The Problem With Prosecutor Punditry

Experts keep promising the walls are closing in on Trump. Haven’t we learned anything?

Photo-Illustration: Intelligencer. Photos: Getty Images
Photo-Illustration: Intelligencer. Photos: Getty Images

You could be forgiven if you experienced a vague sense of bewilderment after the Trump Organization and Allen Weisselberg were charged, depending on what you were reading and watching in the days that preceded it.

Just that week, some prominent legal commentators had suggested that Trump himself might be charged (despite days of reporting indicating otherwise), that the charges would extend beyond the tax-fraud scheme that is reportedly at issue (and ultimately alleged), or that the Trump Organization would quickly go under if charged (which remains to be seen). In retrospect, this was not all that surprising: Similar claims had been swirling around in the media to varying degrees ever since a series of developments in late May suggested the investigations in New York were picking up steam.

The actual charges filed by the Manhattan district attorney’s office are undoubtedly serious, but it is far from clear what will happen next, which has prompted a range of reactions among the legal commentariat that seem to differ more on points of emphasis, tone, and probability, than on the ultimate danger to Trump. Some have been circumspect, others more adventurous. Immediately after the filing, one prominent legal pundit confidently told The New Yorker, “They are on the precipice. They are on the brink of a much larger case against Trump and his businesses.” Another contemplated a domino effect extending beyond just the Manhattan DA, with a potential future charge against Trump opening “the floodgates for other prosecutors’ offices to wade into the Trump-indictment pool.” A former litigator for the New York attorney general’s office argued for the Washington Post that the widespread interest in Weisselberg’s potential as a cooperator against Trump was misplaced — that a case could largely be built simply on documents — and offered that he had “helped lead” the office’s civil lawsuit against Trump University (something he called a “civil prosecution,” which is not a thing).

All of this feels uncomfortably similar to the sorts of analyses and predictions made among professional legal prognosticators that we heard throughout the Trump presidency. There is an insatiable demand in the media and among the public for detractors of Trump, including those who come with the built-in credibility and experience with the criminal-justice system that former prosecutors can offer. But over the course of the Trump administration, the results of all this legal commentating were, in the main, decidedly mixed — and often a disappointment for people who expected Trump to face some dramatic legal reckoning at the hands of prosecutors during his term. Often, pundits offered analysis that distorted the public’s sense of how the criminal-justice system really works and flattered the audience’s prejudices by suggesting that serious legal consequences for Trump might be just around the corner.

There was, after all, plenty to talk about during the Trump presidency. For decades, Trump has basically toed the lines of legality and sometimes crossed them: He settled the Trump University fraud case, and his charitable foundation was found to be engaged in illegal self-dealing, which led it to get the civil death penalty. The New York Times has documented how he built his fortune on what looks, at least in part, like fraud. In the White House, he abused his powers in countless ways, leading to two impeachments. And that’s to say nothing of his cronies, many of whom were convicted and sent to prison, or of a Justice Department that generated more scrutiny and controversy than any other in modern history.

To make sense of it all, a slew of former Justice Department officials and government lawyers became media personalities. I am also a former federal prosecutor who has been sharply critical of Trump and former attorney general Bill Barr, perhaps overstating matters on occasion. It is an inherently awkward position: As a prosecutor, you do your best to be meticulous and careful, understanding that a misstep or a stray word here or there can screw up a case, and if you have ever had a case covered by the press, you have no doubt gone crazy over some aspect of the coverage that you thought missed the point of your case, misconstrued one of your arguments, or failed to appreciate that you might know something the public does not. Once you enter the media space as a legal commentator, you become, on some level, part of the problem you once bristled at — speaking with limited insight and being asked to speculate about cases you do not know from the inside — while, in theory, doing your best to offer the public some insight into our often opaque legal system.

It wasn’t all bad. Some commentators — like former Manhattan U.S. Attorney Preet Bharara and former U.S. Attorney Joyce White Vance, who appear on CNN and MSNBC, respectively — tend to be more cautious in their assessments and are frequently insightful. (Vance co-hosts a podcast with Bharara for Cafe Studios, which was recently acquired by New York’s parent company, Vox Media.) Former acting solicitor general Neal Katyal (MSNBC) writes admirably lucid op-eds, and former Manhattan federal prosecutor Elie Honig (CNN and Cafe) has an appealing plainspokenness and an ability to convey complex legal concepts in simple terms that is rare among serious lawyers. Given that the so-called elite legal profession is overwhelmingly dominated by white men, it is also refreshing to see people like Vance, Bharara, and Katyal in the ranks of prominent on-air personalities.

