• Show Notes

Dear Reader,

There’s a time and a place for everything. For criminal charges relating to Donald Trump’s payment of hush money to Stormy Daniels, the time was two years ago and the place was the U.S. Department of Justice.

Instead, the Manhattan District Attorney seemingly is about to file charges against Trump that would be, at once, both monumental and piddling. We might be on the brink of history, but we are also looking at a case that, whatever the outcome, will amount to a prosecutorial and political anticlimax. 

If the DA, Alvin Bragg, chooses to indict Trump, he will become the first prosecutor in United States history to bring criminal charges against a former president. (My standard disclosure here: Bragg is a personal friend and a former SDNY colleague.) That’s a big deal, from any perspective. But we need to be realistic about the chance that this prosecution ultimately succeeds and, even if that comes to pass, the practical impact of a conviction. If you’re hoping to see Trump wearing an orange jumpsuit at Rikers Island, prepare for disappointment.

First, let’s get ourselves oriented. These charges, if they materialize, will come from the Manhattan DA – an elected, county-level prosecutor who can charge New York state-level laws. This is not the feds, this is not the Justice Department, this is not the SDNY. 

And that brings us to our first issue: the conduct here makes for an awkward fit under New York state law. It seems the DA will charge Trump with violating a New York statute against falsification of business records; the idea is that Trump phonied up documents claiming that the hush money payments were legal fees paid to Michael Cohen, who was then Trump’s attorney and bag man. That part is fairly straightforward – but it’s also just a lowly misdemeanor, as we’ll discuss further in a moment. To ratchet it up to a felony, prosecutors also must prove that Trump falsified those documents to further or conceal some other crime, most likely a violation of campaign finance laws. But it’s unclear whether a violation of federal campaign finance laws (which would apply to the presidential election) can trigger these state-level criminal laws. So this is a bank-shot of sorts, a dicey two-step with an uncertain outcome. 

Even if New York prosecutors do convict Trump, he’s almost certainly not going to prison. If they only prove the business records crime, that’s a misdemeanor – on the same plane, legally, as shoplifting less than $1,000 worth of goods from, say, a Walgreens. Nobody’s getting locked up for that. And even if prosecutors prove the more serious variation by tying the business records to a campaign finance crime, that’s a Class E felony. That’s Class “E” as in A through E, with A the most serious and E the least (and there is no F). This one is legally akin to shoplifting more than $1,000 worth of goods from, for example, Saks Fifth Avenue. The max penalty is four years, but the odds are long that a judge would send a septuagenarian, first-time, nonviolent offender to lockup for the least serious felony on the books. 

Beyond legal consequences, Trump faces limited if any political fallout. (Some argue that a prosecution that is broadly perceived as an overreach could rally political support for Trump.) Anyone who thinks a Trump indictment here will “take him out” of the 2024 race – think again. Legally, there is nothing barring a person from running for or holding office while under indictment. Even a conviction – heck, even imprisonment – wouldn’t do the trick, as a purely legal matter.  

And conviction is far from certain here. Remember that the famously (or perhaps notoriously) aggressive SDNY considered charging Trump for the hush money payments back in January 2021, when he left office. They passed, for reasons factual (some felt the proof was just barely sufficient to indict), legal (there were tough questions about establishing Trump’s knowledge and intent), and political (the SDNY was wary of bringing the first-ever charges against a former president, given the largely administrative nature of this conduct). (I give all the behind-the-scenes details on these internal SDNY deliberations in my new book, if you’re curious.)  

Based on what is known publicly, the DA’s evidence, on the whole, is chargeable, though certainly not a slam dunk. The prosecution faces substantial problems, starting with the passage of time. The hush money payments were made six and a half years ago, back in 2016. That’s an eternity by prosecutorial standards. That matters because conduct that is temporally distant tends to feel less urgent, less important, to a jury — and to the public, who rightly might wonder why Bragg is dredging up this old conduct now, so long after the fact (and shortly after he took heat – wildly unfairly, in my view – for declining to charge Trump last year on a separate financial case). The DA should be fine on the statute of limitations, by the way. Typically, charges must be brought within five years of the end of a crime, but New York prosecutors can rely on a state law that extends that period while a defendant continuously resides out of state. 

It seems the Manhattan DA intends to bank heavily on Cohen’s testimony. (Another disclosure: I am friendly with Cohen, and have been a guest on his podcast several times.) While I personally believe Cohen’s claims that Trump knew and understood the campaign-related and illegal purpose of the hush money payments – the key intent issue – it’s far from certain that he’d hold up at trial. He is a convicted perjurer and fraudster. He previously said to the New York Times and the Federal Election Commission that the payments were not made for campaign-related purposes (and hence were not illegal). And he won’t exactly present as an even-keeled, impartial witness; the man has built his public profile on his white-hot, all-consuming personal hatred for Trump. (Quick story: during one podcast taping, Cohen’s language towards Trump became so foul that I had to pause the interview and tell him and his producers that they’d need to edit out what he had said, or else I was leaving. And readers of this column know that I’m no pearl-clutcher when it comes to profanity.) Finally, remember that the SDNY rejected Cohen as a cooperator based on his lack of credibility. Federal prosecutors wrote to a judge in 2018 that, while Cohen “did provide information to law enforcement,” his “description of those efforts is overstated in some respects and incomplete in others… While he answered questions about the charged conduct, he refused to discuss other uncharged criminal conduct, if any, in which he may have participated.”

Still, there is a case to be made here. Prosecutors have the checks that Trump’s corporate entities used to reimburse Cohen for the hush money payments. They have Trump’s original false denial that he knew anything at all about the scheme. Prosecutors can point to the conspicuous timing of the payments (made just weeks before the 2016 election, when the alleged affair had happened nearly a decade prior). They’ll have Cohen’s first-hand testimony about Trump’s knowledge and involvement in the scheme. And the DA may have gathered more evidence than is publicly known. Trump insiders Kellyanne Conway and Hope Hicks both testified recently in the grand jury, for example; if either directly pins culpability on Trump, that would bolster the prosecution’s case. 

The DA’s office will need all the help they can get. Keep in mind that a prosecutor has essentially no margin for error. You need all twelve jurors to find guilt beyond a reasonable doubt. Eighty percent is a landslide in the political world, but it’s a loss for prosecutors (technically a mistrial, capable of being retried, but a disastrous outcome). If a single juror likes Trump, or thinks prosecutors have piled on for political reasons, or has doubts about Cohen’s veracity – then there will be no conviction. Even in heavily-blue, liberal Manhattan, a guilty verdict is far from certain.

It’ll be a big moment if and when Trump is indicted. He will face potential criminal consequences for the first time, after years of ostentatiously flouting the law. But a conviction won’t be easy and, even if it happens, it won’t result in anything like the comeuppance that some have dreamed of. Yes, this is a genuine bombshell. But it’s also likely to land with a dud.

Stay Informed,


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