president is really, truly, actually happening, and soon – 31 days from now, to be precise. Judge Juan Merchan has denied the defendant’s last-ditch request for a postponement, and now it’s on: March 25, downtown Manhattan, State of New York v. Donald John Trump

But the pivotal player at trial won’t be Trump himself. Allow me to gaze into my Crystal Ball of the Obvious and foretell that Trump will feign like he might take the stand but then play it safe and give it a pass. Instead, the center of attention at the trial will be the former president’s former fixer, Michael Cohen. 

First, a disclosure: Cohen and I are friends. I like him. I’ve been on air with him, and I’ve done his podcast several times. Our conversations sound like two aggressive cousins jawing at each other; I’ll tell him directly why he’s a flawed witness (though, as we’ll discuss shortly, not necessarily fatally flawed), and he’ll push right back. I invited him to both of my book launches. He couldn’t make the first one because he was finishing his federal sentence on house arrest – a perfectly sound excuse – but he came to the second. 

Turns out, I’m naturally drawn to rogues, and they trust me. As an organized crime prosecutor, I built cases on testimony from men who’ve done far worse things than Cohen ever even dreamt of. I’ve stayed in touch with some of them, and we’ve built relationships that now extend beyond our careers as prosecutors or gangsters. (If you’ve listened to Up Against the Mob, you’ve heard me catch up with some of them.) A colleague asked me recently: If I added up the number of murders committed by all the people in my phone contacts, how many would that be? I did some math and came up with 11 — not counting attempts and conspiracies, that’d be more.

So I’m no pearl-clutcher when it comes to putting a convicted felon on the witness stand. When Cohen testifies in the upcoming Trump trial, he’ll be the prosecution’s most important witness – and he’ll present an especially tricky case. (Another disclosure: Manhattan District Attorney Alvin Bragg is also a friend and a former colleague. I don’t know what to tell you, it’s a small world.) 

On paper, Cohen is an absurdly easy target for cross-examination. Ideally, prosecutors want a witness with no ax to grind; I once had a cooperator testify that he still loved the defendant and hoped he would beat our case – and that was good testimony for us. But Cohen has built his public profile largely on his visceral (and, at times, unhinged) hatred for his former boss. Cohen has publicly called Trump “batshit crazy,” the owner of a “mushroom pecker,” and – sorry, I’m just quoting him – “Donald Von ShitzinPantz.” In one machine-gun rant from his memoir, Cohen calls Trump “a cheat, a liar, a fraud, a bully, a racist, a predator, a con man.” Cohen is so at ease with his feelings that, in a perverse sense, he actually bolsters his own credibility. At least he’s deadly honest about where he stands.

Honesty has not, of course, been a traditional Cohen hallmark. We’re all familiar with his past life, when he was a growling, bare-knuckled taxi cab-medallion lawyer-turned-Trump-enforcer. The end result: Cohen pled guilty and served time at the Otisville Federal Correctional Institute for crimes including lying to Congress, tax fraud, bank fraud, and campaign finance fraud (the last one for the same hush money payments at issue in the upcoming trial). Meanwhile, Trump skated – until his 2023 indictments, at least, with the final result still undetermined. 

Because of Cohen’s history, prosecutors unavoidably must ask the jury to believe a star witness who has a long track record of lying. The defense attack will be simple and compelling: He’s a proven liar who took that same oath before and broke it – how can you believe him now? 

It’ll be the Manhattan DA’s job to convince the jury that Cohen has come clean. We can all understand the basic character arc here: Trump’s lying lawyer saw the light, admitted his conduct, paid the price, and now has gone straight. But it’s not quite that simple. (It never is, with Cohen.) He pled guilty to tax fraud for conduct relating solely to his own finances, so the DA can’t argue that he only committed crimes for Trump. Worse, Cohen now claims that when he took that guilty plea in 2018, he actually was not guilty, and he lied (again, under oath) when he told a federal judge that he had committed tax fraud. And Cohen recently got mixed up in a bizarre incident in which he gave fake, AI-generated legal citations to his personal lawyer, who then submitted them to a court. Cohen has said this was an accident, and I believe him, but the incident could provide more ammo for cross-examination.

Prosecutors and Cohen got some (mostly) good news last week. The state judge presiding over the New York AG’s civil fraud lawsuit against Trump credited Cohen’s testimony in that trial, which yielded a galactic verdict of over $350 million against Trump and his businesses. Judge Arthur Engoron found that Cohen’s testimony was “significantly compromised” by his extensive rap sheet and by “seeming contradictions in what he said at trial.” (That last part would particularly concern me, as a prosecutor.) But the judge concluded that, overall, Cohen’s testimony was credible, given his mannerism in the witness box and the independent, corroborating evidence. 

Corroboration is the key here. Prosecutors are obsessed with finding evidence that might support a dicey witness like Cohen. I once did a case where the cooperator mentioned offhand that he’d occasionally go to the supermarket with the defendant. Those trips had nothing to do with the charged crimes, but we subpoenaed the supermarket’s surveillance video anyway. (I’ll put you out of your suspense: we did find footage of the two men bagging up their groceries together, but we didn’t use it at trial because, well, it was pointless.) That’s how far prosecutors will go to find evidence that supports a cooperating witness. 

Cohen has claimed publicly that his testimony at the upcoming Trump trial will be heavily corroborated by independent evidence. Indeed, we know there are a series of checks, some signed by Trump, that were paid to Cohen to reimburse him for making hush money payments to the silence-ee, the adult film actress Stormy Daniels. That’s important evidence for prosecutors, of course, but it doesn’t quite provide the vital external support Cohen’s testimony requires. 

It’s important here to understand the precise charges facing Trump. He’s not charged with paying hush money; that’s seedy but not illegal. The crime here is falsifying the business records – specifically, prosecutors allege, Trump mislabeled those payments as “legal fees.” The payments aren’t the crime; it’s the booking of those payments. And on that point, there’s no known document that directly ties Trump himself to the internal accounting; Trump will argue that he left that part up to his attorney (Cohen) and accountants, as top executives often do. It’ll largely come down to Cohen’s word, standing alone, to rebut that defense. 

When Cohen takes the stand, it’ll be a moment of truth for him and for his former client. Prosecutors must convince the jury to credit Cohen, and the verdict likely will follow accordingly. Personally, I believe Michael, for the most part. I don’t think he fabricates, not anymore. He does tend to add a little oomph here and there, and his emotions can drive and color his perception. Cohen makes me roll my eyes sometimes, but I trust him, at bottom. The question now is whether twelve randomly-chosen Manhattanites will feel the same.