Now that the first indictment has been filed in New York’s investigation of former president Donald Trump and his businesses, debate is raging about what it means for the man whose name appears on virtually every page, but who was not himself charged. As criminal law experts who have handled white-collar cases for decades, our view is that the indictment portends a series of escalating risks for the former president — risks that increase the likelihood of his eventual prosecution.

 

Far from the penny-ante charges some expected, the indictment revealed by Manhattan District Attorney Cyrus Vance Jr. lays out a sweeping 15-year conspiracy to commit tax evasion and other frauds. It charges 15 felonies in total against the defendants: Trump’s businesses, including the Trump Organization, and its chief financial officer, Allen Weisselberg. Weisselberg is alleged to have been paid more than $1.76 million “off the books,” along with other executives who allegedly also received untaxed income “through indirect and disguised means.” The defendants face substantial financial penalties and, in the case of Weisselberg, up to 15 years in jail (although as a first-time offender, a court may sentence him much more leniently if he’s convicted).

Trump may not have been formally charged, but make no mistake: This initial case is an indictment of how he did business at the company that bears his name, that he ran for almost five decades and that he reportedly micromanaged. Even with his damaged reputation, the indictment tarnishes further the once-gilded Trump brand.

Nor is this a fleeting reputational hit. Clearly, the prosecutors are prepared to go to trial. The charging document is brimming with (evidently well-documented) details about alleged tax-free compensation secretly paid through the instrumentalities of Manhattan apartments, Mercedes-Benz vehicles and private-school tuition — the fruits of the district attorney’s years-long battle to obtain the Trump Organization’s financial records. Such tales of greed and corruption typically do not sit well with juries.

Even if no further charges are ever filed, the case means Trump’s name and brand will be a constant target of negative publicity for many months or even years ahead. That will include pretrial proceedings and motion practice, a highly publicized trial and, perhaps, post-trial and appellate proceedings — all of which probably will be accompanied by the same media frenzy we saw this week.

But the imminent risks to Trump hardly stop there. The Trump Organization already was reported to rest on shaky financial ground even before the indictment. In 2020 alone, Trump’s hotels, resorts and other properties were reported to have lost more than $120 million, and he personally has guaranteed more than $400 million in outstanding debt, much of which is soon to come due. Questions had been raised as to whether Trump would have the wherewithal to make those payments even before this additional reputational torpedo.

Any effort to salvage the business just got a lot more complicated because of the sheer distraction factor occasioned by the legal proceedings. Weisselberg, the principal financial manager of the Trump Organization for decades, looked understandably shellshocked as he appeared in court Thursday: He is facing an array of charges that could destroy him and his family financially and land him in jail. He probably will find it hard to concentrate on the day-to-day responsibilities of keeping the company afloat.

Criminal charges also can have devastating collateral effects on companies. The prosecution in the Enron affair of the Arthur Anderson accounting firm famously destroyed it, even though the conviction eventually was reversed by the Supreme Court. Companies can have debt covenants that are triggered by criminal convictions, or by evidence of wrongdoing such as the mere failure to maintain honest books and records. The complaint against Trump’s business alleges bookkeeping failures in painstaking detail. Even though Trump’s main lender, Deutsche Bank, reportedly has decided it will not call the loans, who knows what the future holds.

Those are just the harms that may transpire even if no further charges are brought. But as we explain in a new report about the investigation, we believe that Trump himself remains at risk of being charged as the investigation progresses.

The indictment takes pains to portray the scheme to defraud as pervasive, to make clear that a number of executives benefited from it, and to describe Weisselberg as “one of the largest beneficiaries of the scheme” — raising the question of who else might have benefited as much as the company’s second-in-command. Prosecutors already have announced that their investigation is ongoing, and apparently have not ruled out charging the ex-president. When asked by defense lawyers whether Trump would be included in the indictment, government lawyers reportedly answered, “not now.”

Investigators have been probing a number of the Trump Organization’s other allegedly dubious practices in addition to this week’s charges. In what is surely no coincidence, the indictment maps closely onto those other issues. They seem to be establishing the scaffolding on which they could hang other related charges if borne out by the developing evidence.

