The chief financial officer of the former president’s business is expected to admit to 15 felonies on Thursday and to take the stand at the company’s trial.

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By Ben Protess, William K. Rashbaum and Jonah E. Bromwich

Allen H. Weisselberg, who for decades was one of Donald J. Trump’s most trusted executives, is expected to plead guilty on Thursday to a long-running tax scheme at the former president’s family business — a serious blow to the company that could imperil its chances in an upcoming trial.

The plea deal will allow Mr. Weisselberg, who was facing up to 15 years in prison, to spend as little as 100 days behind bars, according to people with knowledge of the matter. And it does not require Mr. Weisselberg, the Trump Organization’s longtime chief financial officer, to cooperate with the Manhattan district attorney’s office in its broader investigation into Mr. Trump, who has not been accused of wrongdoing.

But Mr. Weisselberg is expected to admit to all 15 felonies he was charged with and will have to testify about his role in a scheme to avoid paying taxes on lavish corporate perks, the people said. That requirement will put the company at a disadvantage and make Mr. Weisselberg a central witness at its trial in October, where it will face many of the same charges.

Mr. Weisselberg is not expected to implicate Mr. Trump or his family when he takes the stand in the October trial, the people said, and on cross-examination, the company’s lawyers could accuse him of pleading guilty only to spare himself a harsher sentence.

But his testimony — an acknowledgment from one of the Trump Organization’s top executives that he committed the crimes listed in the indictment — will undercut any effort by the company’s lawyers to contend that no crime was committed. The indictment placed Mr. Weisselberg at the center of the company’s scheme, and his testimony could enable prosecutors to argue that his admissions go a long way toward proving its broader claims.

The Trump Investigations

The Trump Investigations

Numerous inquiries. Since former President Donald J. Trump left office, he has been facing several civil and criminal investigations into his business dealings and political activities. Here is a look at some notable cases:

The Trump Investigations

Classified documents inquiry. The F.B.I. searched Mr. Trump’s Florida home as part of the Justice Department’s investigation into his handling of classified materials. The inquiry is focused on documents that Mr. Trump had brought with him to Mar-a-Lago, his private club and residence, when he left the White House.

The Trump Investigations

Jan. 6 investigations. In a series of public hearings, the House select committee investigating the Jan. 6 attack laid out a comprehensive narrative of Mr. Trump’s efforts to overturn the 2020 election. This evidence could allow federal prosecutors, who are conducting a parallel criminal investigation, to indict Mr. Trump.

The Trump Investigations

Georgia election interference case. Fani T. Willis, the Atlanta-area district attorney, has been leading a wide-ranging criminal investigation into the efforts of Mr. Trump and his allies to overturn his 2020 election loss in Georgia. This case could pose the most immediate legal peril for the former president and his associates.

The Trump Investigations

New York State civil inquiry. Letitia James, the New York attorney general, has been conducting a civil investigation into Mr. Trump and his family business. The case is focused on whether Mr. Trump’s statements about the value of his assets were part of a pattern of fraud or were simply Trumpian showmanship.

The Trump Investigations

Manhattan criminal case. Alvin L. Bragg, the Manhattan district attorney, has been investigating whether Mr. Trump or his family business intentionally submitted false property values to potential lenders. But the inquiry faded from view after signs emerged suggesting that Mr. Trump was unlikely to be indicted.

The New York Times reported on Monday that Mr. Weisselberg was nearing a deal with prosecutors, and CNN reported Wednesday that he had agreed to testify at the Trump Organization’s trial.

Mr. Weisselberg’s lawyers, Nicholas Gravante Jr. and Mary E. Mulligan, declined to comment, as did a spokeswoman for the Manhattan district attorney’s office.

Mr. Weisselberg, 75, and the Trump Organization were indicted last year by the district attorney’s office and accused of orchestrating a scheme in which some executives were compensated with special off-the-books perks. Mr. Weisselberg, the prosecutors said, avoided paying taxes on $1.76 million of his income over the last 15 years.

The executive, who entered the Trump orbit as a junior bookkeeper for Mr. Trump’s father and climbed the ranks at the Trump Organization in the decades that followed, possessed a peerless knowledge of its business practices, and prosecutors had pressured him to cooperate with their wider investigation into the former president. But the district attorney who indicted him, Cyrus R. Vance Jr., was not able to sway him, and Mr. Vance’s successor, Alvin L. Bragg, has also been unsuccessful.

The deal, though, could represent a victory for Mr. Bragg as his prosecutors prepare for the highest-profile trial of his young tenure.

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