Alvin Bragg is widely viewed as struggling in his job as Manhattan DA. But is that assessment fair — should it be reevaluated with the benefit of hindsight and the developments over the past week in his office’s Trump investigation?

The initial assessment of Bragg as not ready for primetime was based on his issuance of a Day One memorandum limiting the circumstances under which his office would prosecute arrested suspects. That memorandum on its face had deep flaws that reflected a lack of robust internal vetting, and its public reception including by the NYPD, the Mayor’s Office, and the new Governor, revealed a lack of external vetting as well. The memorandum was quickly withdrawn, but the damage was done: his office’s ineptitude set back future initiatives of progressive prosecutors and created the lens through which all of Bragg’s subsequent acts would be judged.

We did not have to wait long. Close on the heels of the Day One memo fiasco, a second event solidified Bragg’s reputation. Bragg was subject to the public spectacle of two prominent lead prosecutors on his financial investigation of Donald Trump resigning from their positions, in what appeared to be caused by an internal dispute on the merits of a potential criminal indictment of the former president. To many in the public and media, it seemed inconceivable that Trump had not committed at least one prosecutable financial crime and that Bragg could responsibly come to a contrary conclusion so quickly in his tenure as DA.

That one-two punch was followed by a seeming knock-out blow when a resignation letter to Bragg from one of the lead prosecutors was leaked to the press, which stated categorically that in that person’s view there was a prosecutable case against the former president and, to twist the knife further, that Bragg’s predecessor had approved it going forward. The media reaction was furious and one-sided. The press neglected to note that the letter was not signed by the other lead prosecutor who resigned, barely covered that other career prosecutors disagreed with the letter’s assessment of the case, and failed to take the leaker of the letter to task as acting in a manner akin to James Comey — who was appropriately excoriated for his actions in July and October of 2016 when he publicly denigrated Hillary Clinton, a person not charged with a crime, based on evidence that was not public. 

Bragg was in no position to defend himself: like Attorney General Garland, he was rightly constrained about what he could say about someone who had not been charged. And Bragg’s claim that he could not speak about the ongoing investigation was met with derision. Few truly believed there was still an active criminal investigation after the departure of the two prosecutors (even though the remaining team was led by a highly regarded, experienced, prosecutor).

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Now is an appropriate time to ask whether the assessment of Bragg — which understandably was colored by his Day One memo and the lopsided press on the lead prosecutor resignations — was reached prematurely.

This past week the only person charged to date in the DA’s Trump investigation pleaded guilty in advance of an October 24, 2022 trial date — a trial in which the two remaining defendants are Trump companies controlled by the former president. 

Allen Weisselberg, the longtime CFO of the Trump Organization, pleaded to all 15 charges against him. He admitted to participating in a lengthy conspiracy in which he and other Trump company executives received millions of dollars of employment compensation hidden as untaxed perks, such as rent and utility payments for a swanky Manhattan apartment, luxury cars, and private school tuition. Both the executives and the companies benefitted financially from the scheme as they did not pay the requisite state or federal taxes on this compensation. 

The plea agreement does not follow the form routinely used for the DA’s plea or cooperation agreements. In fact, there isn’t even a written plea agreement; the terms were just orally articulated to the court at the plea hearing. The terms are equally bespoke, befitting the unique circumstances of this case, with plusses and minuses for both sides. 

Weisselberg got advantages out of the deal: He capped his sentencing exposure to 5 months in jail and was not required to fully cooperate, which would have meant disclosing all crimes he knows about, including his own and that of the former president. And although a 5-month sentence is within the heartland of sentences for a first-time tax offender — for someone who pleads guilty before trial and is 75-years old — the plea helped avoid the distinct risk that the court would have deviated from that norm in this high-profile case.

Bragg got a lot as well from the deal — and potentially a lot more than is visible now. At the most basic level, Bragg avoided the risk of trial and got a conviction on every single count of the indictment, with Weisselberg agreeing under oath to the veracity of all the allegations in the indictment against him and the Trump entities. And while a 5-month prison term even in Rikers Island is entirely unfair when compared to sentences handed out to non-economic crimes and non-white collar criminals, that inequity is pervasive in the courts, both state and federal, in sentencing rich, white executives (I personally saw it at play repeatedly in the Enron prosecutions). Here the state judge was reported to have signaled that he was going to follow this standard practice. But Bragg guaranteed that the 5-month term would be available to Weisselberg only if he was truthful in the upcoming trial and repaid all the money he owed as a result of the scheme. To make sure Weisselberg fulfilled these obligations before he got the benefit of the 5-month deal, Bragg made sure that sentencing be after the trial.

