Has CFO Allen Weisselberg Finally Flipped on Trump?

Photo by John Minchillo, AP

Allen Weisselberg has hired new lawyers.

For many laypeople, that might not sound like big news. But to legal observers, it’s a possible bombshell.

Throughout his and the Trump Organization’s criminal trial for tax fraud, at least two things held true: Weisselberg repeatedly refused to turn on his former boss, and his former boss, via the Trump Organization, was paying his lawyers’ fees. Now NBC reports that Weisselberg has hired his own lawyers, meaning he is no longer represented by the ones that came with serious strings.

That means one of a few things, but if it means what many suspect is likely—that Weisselberg has finally flipped on Trump—that is a huge story and could explain a lot of what has been going on behind the scenes. 

Let’s walk through some scenarios and then game out the third and most likely one.

The possible reasons behind Weisselberg changing lawyers 

Possibility #1: He wasn’t feeling it. Before we get too excited, there may be a very banal reason for Weisselberg to change his legal team. It’s possible, for example, that Weisselberg just didn’t like his lawyers or the deal they got him. One of the lawyers, Nicholas Gravante, was relatively new to Weisselberg. He managed to get Weisselberg a sweetheart deal in terms of a prison sentence: just five months out of a possible 12 years, in exchange for cooperation against the Trump Organization but notably not against Donald Trump himself. Firing him now for doing a “bad job” doesn’t make much sense—unless something has come up that Gravante didn’t anticipate, such as the risk of further criminal charges (more on that below).

But as Anna Bowler of the Lawfare blog notes, the other lawyer he fired, Mary Mulligan, is Weisselberg’s longtime lawyer. She was representing him as recently as January, when he began serving his sentence at Rikers. Breaking up with her is a very big deal. Years of communication and rapport with a trusted legal advisor is not something you walk away from lightly. It makes little sense that Weisselberg would change teams simply because he was unhappy with them.

Possibility #2: Trumpworld just wasn’t happy with Weisselberg. The Daily Beast has a different take on the development. Its sources relayed that the Trump Organization was unhappy with how cozy Weisselberg appeared to have become in the waning days of the trial, right before the company was found guilty of 17 counts including tax fraud. It blamed newcomer to the legal team, Gravante, for not being “Trumpy” enough, and apparently Eric Trump made the call to replace him. But there was no mention in the reporting of Mulligan, who was also replaced, so something about this take doesn’t fill in all the gaps.

Further, a lawyer for the Trump Organization unequivocally disputed this version of events, saying that Weisselberg’s decision to change lawyers was “entirely his own.” Per reporting, Weisselberg is now being represented by Seth L. Rosenberg, who once ran the Rackets Bureau at the Manhattan DA’s office. 

Possibility #3: Weisselberg has flipped. Hoo boy. This would be a “yuge” problem for Trump. Did it finally happen?

In other instances, when a key witness who used to be represented by Trump-related entities such as the Trump Organization or the Trump Campaign abruptly changed to counsel not funded by those organizations, it has signaled that the witnesses decided to flip on Trump and his allies. This occurred with both Michael Cohen, Trump’s one-time “fixer” at the center of the Stormy Daniels hush money cover-up allegations, and with Cassidy Hutchinson, the one-time top aide to former White House chief of staff, Mark Meadows.

Changing counsel in the middle of serving a short prison sentence also makes little sense, unless (as I walk through below) something important has happened. So the question is, what might have caused Weisselberg to want to retain his own lawyers, at considerable personal cost, with no Trumpy strings attached?

Has Bragg put the squeeze on Weisselberg?

When Weisselberg was first sentenced, many observers, including me, were taken aback by the brevity of the sentence of just five months. Sure, it was in a dangerous and notorious prison, but with good behavior, Weisselberg could be out in just over three of those months. He’s currently on day 79. Why, we wondered, would Bragg let him go with just a slap on the wrist?

