Allen Weisselberg, a Top Trump Executive, to Plead Guilty in Tax Scheme

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

As part of the plea deal, the executive, Allen H. Weisselberg, will be 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.

Under the terms of the plea deal, Mr. Weisselberg is expected to receive a five-month jail term, and with time credited for good behavior, he is likely to serve about 100 days.

The plea deal does not require Mr. Weisselberg to cooperate with a broader investigation into Mr. Trump, and his admissions will not implicate the former president. His decision to accept jail time underscored the extent of his loyalty to a family he has served for nearly a half-century.

Mr. Weisselberg was indicted alongside Mr. Trump’s family business last year and accused of participating in a scheme in which some employees were compensated with special off-the-books perks. Mr. Weisselberg, prosecutors from the Manhattan district attorney’s office said, avoided paying taxes on $1.76 million of his income over the last 15 years.

The Trump Investigations

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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.

In refusing to cooperate against Mr. Trump, Mr. Weisselberg fended off intense pressure from prosecutors fighting for his testimony. They saw Mr. Weisselberg as the ideal cooperator in their wider investigation focused on the former president and his business practices: He entered the Trump orbit in the early 1970s as a junior bookkeeper for Mr. Trump’s father and climbed the ranks at the Trump Organization in the decades that followed, developing an encyclopedic knowledge of its finances.

Despite not securing Mr. Weisselberg’s cooperation, the Manhattan district attorney, Alvin L. Bragg may gain a victory from the deal. His prosecutors now have a potential star witness as they prepare for trial against the Trump Organization. And Mr. Weisselberg, an accountant who served a vital role as the company’s financial gatekeeper, will be branded as a felon.

His plea comes as a number of other investigations swirl around the former president related to his efforts to overturn the 2020 election and his handling of sensitive documents after he left the White House. Last week, F.B.I. agents searched his Florida home, a stunning move that underscores the extent of Mr. Trump’s legal jeopardy.

Mr. Trump is also the subject of a civil investigation being conducted by the New York State attorney general, Letitia James. That inquiry is focused on whether Mr. Trump fraudulently inflated the value of his hotels, golf clubs and other assets to obtain loans.

Last week, Ms. James interviewed Mr. Trump under oath, and the former president invoked his Fifth Amendment right against self-incrimination more than 440 times. Ms. James, whose office also worked on the criminal case against Mr. Weisselberg, will now have to decide whether to file a lawsuit against the former president.

The charges to which Mr. Weisselberg will plead Thursday stemmed from a yearslong criminal investigation conducted by the Manhattan district attorney’s office. Like Ms. James’s civil inquiry, the criminal investigation came to focus on Mr. Trump’s financial statements and the way he represented the value of his assets.

The investigation, which started in 2018, proceeded in fits and starts and was stalled when Mr. Trump fought against the release of his tax returns and other records to the office in a battle that twice reached the U.S. Supreme Court.

While prosecutors were waiting for a final ruling from the court, they began to scrutinize Mr. Weisselberg and the perks he had received from the Trump Organization, including leased Mercedes-Benzes, an apartment on Manhattan’s Upper West Side and private school tuition for his grandchildren.

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Key developments in the inquiries into the former president and his allies.

  • A Plea Deal: Allen H. Weisselberg, a longtime Trump executive who was indicted along with the Trump Organization on tax charges by the ​​Manhattan district attorney’s office, is expected to plead guilty and testify at the company’s upcoming trial.
  • Giuliani in Georgia: Rudolph W. Giuliani, who has been told that he is a target in a criminal investigation into election interference in the state, appeared before an Atlanta grand jury.
  • Trump Lawyers Interviewed: Pat A. Cipollone and Patrick F. Philbin, the White House counsel and his deputy under former President Donald J. Trump, were interviewed by the F.B.I. in the investigation into Mr. Trump’s handling of classified material.
  • Invoking the Fifth Amendment: Sitting for a deposition in the New York attorney general’s civil inquiry into his business practices, Mr. Trump repeatedly invoked his constitutional right against self incrimination.

After they obtained the tax returns, they continued to scrutinize Mr. Weisselberg, hoping to pressure him to cooperate. When they did not receive that cooperation, they indicted Mr. Weisselberg and the company in the tax scheme.

The broader investigation continued, and in December, Mr. Bragg’s predecessor, Cyrus R. Vance Jr., asked prosecutors to begin presenting evidence about Mr. Trump to a grand jury. But Mr. Bragg, who was sworn in on Jan. 1, grew concerned about prosecutors’ ability to show that Mr. Trump had intended to commit a crime, and the presentation was halted.

In February, the two prosecutors who had led the investigation resigned from the office, leaving its future unclear. Mr. Bragg has said that it has continued, but there has been no public indication of its direction in recent months.

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