But no one is immune to the incentives of Twitter-amplified cable stardom, which rewards clear and confident opinions, snap judgments, and dramatic predictions. Indeed, they seem to converge in a particularly problematic way with the nature of the profession itself. As lawyers, we are trained to be assertive, to argue with confidence, and to shape facts into coherent narratives, but legal commentators are encouraged to use their professional skills as advocates rather than analysts and to oversimplify otherwise complex legal and factual issues. The job of a lawyer is fundamentally about trying to reduce ambiguity in the world — whether for a judge in an argument, a jury in a trial, or a client who needs advice — but the law is not always clear-cut, and it is difficult to render confident judgments with incomplete information, which is almost always the case in a criminal investigation, especially from the outside.

Recall, for instance, that brief moment in summer 2018 when it seemed as if Trump might finally face the music after Michael Cohen pleaded guilty to paying hush money to Stormy Daniels to bury her claims of an affair with Trump in the run-up to the 2016 election, which Cohen said he had done in coordination with Trump. It was a legitimate bombshell — the president’s onetime lawyer had confessed to crimes that directly implicated Trump — and to many legal pundits, Cohen’s claim seemed to establish a criminal case against him. “We can say without exaggeration that if Donald Trump was not currently president of the United States, he would be under indictment or he would be imminently under indictment,” said Susan Hennessey, a former attorney at the National Security Agency who was then a CNN regular. Weeks before last November’s election, Vance and her fellow former U.S. Attorney Barbara McQuade (a New York contributor) wrote, “It appears that the Justice Department has already reached the conclusion that there is sufficient evidence to charge Trump.” After the election, George Conway — a onetime contender for a senior position at the Trump DOJ who went on to become a Never Trump figure — argued that the Justice Department had “in effect, already determined that Trump committed” the crime based on Cohen’s plea.

In February, however, the Associated Press reported that the investigation was “dead,” with no charges to be brought against Trump, and there is no indication the Biden administration will reopen it. This likely has something to do with the fact that a case built largely on the word of Cohen — a notorious liar who did not fully cooperate with prosecutors — would be very risky. Another problem is that a criminal prosecution based on violations of campaign-finance law requires the government to prove the defendant knew his conduct was unlawful, and Cohen could not by himself establish that on the part of Trump, a problem that may similarly complicate Weisselberg’s potential utility as a cooperator against Trump in the pending tax-fraud case.

This dissonance between the confidence in Trump’s criminal exposure expressed by commentators and its reality was conspicuous throughout the Mueller investigation, which proved to be ratings gold for cable news and an incomparable star-making vehicle for lawyers. Mueller’s secretive two-year probe into the Trump campaign and Russian election interference was punctuated by legitimate bombshell developments, and its progression lent itself to endless on-air speculation, as when legal analysts argued that Paul Manafort’s indictment meant that Mueller was “quite likely on the verge of handing down new major indictments” or that, after Manafort’s conviction, there was a good chance he would finally flip on Trump. Hennessey in particular has been called to the carpet since getting a job in the Biden Justice Department. Most of the hand-wringing was over the top, but for those of us who watched in real time, it was hard to argue with the assessment, contained in a critical National Review article, that she had “repeatedly suggested that [Mueller’s] findings would spell disaster for the Trump White House” — even if the same could be said about pretty much every legal analyst on CNN and MSNBC at the time.

On some level, you could forgive them for being uncharitable to Trump in their prognostications about a possible conspiracy or so-called collusion between his campaign and Russia given the unprecedented contacts between the two, to say nothing of the endless dissembling and Trump’s publicly known efforts to stop the investigation. But of course, the whole thing resolved itself in a remarkable anticlimax: no conspiracy and no determination on the colloquial “collusion,” a mostly unreadable report, and many confused viewers. No wonder there was such a letdown when Mueller’s report was finally released, considering the years-long, wall-to-wall hype that preceded it.

Taking Mueller’s place in the expectations game has been Cyrus Vance, the Manhattan D.A. investigating the Trump Organization’s business practices. As New York previously reported, the investigation has led many legal experts who have followed the stories about the questionable financial dealings of Trump and his business to believe that he “could become the first former president in American history to find himself on trial — and perhaps even behind bars.” When Vance’s office obtained Trump-related financial records from Deutsche Bank last August, some members of the legal punditocracy appeared to suggest that a prosecution could follow simply by comparing the bank’s records to documents from Trump’s accounting firm.

