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.
If the case moves ahead, the district attorney, Cyrus R. Vance Jr., could announce charges against the Trump Organization and the executive, Allen H. Weisselberg, as soon as next week, the people said.
The criminal charges would be the first to emerge from Mr. Vance’s long-running investigation into Mr. Trump and his business dealings, and raise the startling prospect of a former president having to defend the company he founded and has run for decades.
While the prosecutors had been building a case for months against Mr. Weisselberg, the Trump Organization’s chief financial officer, as part of an effort to pressure him to cooperate with the inquiry, it was not previously known that the company also might face charges.
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.
Prosecutors 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.
It would be highly unusual to indict a company just for failing to pay taxes on fringe benefits, said several lawyers who specialize in tax rules. None of them could cite any recent example, noting that many companies provide their employees with perks like company cars.
Still, an indictment of Mr. Trump’s company could deal a significant blow to the former president just as he has flirted with a return to politics.
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 could not immediately be reached 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 byRonald P. Fischetti, a personal lawyer for Mr. Trump. Mr. Fischetti 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.
In the coming days, Mr. Trump’s lawyers might still argue that any charges against the company could take a serious financial toll. Criminal charges, even against private companies like the Trump Organization, can threaten reputations and relationships with banks and business partners.
Companies, like people, can be tried for crimes, and if they are convicted or plead guilty, they can face fines and other penalties.
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,” the former president 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 the former president’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.
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