Bragg also greatly augmented the proof against the Trump entities in the upcoming trial. 

Under the state’s accessorial liability law, Weisselberg’s actions and intent as a “high managerial” employee are imputed to the Trump entities, unless the companies in essence can prove that Weisselberg lied in his plea and is not guilty – a steep hill to climb given the extensive proof in the case. But the defense runs a risk going down that path: it might win the battle but lose the war. If it establishes Weisselberg lied at the plea or at trial, it may help the Trump entities on trial, but then the judge could very well throw the book at Weisselberg at sentencing (which the court pointedly noted it could do if Weisselberg breaches any of the plea conditions) and he thereafter could easily flip on Trump. Thus, in spite of what appears to be bravado by the Trump organizations claiming on the day Weisselberg pleaded that they did nothing wrong, it is by no means clear they will go to trial, nor risk the damning daily drip of Trump-related financial shenanigans in the press just weeks before the midterms. In short, they too may decide to plead guilty.

On closer inspection, Bragg got even more from last week’s plea. Assuming Weisselberg is asked about Trump at the trial (a fair assumption since, among other reasons, the former president’s conduct can result in criminal liability for the Trump entities), it would be exceedingly difficult for Weisselberg to avoid implicating Trump. He would have to contend credibly that although Trump was a beneficiary of the tax scheme, and signed some of the pertinent checks, at no point during the 15-year scheme was Trump aware of any of the off-book executive compensation and that his companies and executives were not paying the necessary taxes on that compensation. In a small outfit like the Trump Organization, and with Trump’s penchant for micro-managing, that seems far-fetched. And as Weisselberg is represented by competent and ethical counsel, the DA can be assured they will strongly advise Weisselberg that he risks spending the remainder of his life in jail if he lies at the trial. That jail time will commence, by agreement of the parties, upon the conclusion of the October trial.

In addition to potentially gaining whatever evidence Weisselberg may provide about the former president at the upcoming trial, Bragg may well have something else up his sleeve to induce Weisselberg and others to cooperate fully, namely a whole new set of charges against Trump executives, including Weisselberg. 

The current indictment on its face seemed to augur such action: its description of the scheme implicates many more individuals than Weisselberg, as other executives were the personal beneficiaries of the very same scheme (the indictment, per established protocol, does not identify those individuals by name, as they were not charged at the time). So additional charges always seemed a strong possibility. A sign that that may finally be in the works is another unusual part of the bespoke agreement between Weisselberg and Bragg. A typical plea agreement in a situation like this provides some level of repose for a defendant — that is, protection that the prosecution won’t just turn around the next day and prosecute him for additional crimes. Thus, plea 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. Could the defense have taken the risk that no such charges would be forthcoming? For sure. But given what had to be the unwillingness of the DA to provide such protection, it is at least as likely that Bragg is awaiting the conclusion of the upcoming trial and Weisselberg’s incarceration on the current charges to bring a second set of charges. Bragg’s team could conclude that nothing would focus the mind of the 75-year-old Weisselberg like being incarcerated in Rikers and facing a whole new set of charges. Only time will tell, but if I were a betting man, that is what I would put my money on.

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Fairly or unfairly, Bragg, like Attorney General Merrick Garland, is going to be judged by history in how he handles this singular investigation. So far, like his federal counterpart, he has played it by the book. And he appears to have been at least as aggressive as Garland: after all, the scheme to which Weisselberg pleaded guilty involved both state and federal tax crimes, yet only Bragg has to date prosecuted those offenses — there is remarkably no sign, in spite of Weisselberg’s explicit admission that he violated federal tax laws, that he, the Trump companies, or any other executives are on the federal radar screen. 

Whether Bragg will continue to prosecute aggressively and fairly remains to be seen, but for now it is certainly worth reconsidering the initial judgment concerning his work. He may well be rising to the historic moment in which he finds himself, and demonstrating the backbone, temperament, and principles necessary to the task at hand.


Photo credit: Manhattan District Attorney Alvin L. Bragg, Jr. prepares for a press conference regarding Steven Lopez and the Central Park jogger case at New York State Supreme Court on July 25, 2022 in New York City (Michael M. Santiago/Getty Images)