If finalized, a plea deal for the executive, Allen H. Weisselberg, would bring prosecutors no closer to indicting the former president but would still brand one of his most trusted lieutenants as a criminal. On Monday, Mr. Weisselberg’s lawyers and prosecutors met with the judge overseeing the case, according to a court database. The judge set a hearing for Thursday, a possible sign that a deal has been reached and then a plea could be filed. While Mr. Weisselberg, 75, faces financial penalties as well as up to 15 years in prison if convicted by a jury, a deal would avoid a high-profile trial and likely spare him a lengthy sentence. Two people with knowledge of the matter said Mr. Weisselberg is expected to be sentenced to five months in prison. With time credited for good behavior, he is likely to serve about 100 days. Other terms of Mr. Weisselberg’s deal were not clear, including whether he had made additional concessions to prosecutors to receive it. His attorney, Nicholas A. Gravante Jr., confirmed he was in negotiations but declined to discuss details. Another lawyer for Mr. Weisselberg, Mary E. Mulligan, declined to comment, as did a spokesman for the Manhattan district attorney, Alvin L. Bragg. Over the past few years, the district attorney’s office has been investigating 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, has grown into one of the biggest legal threats Mr. Trump has faced. The district attorney’s criminal investigation continued after Mr. Weisselberg was charged last summer with participating in a 15-year scheme to receive off-the-books benefits at Mr. Trump’s company, the Trump Organization, which was also indicted in the case. The company will not join Mr. Weisselberg in pleading guilty Thursday, two people with knowledge of the matter said. And Mr. Weiselberg, while admitting his own guilt, is not expected to implicate anyone in the Trump family. Prosecutors had long hoped they could get Mr. Weiselberg to testify against Trump, given his decades of working for the Trump family and his vast knowledge of the company and its business practices. But Mr. Weisselberg refused to meet with them, even as his lawyers negotiated a possible deal, the people familiar with the matter said. Mr. Trump and his team have long argued that Mr. Weiselberg would have to lie to implicate Mr. Trump. But his decision to plead guilty — and accept prison time — underscores the extent of his loyalty to a family that has employed him for nearly half a century.

The Trump investigations

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The Trump investigations

Numerous surveys. Ever since Donald J. Trump left office, the former president is facing several different civil and criminal investigations across the country into his business dealings and political activities. Here’s a look at some notable cases:

The Trump investigations

January 6 investigations. In a series of public hearings, the House select committee investigating the Jan. 6 attack presented a powerful account of Mr. Trump’s efforts to sway the 2020 election. That evidence could allow federal prosecutors, who are conducting a parallel criminal investigation, to indict Mr. Trump.

The Trump investigations

Election interference case in Georgia. Mr. Trump himself is under scrutiny in Georgia, where the Fulton County District Attorney is investigating whether he and others criminally interfered in the state’s 2020 election. This case could represent the most immediate legal danger for the former president and his associates. A plea deal for Mr. Weiselberg could leave Mr. Trump’s company on trial only in the tax case. A deal is also likely to draw renewed attention to the status of the attorney general’s criminal investigation into Mr. Trump and his company’s business practices, an investigation that lost momentum early this year and has largely disappeared since common view. Mr. Bragg, a Democrat like Vance, said the investigation was ongoing. But its direction and future are unclear. Mr Trump, who has called the investigation a partisan witch hunt, has not himself been accused of wrongdoing. The plea negotiations with Mr. Weisselberg came to light after New York State Judge Juan Merchan last week refused to dismiss the criminal case against the Trump Organization and Mr. Weisselberg.

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The judge’s ruling marked the latest legal blow for Mr. Trump, whose Florida home was recently searched by the FBI in connection with an unrelated investigation. In another embarrassing episode for a former president who mocked others for refusing 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. Attorney General Letitia James, a Democrat, is conducting a political investigation into some of the same conduct being investigated by the district attorney. And some of her office’s attorneys were involved in the district attorney’s criminal investigation last year. The Manhattan district attorney’s investigation was sidelined early last year, shortly after Mr. Vance won a Supreme Court victory that ended a battle to obtain Mr. Trump’s tax returns and other business records. Armed with those records, prosecutors began focusing on perks Mr. Weisselberg had received from the company, including several leased Mercedes-Benzes, a rent-free apartment and private schools for his grandchildren. Mr. Weisselberg, prosecutors said when they charged him last July, failed to pay taxes on $1.7 million in benefits and other income. Before he was charged, prosecutors put significant pressure on Mr. Weiselberg to cooperate in their investigation of Mr. Trump because of his in-depth understanding of the inner workings of the Trump Organization. But Mr. Weisselberg, who was chief financial officer at the time, did not make a deal and was charged. The Trump Organization has since stripped him of his title, though he continues to work for the company and appeared ready to stand trial. But Mr. Gravante, who also represented two other Trump Organization employees who were not charged in the case, joined Mr. Weisselberg’s defense team in June and signaled he was open to reaching a deal. The Trump Organization, where Mr. Weisselberg spent his career rising through the ranks from junior accountant to chief financial officer, was also charged in the indictment, which described a scheme coordinated by senior executives at the company to understate their income by accepting benefits that were not listed on the tax documents. Even without Mr. Weiselberg’s cooperation, 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, setting the stage for a possible indictment against the former president. But Mr. Vance had decided not to run for re-election, and after weeks of meetings on the case, Mr. Bragg raised concerns about the challenge of showing that Mr. Trump intended to break the law, a requirement for proof of the category according to visa. The two senior prosecutors leading the investigation, Carey R. Dunne and Mark F. Pomerantz, resigned shortly afterward. In his resignation letter, obtained by The New York Times, Mr. Pomerantz said that Mr. Trump was guilty of “numerous criminal violations” and that it was a “serious miscarriage of justice” not to be charged and held accountable. .