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N.Y. grand jury said to return criminal indictments against Trump’s company and its CFO, the first from prosecutors probing the former president’s business dealings

Former president Donald Trump leaves Trump Tower in Manhattan on June 15. (Jeenah Moon for The Washington Post)

NEW YORK — A grand jury in Manhattan filed criminal indictments Wednesday against former president Donald Trump's company and its longtime chief financial officer, according to two people familiar with the indictments.

The indictments against the Trump Organization and its CFO, Allen Weisselberg, will remain sealed until Thursday afternoon, leaving the specific charges against them unclear. Earlier Wednesday, people familiar with the case said the charges were related to allegations of unpaid taxes on benefits for Trump Organization executives.

Weisselberg is expected to surrender Thursday morning at the office of Manhattan District Attorney Cyrus R. Vance Jr. (D), two people familiar with the plan said. He is expected to be arraigned later in the day in front of a state court judge. The Trump Organization will also be arraigned, represented in court by one of its attorneys.

The criminal charges against the Trump Organization and Weisselberg are the first to result from the investigations by Vance and New York Attorney General Letitia James (D) and represent a dramatic turn in the long-running probes.

Attorneys for both the Trump Organization and Weisselberg declined to comment Wednesday.

During an interview Wednesday night with Fox News’s Sean Hannity, Trump called the myriad investigations — and, earlier, impeachments — of him “all nonsense.”

“New York radical left prosecutors come after me — you gotta fight,” he said.

Spokespeople for Vance and James — who teamed up to investigate Trump’s business dealings this year after years of working on separate tracks — also declined to comment.

On Wednesday afternoon, Vance was seen heading into the lower Manhattan building where the grand jury sits three days a week, accompanied by Carey Dunne, the office’s general counsel and one of the most senior attorneys on the prosecution team. Vance left the building nearly three hours later with a member of his security detail. He did not respond to a question from a reporter as he left his office for the day later Wednesday.

The people familiar with the indictments spoke on the condition of anonymity to disclose private actions.

Trump himself is not expected to be charged this week, the people said, and no others in his orbit are expected to face imminent charges. But the indictments could mark a significant escalation in his legal problems — both by exposing his company to potential fines and by raising the pressure on Weisselberg. Prosecutors hope Weisselberg will offer testimony against Trump in exchange for lessening his own risk, according to another person familiar with the case.

Weisselberg, who has worked for Trump since the 1980s, is considered the most important figure in the Trump Organization who is not related to Trump. He has been involved in even minor financial transactions, including coordinating Trump’s personal gifts to charity.

The Washington Post has previously reported that Weisselberg was a key figure in the investigations by Vance and James. Both are trying to determine whether Trump broke the law by misleading lenders or taxing authorities, or by evading taxes on forgiven debts or fringe benefits for employees, according to court papers and people familiar with the cases.

In recent months, both sets of investigators have spoken to Jennifer Weisselberg, the CFO’s former daughter-in-law, who said that Weisselberg’s son Barry had been given a free apartment and a hefty salary while he worked at the Trump Organization’s Central Park ice rink. Prosecutors were looking into whether taxes were paid on the benefits, people close to investigation said.

The twin, and now merged, investigations of Trump’s company appear to be the longest-lasting and widest-ranging probes ever undertaken into the Trump Organization.

Both investigations appear to have been set in motion by an unlikely figure: Michael Cohen, who spent years as Trump’s attorney and aggressive defender. But Cohen turned on Trump in 2018 after coming under investigation himself. Cohen later pleaded guilty to making hush-money payments during the 2016 presidential campaign to women who said they’d had affairs with Trump years before.

Vance’s office opened an investigation in 2018, responding to Cohen’s charges that Trump had directed the illegal payoffs. But Vance’s probe broadened beyond those allegations to encompass years of business transactions. Vance examined tax breaks Trump got on an estate in suburban New York, loans Trump took out on his Chicago tower, and statements Trump made to New York tax authorities about the value of his Manhattan towers, according to previous court filings.

The investigation became bogged down for much of Trump’s term, however, because of a long legal fight over his tax returns. Vance had sought them from Trump’s accountants in 2019, but Trump sued to stop him, saying that — as president — he was immune from investigation by any state-level prosecutor.

The case went to the Supreme Court twice; Trump lost both times. But Vance did not obtain Trump’s returns and other financial records — a cache including millions of pages of documents — until February 2021, after Trump had left office.

Now, the indictment sets up an unprecedented legal showdown between prosecutors in Manhattan and a powerful former president with an enduring grip on the Republican Party. Vance has said he will not seek reelection this year. That means the bulk of the case against Trump’s company could be handled by Vance’s successor.

Trump and his organization have never faced criminal charges, but he has been the target of civil lawsuits from the office of the New York attorney general. In one case, he was sued for allegedly defrauding students at Trump University. That case and others against Trump University ended with Trump paying a $25 million settlement in 2016. And in 2018, Trump was sued for misusing money in a charity he controlled, a case that resulted in a judge ordering Trump to pay $2 million in damages.