Allen H. Weisselberg, one of Donald J. Trump’s most trusted lieutenants, stood before a judge in a Lower Manhattan courtroom on Thursday and admitted that he had conspired with the former president’s company to commit numerous crimes.
Mr. Weisselberg’s guilty plea, which followed more than a year of the Manhattan district attorney’s office pressuring him to cooperate in a broader investigation of Mr. Trump, painted a damning picture of the beleaguered company, which now faces significant financial penalties if it loses its own trial on similar charges.
But for prosecutors who have long sought to indict Mr. Trump, Thursday’s hearing was something of a consolation prize. Mr. Weisselberg refused to turn on Mr. Trump himself, something prosecutors had hoped he would do since they charged him with 15 felonies last July.
Under the plea deal, Mr. Weisselberg must pay nearly $2 million in taxes, penalties and interest after accepting lavish off-the-books perks from Mr. Trump and his company, including leased Mercedes-Benzes, an apartment on Manhattan’s Upper West Side and private school tuition for his grandchildren.
He also must point the finger at his longtime employer, the Trump Organization, at its trial in October. In exchange, Mr. Weisselberg, who was facing years in prison, is likely to receive a five-month jail sentence, and with time credited for good behavior, he might serve as little as 100 days.
The deal emerged after weeks of pitched back-and-forth negotiations. They culminated in a crucial meeting on Monday, Mr. Weisselberg’s 75th birthday, when his lawyers gathered with prosecutors in the judge’s chambers, according to people with knowledge of the matter.
Mr. Weisselberg’s lawyers, Nicholas A. Gravante Jr. and Mary E. Mulligan, pressed for leniency, emphasizing their client’s age, frail health and past service in the National Guard and arguing that the district attorney’s demand for a six-month jail term was excessive.
The judge had previously warned that Mr. Weisselberg’s only chance for probation was cooperating with the broader investigation into Mr. Trump’s business practices. With that off the table, he proposed a compromise: Over the objections of the district attorney’s office, the judge would agree to the five-month sentence.
An examination of how the deal took shape, based on interviews with a half-dozen people knowledgeable about the plea negotiations, underscores Mr. Weisselberg’s bottom line: He would not betray Mr. Trump. For now at least, that unflinching loyalty to a family he has served for nearly a half-century has helped stymie the larger effort to indict the former president.
The interviews also highlight the intense negotiations between Mr. Weisselberg’s lawyers and the district attorney’s office — and the previously unknown role played by the judge, Juan Merchan, to guide the talks — once it became clear that the Trump Organization would refuse to sign a plea deal of its own. Had the company agreed to plead guilty, the judge had offered to impose an even shorter sentence on Mr. Weisselberg, the people said.
In a statement on Thursday, Mr. Gravante said, “In one of the most difficult decisions of his life, Mr. Weisselberg decided to enter a plea of guilty today to put an end to this case and the yearslong legal and personal nightmares it has caused for him and his family.”
He added: “Rather than risk the possibility of 15 years in prison, he has agreed to serve 100 days,” and said, “We are glad to have this behind him.”
Ms. Mulligan declined to comment.
In a statement, the district attorney, Alvin L. Bragg, emphasized how the plea “directly implicates the Trump Organization in a wide range of criminal activity,” adding, “We look forward to proving our case in court against the Trump Organization.”
The district attorney’s investigation into Mr. Trump and his family business began with Mr. Bragg’s predecessor in 2018 and was stalled while Mr. Trump fought a subpoena for his tax returns — a battle that twice reached the U.S. Supreme Court.
But even before the Supreme Court ruled, a new avenue in the investigation opened for prosecutors. Bloomberg News reported that Mr. Weisselberg and his family had received luxury perks, leading prosecutors to focus on him in the hopes of pressuring him to cooperate. When he balked, they indicted Mr. Weisselberg and the company in the tax scheme, bringing charges in July 2021.
The broader investigation into Mr. Trump continued, and in December, the then-district attorney, Cyrus R. Vance Jr., directed his 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 proving that Mr. Trump had intended to commit a crime, a necessary element of any case against the former president. That burden would have been particularly difficult to meet without an inside witness like Mr. Weisselberg.
For that reason, the grand jury presentation about the former president was halted, leading two senior prosecutors to resign and leaving the future of the inquiry — which Mr. Bragg has said continues — uncertain.
