Allen H. Weisselberg, the former Trump Organization finance chief, has already spent time at the Rikers Island jail complex. A perjury plea could send him back.
Allen H. Weisselberg, a longtime lieutenant to former President Donald J. Trump, has reached an agreement with Manhattan prosecutors to plead guilty to perjury charges on Monday, according to people with knowledge of the matter.
Yet Mr. Weisselberg, who for years has remained steadfastly loyal to Mr. Trump in the face of intense prosecutorial pressure, is not expected to implicate his former boss. That unbroken streak of loyalty has frustrated prosecutors and already once cost him his freedom.
Mr. Weisselberg, 76, is now expected to concede that he lied to investigators from the New York attorney general’s office when they were investigating Mr. Trump for fraud. The attorney general, Letitia James, had accused Mr. Trump 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, was penalized $1 million plus interest and permanently banned from serving in a financial position of any New York company.
A lawyer for Mr. Weisselberg, Seth L. Rosenberg, could not immediately be reached for comment.
Mr. Weisselberg’s 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.
The perjury plea marks the latest twist in a tortured legal odyssey for Mr. Weisselberg, who squared off against several law enforcement agencies in both civil and criminal trials. As the long-serving chief financial officer for the Trump family business — the former president’s trusted moneyman — Mr. Weisselberg was considered a linchpin in efforts to implicate Mr. Trump.
