Allen H. Weisselberg, former President Donald J. Trump’s longtime financial gatekeeper, pleaded guilty to felony perjury charges in a Manhattan courtroom on Monday, the latest twist in a tortured legal odyssey.
Yet Mr. Weisselberg, who for years has remained steadfastly loyal to Mr. Trump in the face of intense prosecutorial pressure, did not implicate his former boss. That unbroken streak of loyalty has frustrated prosecutors and now, at the age of 76, will cost Mr. Weisselberg his freedom a second time.
The plea agreement with the Manhattan district attorney, Alvin L. Bragg, comes weeks before the former president will stand trial on unrelated criminal charges. That case, also brought by Mr. Bragg, stems from a hush-money payment made on Mr. Trump’s behalf to a porn star during the 2016 presidential campaign.
Mr. Weisselberg, who was led into the courtroom in handcuffs wearing a blue surgical mask and a dark suit, conceded that in recent years he had lied under oath to the New York attorney general’s office when it was investigating Mr. Trump for fraud. The attorney general, Letitia James, sued Mr. Trump in 2022, accusing him of wildly inflating his net worth to obtain favorable loans and other benefits.
That civil case recently ended with a judge imposing a huge financial penalty on the former president — more than $450 million with interest. Mr. Weisselberg, who was also a defendant in the case, was penalized $1 million plus interest and permanently banned from serving in a financial position at any New York company.
Although Mr. Weisselberg neither committed violence nor orchestrated an elaborate scheme, Mr. Bragg’s prosecutors argued that perjury undermines the broader ends of justice and cannot be ignored.
Gary Fishman, one of the prosecutors, on Monday underscored the harm caused by perjury, which he said “tears at the very fabric of our justice system.”
Prosecutors sought a five-month sentence for Mr. Weisselberg, acknowledging his age in coming to their recommendation; his sentencing before the judge in the case, Laurie Peterson, is scheduled for April 10.
Mr. Weisselberg, who pleaded guilty to two counts of perjury related to his testimony in a July 2020 deposition with Ms. James’s office, stood placidly on Monday as he answered the judge’s questions about his plea, often with one-word responses.
He also admitted to lying at the civil fraud trial, but did not plead guilty to that, a move that will spare him a steeper sentence.
“Allen Weisselberg looks forward to putting this situation behind him,” one of Mr. Weisselberg’s lawyers, Seth L. Rosenberg, said in a statement released by his firm.
Mr. Weisselberg has often been caught in the middle of Mr. Trump’s legal travails, facing pressure from several law enforcement agencies in both civil and criminal cases. As the long-serving chief financial officer for Mr. Trump’s family business — his trusted moneyman — Mr. Weisselberg was considered a linchpin in efforts to implicate him.
Mr. Weisselberg has been rewarded for his loyalty to the family he served for nearly a half century: When he left the company, the Trump Organization, last year, he was awarded a $2 million severance package that required him not to cooperate with any law enforcement investigation unless legally required.
He also paid a price. In 2022, he pleaded guilty in a tax fraud case. Although he did not implicate Mr. Trump, he agreed to testify against the Trump Organization at its trial on the same charges.
In that case, the company was convicted, and Mr. Weisselberg received a five-month sentence. With good behavior, he served nearly 100 days behind bars at the notorious Rikers Island jail complex.
Mr. Weisselberg now faces another stint at Rikers. He did not respond to questions from reporters on Monday as he left the courthouse at 100 Centre Street after entering his plea. He piled into the back seat of a black Cadillac Escalade parked outside, surrounded by a phalanx of news photographers and television camera crews.
Mr. Weisselberg’s deal comes at an inopportune time for Mr. Trump, just weeks before he is expected to go to trial on a raft of felony charges accusing him of falsifying business records related to the hush-money deal with the porn star, Stormy Daniels. The trial, the first criminal prosecution of a former president, is scheduled to begin with jury selection on March 25.
Mr. Bragg has accused Mr. Trump of orchestrating a cover-up of a potential sex scandal involving Ms. Daniels that could have influenced the outcome of the 2016 election.
Monday’s guilty plea could strengthen Mr. Bragg’s hand heading into the trial, deterring other witnesses in Mr. Trump’s circle from lying on the stand. The perjury charges could also discredit Mr. Weisselberg, who has disputed details of the prosecution’s evidence in the case.
For his part, Mr. Trump has lashed out at Mr. Bragg, a Democrat, accusing him of persecuting Mr. Weisselberg. And Mr. Trump’s allies have lamented that Mr. Weisselberg will have to again serve time behind bars well into his 70s, and have disputed that he lied in the civil fraud case brought by Ms. James, another Democrat.
Ms. James filed her lawsuit in 2022, and it led to a trial late last year. In February, the judge presiding over the nonjury case sided with the attorney general, concluding that Mr. Trump had manipulated the value of his properties. The judge, Arthur F. Engoron, imposed a sweeping array of punishments, including the more than $450 million judgment.
A focus of the case — and Mr. Weisselberg’s testimony — was Mr. Trump’s triplex apartment in Trump Tower, which is 10,996 square feet, but had been listed for years on his annual financial statements as measuring 30,000 square feet.
Before Ms. James filed the lawsuit, in a 2020 deposition under oath, Mr. Weisselberg played down his involvement in valuing the triplex. He did the same in a second deposition last year, after the suit was filed. And on the witness stand at the trial, Mr. Weisselberg claimed that he “never focused” on the unit.
Yet soon after, Forbes magazine, which compiles a list of America’s richest people, published an article citing emails and notes showing that Mr. Weisselberg “played a key role in trying to convince Forbes over the course of several years” of the apartment’s value.
On Monday, Mr. Weisselberg admitted to lying about when he learned the actual size of the triplex and whether he had ever been present when Mr. Trump had inflated its square footage.
Justice Engoron concluded that Mr. Weisselberg was not a credible witness, in part because of his severance agreement, which is paid in installments over time, as if to keep Mr. Weisselberg in thrall to the Trump family.
“His testimony in this trial was intentionally evasive, with large gaps of ‘I don’t remember,’” the judge wrote in his decision last month, adding that the severance agreement “renders his testimony highly unreliable.”
“The Trump Organization keeps Weisselberg on a short leash,” the justice wrote. “And it shows.”
Wesley Parnell contributed reporting.
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