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Donald Trump’s longtime finance chief is expected to plead guilty as soon as Thursday in a tax evasion case that is the only criminal prosecution to arise from a long-running investigation into the former president’s company, three people familiar with the matter told The Associated Press.

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Allen H. Weisselberg, who for decades was one of Donald J. Trump’s most trusted executives, has reached a deal to plead guilty on Thursday and admit to his role in 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 on related charges.

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 will have to admit to all 15 felonies he was charged with and if called as a witness at the company’s trial 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 Trump Organization at a disadvantage and make Mr. Weisselberg a central witness at the October trial, where the company will face many of the same charges.

Mr. Weisselberg will not implicate Mr. Trump or his family if he takes the stand in that trial, the people said.

And on cross-examination, the Trump Organization’s lawyers could accuse Mr. Weisselberg of pleading guilty only to spare himself a harsher sentence. They might also argue that it would be unfair to hold the Trump Organization accountable for a crime that was not committed by the people who control the company, namely the Trump family.

But Mr. Weisselberg’s testimony — an acknowledgment from one of the Trump Organization’s top executives that he committed the crimes listed in the indictment — would 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 prosecutors also essentially accused him of conspiring with the Trump Organization, which he will have to acknowledge at his plea hearing on Thursday and at the trial if he is called as a witness.

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One of Donald J. Trump’s most trusted executives stood before a judge on Thursday and pleaded guilty to 15 felonies, admitting that he conspired with Mr. Trump’s company to carry out a scheme to avoid paying taxes on lavish perks — even while refusing to implicate the former president himself.

As part of the plea deal with the Manhattan district attorney’s office, the executive, Allen H. Weisselberg, is required to testify at the company’s trial if prosecutors choose to call on him, and to admit his role in conspiring with Mr. Trump’s company to carry out the tax scheme. That testimony could tilt the scales against the company, the Trump Organization, as it prepares for an October trial related to the same accusations.

“Yes, your honor,” Mr. Weisselberg said again and again in response to detailed questions from the judge, Juan Merchan, who asked whether he and the Trump Organization committed the criminal conduct underlying each of the 15 counts.

Under the terms of the plea deal, if Mr. Weisselberg testifies truthfully at the upcoming trial, he will receive a five-month sentence. Mr. Weisselberg, who was facing up to 15 years in prison, must also pay nearly $2 million in taxes, penalties and interest.

The plea deal does not require Mr. Weisselberg to cooperate with the district attorney’s broader criminal investigation of Mr. Trump, and his admissions will not implicate the former president.