Is Cy Vance Punting the Trump Investigation?

Photo-Illustration: Intelligencer. Photos: Getty Images

This week was supposed to mark the beginning of the end of an era in New York City crime fighting, with Alvin Bragg’s election on Tuesday to succeed Manhattan district attorney Cyrus Vance Jr. after his 12 years in office. For at least one person with a significant vested interest in the transition, the break won’t be as clean as he might have hoped: Donald Trump.

On Thursday, the Washington Post reported that Vance’s office had convened a new, “long-term grand jury to hear evidence about the Trump Organization’s financial practices,” thus further extending its investigation along with the corresponding uncertainty over the criminal exposure of Trump, whom the office has been investigating since 2019.

It’s hard to say exactly what this means since the investigation was supposed to be winding down by now. Back in late May, the Washington Post reported that Vance’s office had “recently” convened a special grand jury for a six-month term to investigate the Trump Organization, meaning the jury’s term is set to expire in a matter of weeks. Vance has also repeatedly said — as recently as late September — that his plan was to complete decisions about whom to charge in the investigation before he leaves office at the end of December.

Through much of the nearly two-and-a-half-year probe, it has seemed as if Vance might be building a case against Trump, but it has yet to materialize despite the hype. The investigation began in earnest when Vance’s office learned in July 2019 that federal prosecutors had concluded their own exploration of “hush money” payments Trump had made to Stormy Daniels during the 2016 presidential election. Shortly thereafter, Vance’s office subpoenaed records from the Trump Organization and Trump’s accounting firm, which were obtained this past February after some legal wrangling that went all the way to the Supreme Court. That same month, Vance recruited a veteran white-collar-crime lawyer to lead the investigation, and by May the office had opened the first special grand jury. Over the spring and summer, the office reportedly tried to persuade CFO Allen Weisselberg to cooperate against Trump, seemingly building momentum toward the prosecution of Trump himself, but the longtime lieutenant didn’t flip and was indicted along with the organization in July for alleged tax evasion on compensation from the company. The imminent expiration of the initial grand jury’s term — coupled with Vance’s departure from office shortly thereafter — seemed as though it would force some sort of final reckoning over Trump’s possible criminal liability in New York.

The Post’s story on Thursday puts a perhaps charitable gloss on the latest development, reporting that one “person familiar with the matter said the second grand jury was expected to examine how former president Donald Trump’s company valued its assets,” which “appears to be a separate issue than the one described in indictments from the first grand jury.” The suggestion that this might have been a deliberately planned phasing of the investigation — first the tax issues, now valuation issues — is difficult to reconcile with Vance’s repeated statements about his intention to complete it before the end of his term, as well as years’ worth of statements from the office and news reports about the scope and progress of the investigation.

The contours of Vance’s probe — and of Trump’s corresponding criminal exposure — have never been entirely clear, but the office and stories in the press have suggested at various points that the investigation already encompassed a variety of possible financial frauds regarding the value of Trump’s properties and assets based on potential misrepresentations to lenders, insurers, and tax authorities. Given this ostensibly broad scope, Vance’s investigation has seemed the most likely of all the ones concerning Trump — with the exception of the Mueller investigation — to ensnare the man himself. But it’s one thing to identify suspicious areas for inquiry, and it’s another thing entirely to actually investigate them, to identify more than just numerical discrepancies but material misrepresentations, to evaluate financial-reporting conventions that may be context- and industry-specific, and, beyond all that, to identify culpable individuals with fraudulent intent. The strong sense that Trump is a crook — that he has lied and cheated his way through life whenever possible — is no substitute for this work, which has meant, all along, that indicting Trump would be a far more complicated and improbable undertaking than most legal pundits have suggested.

It is far from clear what we should glean from the news of this second grand jury. Prosecutors have reportedly been considering whether to charge Matthew Calamari, the Trump Organization’s chief operating officer, with charges similar to those Weisselberg faces concerning tax evasion, but if the Post’s reporting is accurate, it would not make sense to impanel a second grand jury for this purpose alone. Prosecutors could seek an extension of the first grand jury’s term on the theory that its work is ongoing, though the jurors would have to vote in favor of such an extension and a court would need to approve it.