For example, the indictment charges tax fraud for fringe benefits; prosecutors reportedly are looking at other possible tax frauds, such as the handling of consulting fees (some paid to the Trump family), conservation easements, “debt parking” and other questioned tax practices.

To take another example, the indictment charges the maintenance of false records in connection with fringe benefits; prosecutors reportedly also have been looking at whether the Trump Organization also maintained two sets of inconsistent records for its properties, inflating the numbers to get loans and insurance, and deflating them for tax purposes. (The alleged concealment of hush money payments to Trump’s mistresses that kicked off the New York investigation also could be charged as a falsification of records offense; the repayments reportedly were accounted for by the company as “legal expenses.”)

And a third example: The indictment charges a fringe benefit scheme to defraud the government; prosecutors also reportedly have been scrutinizing other schemes to defraud in the context of insurance and lender fraud.

And on and on. These examples suggest a recurring pattern of alleged practices that (if proved) cohere with the structure of the scheme to defraud that prosecutors have already charged. The prosecutors are laying the foundation. Now they may well build on it — if the evidence merits it.

We disagree with those who draw conclusions of impunity from the fact that broader charges were not immediately included in the first case. As lawyers who have worked on large financial fraud and other white-collar cases, we know that it is not unusual in complex investigations for initial charges to be followed by later ones. Superseding indictments often are filed as new proof is unearthed and as defendants cooperate and provide evidence that incriminates co-conspirators. In the Mueller investigation, for example, 34 people and three companies were ultimately indicted or pleaded guilty to more than 100 charges of wrongdoing over a period of nearly a year after the initial case was filed.

To be clear, we don’t know — and prosecutors presumably do not yet have sufficient proof to allege — that Trump or his associates acted with the intent to defraud in these other matters beyond fringe benefits. Such evidence is required to charge Trump or others under New York law.

 
 

That is where Weisselberg might come in. With an individual like Trump who entirely avoided email communications — which often are introduced as Exhibit A in any prosecution — a live witness is needed to testify about conversations, corrupt agreements and other proof of a culpable state of mind. Weisselberg may have resisted cooperating so far, but that was before Thursday’s litany of charges were filed. The world changed for him this week as images of his handcuffed “perp walk” were broadcast around the world.

We each have prosecuted or represented defendants who “flipped” in response to pressure like the CFO now faces. We have seen far more hardened individuals than this 73-year-old accountant decide to cooperate under the financial and existential strain of criminal charges (not to mention the specter that his son might also be charged, as the indictment not so subtly intimated is possible). It is premature to rule out cooperation now just because Weisselberg did not cooperate before he was indicted.

If Weisselberg does cooperate, or if other cooperators materialize, there will be substantial defenses available to Trump — but there also are substantial responses to them. Take, for example, the statute of limitations. Most felonies in New York (and all of those in the indictment) have a five-year statute of limitations, meaning that charges must generally be brought no later than five years after the criminal act was committed. This indictment was returned on June 30, 2021, so any charged criminal conduct would need to have occurred on or after July 1, 2016. If strictly applied, that would exclude large swaths of the conduct alleged in this week’s indictment, and of the additional conduct reportedly under investigation.

But the problem for Weisselberg, the Trump Organization and other potential defendants, including Trump himself, is that a broader conspiracy charge allows earlier criminal acts to be charged as part of an ongoing offense that stretches into the period that remains within the statute of limitations. The first indictment did just that. It is a common approach that courts regularly permit. Other defenses we cover at length in our report also have similar possible rejoinders.

For all these reasons, looking at the public facts we do have and applying the law to them, we believe Trump remains at risk of indictment. That is not to say he will necessarily be charged. Assessing present risk is not the same as predicting future investigative outcomes, and there are unique questions to weigh in deciding to file criminal charges against a former president who hasn’t ruled out running for another term. Nor do we have all the evidence — although we have more to work with now that the first charges are on record. But the facts we do have, the patterns they suggest, the determination of the prosecutors and the pressure on Weisselberg are all ominous for Trump.

To paraphrase Winston Churchill, this indictment is not the end of Trump’s legal troubles. It is probably not even the beginning of the end. But it may be the end of the beginning.