If Trump’s a Tax Cheat, His Criminal Reckoning Has Finally Arrived

Prosecutors finally won the fierce battle to get his tax returns and reams of financial records. Here’s what comes next.
February 25, 2021, 8:22pm
Bill Christeson holds up a sign that reads "Follow the Money" outside the Supreme Court, Thursday, July 9, 2020, in Washington.
Bill Christeson holds up a sign that reads "Follow the Money" outside the Supreme Court, Thursday, July 9, 2020, in Washington. (AP Photo/Andrew Harnik)

Prosecutors’ stunning victory in their long-running quest for Donald Trump’s tax returns brings them to a new challenge in the historic criminal investigation of the ex-president: determining what those documents actually prove.

The Manhattan District Attorney’s office finally obtained Trump’s financial records on Monday after over a year of courtroom battles, which reached all the way to the Supreme Court, a spokesman for the prosecutor’s office told VICE News Thursday. The documents reportedly add up to millions of pages

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The delivery of Trump’s inner-most private records to an aggressive criminal prosecutor marks the dawn of a new era in the long-running investigation into Trump’s secretive financial empire. Trump now faces a level of criminal jeopardy that appears unmatched by any former president in U.S. history. And the handover of his tax returns removes a key stumbling block that has delayed the investigation for over a year.

Prosecutors’ massive new task is to figure out whether the reams of records support an airtight case against the former president. 

Doing that may be tricky, experienced prosecutors say, even if some of the facts at hand appear damning at a surface level. White-collar criminal cases can be immensely complicated, and the vast trove of documents could take months to sift through. 

“Even if there is wrongdoing, these cases are very hard to prove,” said Rebecca Roiphe, a former New York prosecutor and an expert on prosecutorial ethics at New York Law School. “While public reporting already shows a great deal of concerning information, it does not clearly establish a crime.”

Trump’s estranged former attorney Michael Cohen has testified that Trump’s company fiddled with the valuations of Trump’s assets to obtain favorable terms for loans and insurance coverage, or to reduce real estate taxes. If so, that could represent bank fraud, insurance fraud or tax fraud. 

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Trump and his company have denied wrongdoing, and blasted the investigation as a politically-motivated witch hunt. 

“For more than two years, New York City has been looking at almost every transaction I’ve ever done, including seeking tax returns which were done by among the biggest and most prestigious law and accounting firms in the U.S.,” Trump said in a statement earlier this week after the Supreme Court denied his final last-ditch effort to shield his records. “This is something which has never happened to a president before. It is all Democrat-inspired in a totally Democrat location, New York City and State.”  

The reams of tax documents and other financial records may finally provide the documentation necessary to back up Cohen’s claims.  

On the other hand, the records by themselves might not be enough to support a case. Experienced prosecutors say the subject of a complex financial investigation can be insulated from provable wrongdoing by layers of accountants, lawyers, advisors and other go-betweens. Even if the files show that a crime occurred, they may not conclusively link the head of the company—in this case, Trump—to any wrongdoing.  

That means prosecutors may need to rely on the testimony of witnesses to ascertain what kind of instructions Trump issued to others. They might prove reluctant to testify, even in the face of pressure from prosecutors. In Trump’s tight-knit family business, key witnesses might include Trump’s own adult children—Don Jr., Eric, and Ivanka.

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“It is very hard to prove intent in these sorts of cases,” Roiphe said. “Bank and insurance fraud would also be difficult to prove because valuing real estate assets involves a great deal of guesswork, which will make it hard to show that Trump or his organization intended to commit fraud.”

There are several signs that Manhattan District Attorney Cy Vance’s investigation has accelerated ever since Trump lost his bid for reelection on November 3, while adding resources that could help him meet these challenges. 


Vance’s team hired a well-known white-collar criminal expert named Mark Pomerantz in February, reportedly to bolster the team scrutinizing Trump’s family business. His office subpoenaed records relating to Trump’s Seven Springs estate north of New York in December, and hired a team of forensic accountants known as FTI Consulting, which can bring high-end artificial intelligence capabilities to the process of digging through the huge pile of records. 

The new stage of the investigation will involve crunching the numbers, comparing documents that were submitted to various institutions, and attempting to ascertain the motivations of key players like Trump and his longtime chief financial officer, Allen Weisselberg. 

But now that their key battle to crack open Trump’s secretive financial empire has been won, the investigation shifts—from prying loose Trump’s most tightly-guarded documents to the question of what those documents can actually prove.