Allen H. Weisselberg, a longtime top executive at Donald J. Trump’s family business who was indicted on tax charges last summer, is nearing a plea deal with prosecutors from the Manhattan district attorney’s office but would not cooperate with a broader investigation into Mr. Trump, according to two people with knowledge of the matter.
His plea deal, if finalized, would bring prosecutors no closer to indicting the former president but would nonetheless brand one of his most trusted lieutenants a felon.
On Monday, Mr. Weisselberg’s lawyers and prosecutors met with the judge overseeing the case, according to a court database. The judge scheduled a hearing for Thursday in Mr. Weisselberg’s case, a possible indication that a deal has been reached and a plea could be entered then.
While Mr. Weisselberg, 75, is facing financial penalties as well as years in prison if convicted at trial, a plea deal would scrap a high-profile trial and most likely would spare him from a lengthy sentence. One person with knowledge of the matter said that Mr. Weisselberg was expected to receive a five-month prison sentence, an unexpectedly favorable outcome for him.
The other terms of Mr. Weisselberg’s deal were not clear, and his lawyer, Nicholas A. Gravante Jr., confirmed that he was in discussions with prosecutors, but declined to discuss the specifics. Another lawyer for Mr. Weisselberg, Mary E. Mulligan, declined to comment, as did a spokeswoman for the Manhattan district attorney, Alvin L. Bragg.
The district attorney’s long-running criminal investigation continued after Mr. Weisselberg was charged with taking part in a 15-year scheme to receive off-the-books perks at Mr. Trump’s company, the Trump Organization, which was also indicted in the case.
Prosecutors have long hoped that they could persuade Mr. Weisselberg to testify against Mr. Trump, given his decades in the employ of the Trump family and his vast knowledge of the company and its business practices. But Mr. Weisselberg has refused to meet with them even as his lawyers negotiated a potential deal, the people with knowledge of the matter said.
A plea agreement for Mr. Weisselberg could leave Mr. Trump’s company to face trial in the tax case alone. A deal would also be likely to draw renewed attention to the status of the district attorney’s criminal investigation of Mr. Trump and his company’s business practices, which lost momentum early this year and has largely disappeared from public view.
Mr. Bragg, a Democrat, has said the investigation is continuing. But its direction and future are unclear. Mr. Trump, who has called the investigation a partisan witch hunt, has himself not been accused of wrongdoing.
The plea negotiations with Mr. Weisselberg came to light after a New York State judge, Juan Merchan, last week declined to toss out the criminal case against the Trump Organization and Mr. Weisselberg.
The judge’s decision marked the latest legal blow to Mr. Trump, whose Florida home was recently searched by the F.B.I. in connection with an unrelated investigation. In another embarrassing episode for a former president who has mocked others who have declined to answer questions under oath, he invoked his Fifth Amendment right against self-incrimination in an interview with the New York state attorney general last week.
The attorney general, Letitia James, a Democrat, is conducting a civil inquiry into some of the same conduct that the district attorney is investigating.
In fits and starts over the last few years, the district attorney’s office has been examining whether Mr. Trump and his company fraudulently inflated the value of his real estate to obtain loans and benefits. The investigation, initially led by Cyrus R. Vance Jr., the district attorney at the time, also a Democrat, evolved into one of the greatest legal threats Mr. Trump faced.
The investigation took a detour early last year shortly after Mr. Vance won a victory at the Supreme Court that ended a battle to obtain Mr. Trump’s tax returns and other business records.
Armed with those records, the prosecutors began to focus on perks Mr. Weisselberg had received from the company, including several leased Mercedes-Benzes, a rent-free apartment and private school tuition for his grandchildren. Mr. Weisselberg, prosecutors said when they charged him last July, failed to pay taxes on $1.7 million in perks and other income.
Before he was charged, prosecutors applied significant pressure on Mr. Weisselberg to cooperate with their investigation into Mr. Trump because of his in-depth understanding of the Trump Organization’s inner workings.
But Mr. Weisselberg, who was chief financial officer at the time, did not strike a deal, leading to his indictment. Since then, the Trump Organization has stripped him of his title, though he continues to work at the company.
The Trump Organization, where Mr. Weisselberg spent his career climbing the ranks from junior accountant to chief financial officer, was also charged in the indictment, which outlined a scheme coordinated by senior executives at the Trump Organization to underreport their income by accepting benefits that were not listed on tax documents.
Even without Mr. Weisselberg’s cooperation, the prosecutors continued to build a case against Mr. Trump, focusing on whether he falsely inflated the value of his hotels, golf clubs and other assets.
Late last year, Mr. Vance directed prosecutors to begin presenting evidence about Mr. Trump to a grand jury, laying the groundwork for a potential indictment of the former president.
But Mr. Vance had decided not to run for re-election, and after weeks of meetings about the case, Mr. Bragg developed concerns about the challenge of showing that Mr. Trump intended to break the law, a requirement for proving the charge under consideration.
The two senior prosecutors who had been leading the investigation, Carey R. Dunne and Mark F. Pomerantz, resigned shortly afterward. In his resignation letter, which was obtained by The New York Times, Mr. Pomerantz said that Mr. Trump had been guilty of “numerous felony violations” and that it was “a grave failure of justice” not to bring charges and hold him accountable.