One possibility, posited at the time by Andrew Weissman writing in Just Security, was that Bragg intended to hold back other possible charges, first giving Weisselberg a taste of what it’s like to be in Rikers, even for a short time. Wrote Weissman,

[P]lea agreements typically include language that provides such protection, such as the defendant will not be prosecuted for “any crimes disclosed to the office” or “any crimes committed during the defendant’s time working at the company.” But the agreement with Weisselberg provides no protection whatsoever—not one word. Given Weisselberg’s experienced array of defense counsel, that is no oversight.

I concurred then, and I see the implications now. So what other charge could Bragg have held back? There is an obvious one: insurance fraud.

Enter Letitia James, the New York Attorney General currently suing the Trump Organization for false financial statements on inflated property values. In one of her filings, she laid out a possible open-and-shut insurance fraud case against Weisselberg. He had claimed, falsely, that the value of the Trump Organization’s real estate holdings had been assessed by an independent appraiser, but that turned out to be a lie. The insurer, Zurich North America, apparently relied on those assurances to renew the Trump Organization’s coverage.

If it’s easily provable that Weisselberg made those false representations, and that there never was an independent appraiser for the properties, that’s another crime. Moreover, it is one committed by someone who has already pled guilty to tax fraud. That means any new sentence could be far higher than a few months. A few years could effectively be a life sentence, especially at Weisselberg’s age. 

What would it mean if he really has flipped?

On the specific case about hush money payment cover-ups and a possible false business records charge, Weisselberg would be as critical a witness, if not more so, than Michael Cohen. This is because, at least according to Cohen, Weisselberg had direct knowledge of the deal with Stormy Daniels and was involved in discussions with Trump about whether she should be paid.  

Weisselberg was also involved in reimbursing Cohen for the $130,000 payment and helping to plan the deception. In his book Disloyal, Cohen relates how he and Weisselberg plotted the payoff in Trump Tower just weeks before the 2016 election. Cohen says it was Weisselberg who initially suggested faking business records. One idea was to run an invoice through the Trump National Golf Club or perhaps sell a Mar-a-Lago membership. “We definitely don’t want any paper trail leading back to the Boss… if the Boss pays it and signs the check, it’s like disclosing it to the world…. [I]t needs to come from a third-party to ensure secrecy,” Cohen quotes Weisselberg as saying.

Weisselberg corroborating Cohen would add considerable legal jeopardy for Donald Trump on the case, but it could also open a host of further charges against Trump, depending on how cooperative Weisselberg might become if he has indeed flipped. Trump has not yet been charged in any of an array of possible other crimes—such as tax fraud, money laundering, racketeering and falsifying documents—and that might be intentional. Maybe Bragg was waiting all along for Weisselberg to realize, after sitting in Rikers for nearly three months, that Trump isn’t worth a life behind bars.

But is there any evidence he has flipped?

Here we need to be cautious. Grand jury proceedings are secret, and as a convict, should Weisselberg testify before the grand jury, he would be brought in the back or side door. The media and the public would not know about it, for good reason.

There has been a great deal of speculation about why the grand jury continues to meet, and even still hear from witnesses, without an indictment being issued yet. Trump was invited recently to appear before it, which normally signals that the end of the grand jury’s work is near. On the other hand, the jurors are scheduled to go on a long-planned hiatus in April, so if they do not vote today or early next week to issue an indictment, we could be looking at late April at the earliest.

Of course, Trump will seek to capitalize upon any further silence or inaction by the grand jury. He would use it to suggest they had changed their minds because the case is falling apart at the last minute. I find a grand jury deadlock or hesitation fairly unlikely, but of course, I should add, it is theoretically possible.

But it is more likely, and quite possible given the news of a new legal team, that Weisselberg has finally flipped on Trump. If so, this could be what is causing all this shuffling and confusing signaling. A pending appearance by Weisselberg, for example, would surely be enough reason for the DA’s office to postpone final presentation and take additional time to prepare for that testimony, assuming of course that he hasn’t already come in. 

Patience, along with a deep and satisfying breath, is in order.

If in the end the story plays out like this, and Trump really does goes down like Al Capone for financial fraud because his CFO finally gives up the goods, all under very clever, incremental pressure from prosecutors, then we will owe the Manhattan DA a collective apology and some major props for playing the long game. He will have truly earned, shall we say, big bragg-ing rights.