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One of Donald J. Trumps longtime lieutenants, Allen H. Weisselberg, was recently released from the notorious Rikers Island jail complex after pleading guilty to a tax fraud scheme. Yet Mr. Weisselbergs legal troubles are far from over.

The Manhattan district attorneys office is now considering a new round of criminal charges against Mr. Weisselberg, 75, and this time he could be charged with perjury, according to people with knowledge of the matter.

The threat of new charges represents the latest effort in a two-year campaign to persuade Mr. Weisselberg to testify against Mr. Trump. And it comes at a crucial time, just weeks after the district attorney, Alvin L. Bragg, unveiled an indictment of the former president.

Mr. Weisselberg has so far refused to turn against his former boss, but the prosecutors recently ramped up the pressure, warning his lawyers that they might bring the perjury charges if their client declined to testify against Mr. Trump, two of the people said.

The potential perjury charges stem fromstatements Mr. Weisselberg made under oath during a 2020 interview with the office of the New York attorney general, Letitia James, who was conducting her own separate civil investigation into Mr. Trump and his family business. It is not clear which part of his testimony raised red flags for prosecutors and Ms. James, or how Mr. Bragg might prove that Mr. Weisselberg intentionally made a false statement.

As a trusted financial gatekeeper to Mr. Trumps family for nearly a half-century, Mr. Weisselberg was privy to behind-the-scenes machinations that could make him a valuable witness on several fronts.

He could help Mr. Bragg in the case unveiled against Mr. Trump last month which stems from a $130,000 hush-money payment to a porn star during the 2016 presidential campaign as well as with a separate investigation into whether Mr. Trump fraudulently inflated his own annual financial statements. Ms. Jamess office is participating in that ongoing investigation.

If Mr. Weisselberg refuses to cooperate, he could face a range of new charges. In addition to pursuing the perjury case, the prosecutors have indicated to his lawyers that they are considering unrelated insurance fraud charges against him.

They also appear to be weighing whether to charge Mr. Weisselberg with inflating the numbers on Mr. Trumps financial statements. The prosecutors recently sought to interview one of Mr. Weisselbergs former Trump Organization colleagues, who might be able to shed light on his involvement in crafting the annual statements, the people said.

There is no sign that Mr. Weisselberg, who recently retired from the Trump Organization with a hefty payout, is close to breaking, or that charges are imminent. But the latest prosecutorial pressure campaign may raise questions about the fairness of threatening a man of advanced age who just got out of jail.

The guy has already been prosecuted and served his time, and hes 75 years old, said Daniel J. Horwitz, a criminal defense lawyer who served in the district attorneys office for nearly a decade. Most defense lawyers are going to scratch their heads and say, Is this fair?

But Stephen Gillers, a legal ethics professor at New York University School of Law, said, There would be nothing improper about charging Mr. Weisselberg a second time with different crimes.

Mr. Weisselbergs lawyer, Seth L. Rosenberg, declined to comment, as did a spokeswoman for Mr. Bragg and a lawyer for Mr. Trump.

Mr. Bragg is not the only prosecutor scrutinizing Mr. Trump. The former president might also face criminal charges in Georgia, where a local prosecutor is examining his effort to undo the 2020 election results, and in Washington, where federal prosecutors are investigating his handling of classified documents, among other matters.

The possibility of new criminal charges from Mr. Bragg marks a return to an earlier focus of the criminal investigation into the former president.

When Mr. Bragg took office in January 2022, prosecutors in his office were already presenting evidence to a grand jury about Mr. Trumps financial statements. His predecessor, Cyrus R. Vance Jr., who did not seek re-election, had authorized the prosecutors to move forward with the case.

But Mr. Bragg soon became skeptical, concerned that they lacked enough evidence to demonstrate Mr. Trumps intent to falsify the statements, a key element of proving the case. Mr. Bragg also lacked confidence in relying on the testimony of Michael D. Cohen, a former fixer for Mr. Trump who was directly involved in the hush-money deal but played a lesser role in Mr. Trumps financial statements.

Enter Mr. Weisselberg, the Trump Organizations former chief financial officer, a role that provided him a front-row seat to the creation of the financial statements.

The district attorneys first pressure campaign against Mr. Weisselberg peaked in the summer of 2021, when Mr. Vance, unable to secure Mr. Weisselbergs assistance, brought criminal charges against him and the Trump Organization in the tax fraud case. Despite refusing to implicate Mr. Trump personally, Mr. Weisselberg ultimately pleaded guilty and testified against the Trump Organization at its trial last year.

The company, which continues to pay for his lawyers, was convicted. And Mr. Weisselberg, as part of a plea deal, served 100 days in the Rikers Island jail.

Now, Mr. Weisselbergs release from jail, rather than representing a reprieve, is expected to deliver him back into the jaws of the same predicament: He can turn on Mr. Trump, or potentially spend the rest of his life behind bars.

Although perjury is a low-level felony, Mr. Weisselberg could still face significant prison time. The judge who has overseen Trump-related cases, Juan Merchan, sentenced Mr. Weisselberg to 100 days in Rikers Island in the tax fraud case and warned him that he typically imposes tougher sentences in white-collar cases.

Even if Mr. Weisselberg were to turn on Mr. Trump, the former presidents lawyers have potential defenses to a case built around the financial statements. Those annual statements, which assigned values to Mr. Trumps hotels, golf clubs and other assets, contained disclaimers noting that the values were unaudited estimates. And in general, assigning values to real estate is a subjective process, not an exact science.

Yet Mr. Vance felt that the financial statements case was strong, even without Mr. Weisselbergs cooperation, leading him to authorize the grand jury presentation before he left office at the end of 2021. The two lead prosecutors on the case, Mark Pomerantz and Carey R. Dunne, continued that presentation in the early days of Mr. Braggs tenure.

When Mr. Bragg halted the presentation in February of last year, it prompted Mr. Pomerantz and Mr. Dunne to resign and set off a media and political uproar that engulfed Mr. Braggs early tenure.

But the investigation continued.

As one group of prosecutors pushed forward with the case centering on a hush-money payment to a porn star the one for which Mr. Trump was recently indicted a separate group continued to investigate Mr. Trumps financial statements.

While the hush case is moving ahead with Mr. Cohen as the prosecutions star witness, Mr. Bragg has been reluctant to charge Mr. Trump for his financial statements without Mr. Weisselberg on board.

And so, while Mr. Weisselberg was behind bars, Mr. Braggs prosecutors told his lawyer that he might face charges in the unrelated insurance fraud inquiry, The Times reported early this year. That inquiry has focused on whether Mr. Weisselberg lied to an insurance company by claiming that the value of the Trump Organizations real estate holdings had been assessed by an independent appraiser, when in fact they had not been.

In recent weeks, the prosecutors broadened their focus to include the potential perjury charge, which would center on Mr. Weisselbergs 2020 interview with Ms. Jamess investigators, the people with knowledge of the matter said. Last year, Ms. James sued Mr. Trump and Mr. Weisselberg for overstating the former presidents net worth by billions of dollars. (Her investigators interviewed Mr. Weisselberg again this month, as Ms. Jamess lawsuit against him and Mr. Trump proceeds.)

In 2020, Ms. Jamess investigators questioned Mr. Weisselberg about some significant errors in Mr. Trumps financial statements. At one point during the interview, court records show, Mr. Weisselberg acknowledged that the Trump Organization had overvalued Mr. Trumps penthouse apartment in Trump Tower by give or take $200 million.

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Trump Ally Could Face Perjury Charge if He Doesn't Cooperate With D.A. - The New York Times