You could chalk it up to the professional hazards of Twitter — shorthand is both its great draw and its considerable downside — but the problems extend beyond the platform. Katyal, who often seems to demonstrate the way cable-news punditry can lead even the best lawyers to take their analyses a crucial half-step too far, suggested on MSNBC last August that charges could come even before the election. (He also argued on MSNBC in mid-November that Trump’s “postelection behavior basically guarantees” a criminal prosecution, and in January he began his assessment of Trump’s call with Georgia’s secretary of state by saying Trump had “absolutely” committed a crime, even though most responsible prosecutors would want to develop some evidence of Trump’s mental state before reaching that conclusion.) Harry Litman, a former senior Justice Department official, argued in his Los Angeles Times column last November that Vance was “likely to reach charging decisions within a few months,” and in January, he said it “would be easy” for Vance to prove a fraud case. When Litman went on MSNBC in late May to talk about a Politico article that claimed Vance could be considering a criminal charge that Trump’s “business empire was a corrupt enterprise” under a law similar to the federal RICO statute, he cheerfully endorsed the theory. All of this considerably oversimplified how such cases actually work: Complex financial-fraud cases are among the most challenging investigations that prosecutors undertake, and, as I can attest from my own experience, they can be time consuming, byzantine, and frequently unsatisfying in their ultimate reach.

The Weisselberg and Trump Organization prosecution itself appears to reflect these challenges. The indictment alleges that, in “certain years,” there were effectively two sets of internal books at the Trump Organization — a general ledger as well as a separate set of internal spreadsheets that tracked the compensation to Weisselberg that is at issue — and that Weisselberg had “directed a staff member in the accounting department to remove the notations ‘Per Allen Weisselberg’” from the entries for some of the payments in the general ledger. CNN has reported that the company’s controller, Jeff McConney, testified before the grand jury, which likely means he received transactional immunity and will be a witness against Weisselberg. If accurate, that would give prosecutors both probative documentary evidence and an inside cooperator who could serve in a crucial narrative capacity for the jury.

For the moment, it is unclear whether Cyrus Vance’s office has — or will be able to develop — a similar body of evidence against Trump, either as part of the charged Weisselberg tax fraud or as a case based on the other sorts of possible tax, insurance, or bank frauds that have been posited in media reports. Any serious charges would likely require establishing, at a minimum, that Trump had intentionally been involved in the fraudulent scheme. And although establishing that sort of intent is frequently difficult, it is likely to be even more of a challenge with someone who reportedly does not use email and whose proximity to the details of the work being conducted under him seems at best unpredictable — and often strategically distant. This is not to say that amassing a critical mass of evidence against Trump (if, in fact, he did commit a crime) would be impossible, and Weisselberg’s cooperation could be crucial in that regard. But we simply do not know whether Trump will ever be charged, much less whether he may one day wind up in prison. Thus far, Weisselberg’s lawyers have said that he will “fight these charges in court,” but that could very well change at some point. 

An underlying paradox has been difficult for legal commentators to manage, both at the specific level of Vance’s office’s investigation and more generally: In charging Trump’s namesake company as well as a longtime senior executive, Vance has perhaps come closer than anyone — including both Mueller and the Southern District of New York — to Trump himself, and there is a nontrivial chance that Trump will one day personally be charged. You could put the odds at something like 10 percent, which may seem remote but is legitimately shocking considering we are talking about the former president of the United States.

There is also an undeniable moral component that is hard to fully extricate from the legal analysis. Trump is certainly a crook, if not (ultimately) a criminal. Throughout his personal and business life, he has left behind a trail of wreckage as few others have, and he has been the beneficiary of a culture of elite impunity and a legal system that favors the rich and powerful — people who can use their wealth and their connections to avoid serious scrutiny and, perhaps, indictment. He was also a catastrophically bad president whose corruption, incompetence, and solipsism caused roughly 600,000 American deaths (and counting) and an unprecedented siege on the U.S. Capitol. It is hard to imagine anyone more deserving of a serious legal comeuppance.

But for reasons both good and bad, the criminal-justice system is deeply imperfect and often unsatisfying. The existence of an investigation — irrespective of how many breaking-news segments it generates — does not mean a prosecution will (or even should) follow. Nor does it mean the walls are inexorably closing in on any given person at any point, no matter how despicable or deserving of justice he may be.

The Problem With Prosecutor Punditry