An indictment of the Trump Organization could mark the first criminal charges to emerge from an investigation by the Manhattan district attorney into Donald J. Trump and his business dealings.
The Manhattan district attorney’s office has informed Donald J. Trump’s lawyers that it is considering criminal charges against his family business, the Trump Organization, in connection with fringe benefits the company awarded a top executive, according to several people with knowledge of the matter.
The prosecutors had been building a case for months against the executive, Allen H. Weisselberg, as part of an effort to pressure him to cooperate with a broader inquiry into Mr. Trump’s business dealings. But it was not previously known that the Trump Organization also might face charges.
If the case moves ahead, the district attorney, Cyrus R. Vance Jr., could announce charges as soon as next week, the people said. Mr. Vance’s prosecutors have been conducting the investigation along with lawyers from the office of the New York State attorney general, Letitia James.
Any indictment would be the first to emerge from the long-running investigation and would raise the startling prospect of a former president having to defend the company he founded, and has run for decades, against accusations of criminal behavior.
Prosecutors recently have focused much of their investigation into the perks Mr. Trump and the company doled out to Mr. Weisselberg and other executives, including tens of thousands of dollars in private school tuition for one of Mr. Weisselberg’s grandchildren, as well as rents on apartments and car leases.
They are looking into whether those benefits were properly recorded in the company’s ledgers and whether taxes were paid on them, The New York Times has reported.
Mr. Trump’s lawyers met on Thursday with senior prosecutors in the district attorney’s office in hopes of persuading them to abandon any plan to charge the company, according to several people familiar with the meeting. Such meetings are routine in white-collar criminal investigations, and it is unclear whether the prosecutors have made a final decision on whether to charge the Trump Organization, which has long denied wrongdoing.
“In my more than 50 years of practice, never before have I seen a district attorney’s office target a company over employee compensation or fringe benefits,” said Ronald P. Fischetti, a personal lawyer for Mr. Trump. “It’s ridiculous and outrageous.”
Several lawyers who specialize in tax rules have told The New York Times that it would be highly unusual to indict a company just for failing to pay taxes on fringe benefits. None of them could cite any recent example, noting that many companies provide their employees with benefits like company cars.
Still, an indictment of Mr. Trump’s company could deal a blow to the former president just as he has started to hold rallies and flirt with a return to politics. The Trump Organization is inseparable from Mr. Trump, acting as the corporate umbrella for a portfolio of hotels, golf clubs and other real estate, most of which are branded with his name.
It is unclear whether Mr. Trump will ultimately face charges himself. The investigation, which began three years ago, has been wide-ranging, examining whether the Trump Organization manipulated the value of its properties to obtain favorable loans and tax benefits, people with knowledge of the matter have said.
The inquiry is also examining the organization’s statements to insurance companies about the value of various assets and any role that its employees — including Mr. Weisselberg — may have played in hush-money payments to two women during the 2016 presidential campaign.
Mr. Trump has derided the investigation by Mr. Vance, a Democrat, as a politically motivated “witch hunt.” He unsuccessfully tried to fight a subpoena from Mr. Vance’s office seeking eight years of his personal and corporate tax returns, a fight that twice reached the United States Supreme Court.
A spokesman for the district attorney’s office declined to comment on Friday. A lawyer for Mr. Weisselberg, Mary E. Mulligan, also declined to comment. A spokeswoman for the Trump Organization did not respond to a request for comment.
The meeting on Thursday between Mr. Trump’s lawyers and the prosecutors, held on a video call and lasting more than an hour and a half, was arranged by Mr. Fischetti, the people familiar with the meeting said. He is a former law partner of Mark F. Pomerantz, a former federal prosecutor and defense lawyer whom the district attorney’s office enlisted to help lead the inquiry into Mr. Trump and his business.
At least one representative of the New York attorney general’s office also attended the meeting, one of the people said. Ms. James’s office had been conducting a civil inquiry into some of the same issues that the district attorney’s office is examining, but joined Mr. Vance’s criminal investigation in recent weeks.
In the coming days, Mr. Trump’s lawyers plan to continue to try to persuade prosecutors not to charge the company, according to a person briefed on the matter.
Companies, even private ones like the Trump Organization, are subject to criminal prosecution, and can face fines and other penalties if they are found guilty. Charges also can threaten an organization’s relationships with banks and business partners and cause lasting reputational damage.
The indictments could increase pressure to cooperate on Mr. Weisselberg, who could seek to cut a deal with prosecutors to testify against Mr. Trump in exchange for leniency.
Mr. Weisselberg’s intimate knowledge of the Trump Organization — he has worked at the company for decades and was one of the top executives when Mr. Trump was in the White House — would make his cooperation an enormous asset to investigators looking at all aspects of the company. Because of that, he has been a central focus of scrutiny in the district attorney’s investigation, with particular attention paid to the benefits that he and his family received.
In general, those types of benefits are taxable, although there are some exceptions, and the rules can be murky.
Mr. Trump depends heavily on Mr. Weisselberg, who has continued to work at the Trump Organization while under investigation. In his book “Think Like a Billionaire,” Mr. Trump credited Mr. Weisselberg for doing “whatever was necessary to protect the bottom line.”
And few things grate at Mr. Trump like the prospect of disloyalty. Close allies have turned on him in the past, including his former personal lawyer and fixer, Michael D. Cohen, whom Mr. Trump has labeled a “rat.”
Mr. Cohen, who pleaded guilty to federal charges related to hush money payments to two women who said they had romantic affairs with Mr. Trump, is cooperating with the Manhattan district attorney’s investigation. After pleading guilty, Mr. Cohen said that it was Mr. Weisselberg who had helped the Trump Organization to disguise the reimbursements that Mr. Cohen received for paying off one of the women.
Mr. Weisselberg was not accused of any wrongdoing by federal prosecutors, and Mr. Trump did not pardon him in his final days in office, though he was said to have considered doing so. (A pardon would not have given Mr. Weisselberg immunity from state charges.)
After Mr. Cohen pleaded guilty in 2018, Mr. Trump expressed confidence that Mr. Weisselberg had not turned on him.
“One hundred percent he didn’t,” Mr. Trump told reporters for Bloomberg. “He’s a wonderful guy.”
Mr. Weisselberg is, in certain respects, the polar opposite of his longtime boss. Discreet and unassuming, the financial chief has avoided attention even as he has brought his family into Mr. Trump’s orbit. One of his sons, Barry, was the property manager of Trump Wollman Rink in Central Park. Another, Jack, works at Ladder Capital, one of Mr. Trump’s lenders.
But Mr. Weisselberg has done his part to contribute to Mr. Trump’s aura of wealth and power. In 2005, when The New York Times attempted to determine how much money Mr. Trump had, Mr. Weisselberg provided a list of assets that he said would show that Mr. Trump was worth $6 billion.
When the list of assets appeared to add up to only $5 billion, Mr. Weisselberg excused himself.
“I’m going to go to my office and find that other billion,” he said.