Even though he did not secure Mr. Weisselberg’s cooperation, and Mr. Trump appears to be personally unscathed, Mr. Bragg can still declare the plea a victory. Prosecutors now can point to Mr. Weisselberg’s admissions that he conspired with the Trump Organization — weighty evidence against the company — when they face off at trial. And Mr. Weisselberg, an accountant who served a vital role as the company’s financial gatekeeper, will be branded as a felon.
In a statement, the Trump Organization said its two corporate entities under indictment, the Trump Corporation and Trump Payroll Corp., would not plead guilty for “the simple reason that they have done nothing wrong.”
The company also called Mr. Weisselberg “a fine and honorable man who, for the past four years, has been harassed, persecuted and threatened by law enforcement, particularly the Manhattan district attorney, in their never-ending, politically motivated quest to get President Trump.”
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.
In a statement about Mr. Weisselberg’s plea on Thursday, Ms. James, whose office is also participating in the criminal investigation, said, “Let this guilty plea send a loud and clear message: We will crack down on anyone who steals from the public for personal gain because no one is above the law.”
Last week, Ms. James’s office interviewed Mr. Trump under oath, and the former president invoked his Fifth Amendment right against self-incrimination more than 440 times, which a jury could hold against him if Ms. James decides to file a lawsuit against the former president.
Mr. Trump faces a number of other investigations 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.
In the Weisselberg case, a deal proved elusive for nearly a year after his indictment. But in May, one of Mr. Weisselberg’s lawyers, Ms. Mulligan, sent a letter to the prosecutors that helped get the process moving.
Soon after, Mr. Weisselberg added Mr. Gravante to his legal team, and he conveyed a willingness to negotiate behind the scenes.
The first step came in mid-June in the judge’s chambers. Seated around the judge’s conference room table and couch, each side argued the strength of its case, with Mr. Gravante seeking probation for Mr. Weisselberg if he struck a plea deal.
Susan Hoffinger, who is overseeing the case as the head of Mr. Bragg’s investigation division, argued that Mr. Weisselberg would need to serve time in state prison. For the most significant crime he was accused of, the minimum allowable sentence if prison time was imposed was one to three years.
It was then that Justice Merchan, a former prosecutor who has been on the bench for more than a decade, offered a crucial piece of guidance to Mr. Weisselberg’s team: He said he did not think that white-collar criminals deserved to be spared prison time. And if Mr. Weisselberg was convicted, the judge warned that he would order him into custody that same day.
The only way to avoid serving time behind bars, the judge indicated, was if Mr. Weisselberg cooperated and pleaded guilty.
That advice prompted a final attempt to persuade Mr. Weisselberg to provide any details on the way Mr. Trump valued his hotels, golf clubs and other assets.
Mr. Weisselberg insisted that Mr. Trump had done nothing wrong, and that he would rather go to jail than fabricate a story about him. But he did come up with something — that Mr. Trump would occasionally draw a circle around the valuation of an asset on his annual financial statement, adding a question mark beside the number. But Mr. Trump, he said, did not order anyone to inflate the numbers.
When Mr. Weisselberg’s lawyers presented this scant information to the prosecutors in mid-July, they were not impressed.
The negotiations had hit a wall. But Mr. Gravante had a proposal: He offered to try to persuade the Trump Organization lawyers to accept a plea deal, on the condition that Mr. Weisselberg receive a one-month sentence. Justice Merchan, also seeking to break the impasse, agreed to impose a three-month sentence on Mr. Weisselberg if he and the two Trump Organization entities pleaded guilty in the coming weeks.
But Mr. Trump’s company refused to consider pleading guilty to felony charges.
It appeared as if a deal might not materialize until a breakthrough came in recent days. The prosecutors made a new offer: They would be willing to seek only a six-month sentence for Mr. Weisselberg if he pleaded guilty to all 15 felonies, including that he conspired with the company — a move that would tip the scales against the Trump Organization at its October trial. The prosecutors also asked that Mr. Weisselberg’s sentence be imposed after the Trump Organization’s trial, providing them with continuing leverage over him.
When Mr. Weisselberg’s lawyers met with the prosecutors and the judge on Monday, Mr. Gravante pushed for an even shorter sentence, arguing that the Trump Organization’s refusal to plead guilty should not be held against his client. The judge proposed five months, of which Mr. Weisselberg would probably serve 100 days.
The deal was accepted later that day.
While the agreement might hurt the company, it appeared to spare Mr. Trump. And just hours after the deal was made, the Trump Organization threw Mr. Weisselberg a birthday party at Trump Tower.
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