The distinction between these two scenarios — an extension of the first grand jury, as opposed to impaneling a new one — may seem negligible, but it matters in New York because prosecutors cannot admit hearsay before a grand jury. That means that if prosecutors want to charge someone in a second grand jury for conduct for which key witnesses provided testimony in the first grand jury, those witnesses would need to be called to testify again, and there would be a risk that they would provide inconsistent testimony — something that, in turn, would make them more susceptible to cross-examination at trial. This is one reason Daniel Alonso, the former chief assistant district attorney in Vance’s office, told me before the Post’s story on the new grand jury that it would be “far preferable to vote all charges before this grand jury expires.”

At the moment, there is little to provide in the way of reliable prognostication — and just enough information to fit a broad range of possibilities.

The one that may gain quickest traction among many anti-Trump legal observers is that a new grand jury may mean Vance’s prosecutors are onto something significant and may be preparing to charge more people for conduct unrelated to the tax shenanigans alleged in the pending indictment against Weisselberg and the Trump Organization — perhaps even Trump himself. That tantalizing scenario remains possible but is improbable, mostly because if a major development of the sort that has widely been regarded as a necessary precondition to charging Trump had come to pass (like the cooperation of Weisselberg or grand-jury testimony of another key insider), there’s a pretty good chance it would have been publicly reported. But nothing of consequence about the investigation has found its way into the public domain since Vance’s last significant comment on the investigation — just six weeks ago — when he reiterated his intention to complete it by the end of the year.

At the other end of the spectrum, Vance may have decided to let the prosecutors press forward with a focus on the asset-valuation issues despite any reason to believe a major breakthrough is close at hand. An uncharitable observer might call it a fishing expedition — or perhaps an unsporting decision on the part of Vance to avoid responsibility for a result that will disappoint many people in yet another closely watched Trump investigation that fails to result in charges against Trump himself. After all, Vance’s office has a checkered history with major white-collar investigations, and leaving the work to Bragg — who campaigned on dramatically increasing white-collar enforcement — is probably a more pleasant way to leave office than as the second much-heralded prosecutor to come up short against one of America’s worst human beings.

Meanwhile, Trump still faces other actual and possible criminal investigations of varying potency. The Westchester County District Attorney’s Office, now led by a former federal prosecutor who happens to have once been an anti-Trump cable-news legal commentator, recently opened an investigation that appears to concern possible misrepresentations to local officials about the property value of one of Trump’s golf clubs. The investigation of the district attorney in Fulton County, Georgia, concerning Trump’s possible effort to manipulate the state’s presidential-election results also remains ongoing, though there has been relatively little reporting indicating how advanced the inquiry is.

And, of course, it remains to be seen whether and to what extent the Department of Justice will open an investigation into Trump’s conduct concerning possible federal offenses resulting from his financial dealings and attempted election meddling — investigations that, on the merits, should already have been opened given the publicly available information. It is possible that Attorney General Merrick Garland already approved such an investigation at some point without its being publicly reported or that he may do so if newly uncovered facts eventually warrant it in the course of the investigation into the U.S. Capitol riot on January 6. Either scenario seems unlikely given President Biden’s and Garland’s own apparent concerns about the politically divisive consequences of a federal investigation into Trump’s conduct, as well as Garland’s evident aspiration — however improbable in reality — to be a historic, unifying figure of bipartisan national appeal. A probe by the Justice Department would probably also be even more publicly controversial now than it would have been when Garland took office eight months ago, and it may only get more contentious as time passes, particularly if Trump announces his candidacy for 2024.

All of that suggests, for better or worse, that Bragg is now about to become one of the country’s most closely watched and consequential criminal prosecutors.

Is Cy Vance Punting the Trump Investigation?