One among Donald J. Trump’s longtime lieutenants, Allen H. Weisselberg, was lately launched from the infamous Rikers Island jail advanced after pleading responsible to a tax fraud scheme. But Mr. Weisselberg’s authorized troubles are removed from over.

The Manhattan district legal professional’s workplace is now contemplating a brand new spherical of felony costs towards Mr. Weisselberg, 75, and this time he might be charged with perjury, based on individuals with data of the matter.

The specter of new costs represents the most recent effort in a two-year marketing campaign to influence Mr. Weisselberg to testify towards Mr. Trump. And it comes at a vital time, simply weeks after the district legal professional, Alvin L. Bragg, unveiled an indictment of the previous president.

Mr. Weisselberg has thus far refused to show towards his former boss, however the prosecutors lately ramped up the strain, warning his attorneys that they could carry the perjury costs if their shopper declined to testify towards Mr. Trump, two of the individuals mentioned.

The potential perjury costs stem from statements Mr. Weisselberg made underneath oath throughout a 2020 interview with the workplace of the New York legal professional basic, Letitia James, who was conducting her personal separate civil investigation into Mr. Trump and his household enterprise. It’s not clear which a part of his testimony raised crimson flags for prosecutors and Ms. James, or how Mr. Bragg may show that Mr. Weisselberg deliberately made a false assertion.

As a trusted monetary gatekeeper to Mr. Trump’s household for almost a half-century, Mr. Weisselberg was aware of behind-the-scenes machinations that would make him a helpful witness on a number of fronts.

He may assist Mr. Bragg within the case unveiled towards Mr. Trump final month — which stems from a $130,000 hush-money cost to a porn star in the course of the 2016 presidential marketing campaign — in addition to with a separate investigation into whether or not Mr. Trump fraudulently inflated his personal annual monetary statements. Ms. James’s workplace is taking part in that ongoing investigation.

If Mr. Weisselberg refuses to cooperate, he may face a spread of latest costs. Along with pursuing the perjury case, the prosecutors have indicated to his attorneys that they’re contemplating unrelated insurance coverage fraud costs towards him.

In addition they seem like weighing whether or not to cost Mr. Weisselberg with inflating the numbers on Mr. Trump’s monetary statements. The prosecutors lately sought to interview considered one of Mr. Weisselberg’s former Trump Group colleagues, who may be capable to make clear his involvement in crafting the annual statements, the individuals mentioned.

There is no such thing as a signal that Mr. Weisselberg, who lately retired from the Trump Group with a hefty payout, is near breaking, or that costs are imminent. However the newest prosecutorial strain marketing campaign might elevate questions in regards to the equity of threatening a person of superior age who simply bought out of jail.

“The man has already been prosecuted and served his time, and he’s 75 years previous,” mentioned Daniel J. Horwitz, a felony protection lawyer who served within the district legal professional’s workplace for almost a decade. “Most protection attorneys are going to scratch their heads and say, ‘Is that this truthful?’”

However Stephen Gillers, a authorized ethics professor at New York College College of Regulation, mentioned, “There could be nothing improper about charging Mr. Weisselberg a second time with totally different crimes.”

Mr. Weisselberg’s lawyer, Seth L. Rosenberg, declined to remark, as did a spokeswoman for Mr. Bragg and a lawyer for Mr. Trump.

Mr. Bragg shouldn’t be the one prosecutor scrutinizing Mr. Trump. The previous president may additionally face felony costs in Georgia, the place an area prosecutor is analyzing his effort to undo the 2020 election outcomes, and in Washington, the place federal prosecutors are investigating his dealing with of labeled paperwork, amongst different issues.

The potential of new felony costs from Mr. Bragg marks a return to an earlier focus of the felony investigation into the previous president.

When Mr. Bragg took workplace in January 2022, prosecutors in his workplace have been already presenting proof to a grand jury about Mr. Trump’s monetary statements. His predecessor, Cyrus R. Vance Jr., who didn’t search re-election, had approved the prosecutors to maneuver ahead with the case.

However Mr. Bragg quickly turned skeptical, involved that they lacked sufficient proof to display Mr. Trump’s intent to falsify the statements, a key ingredient of proving the case. Mr. Bragg additionally lacked confidence in counting on the testimony of Michael D. Cohen, a former fixer for Mr. Trump who was instantly concerned within the hush-money deal however performed a lesser function in Mr. Trump’s monetary statements.

Enter Mr. Weisselberg, the Trump Group’s former chief monetary officer, a task that supplied him a front-row seat to the creation of the monetary statements.

The district legal professional’s first strain marketing campaign towards Mr. Weisselberg peaked in the summertime of 2021, when Mr. Vance, unable to safe Mr. Weisselberg’s help, introduced felony costs towards him and the Trump Group within the tax fraud case. Regardless of refusing to implicate Mr. Trump personally, Mr. Weisselberg finally pleaded responsible and testified towards the Trump Group at its trial final yr.

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

Now, Mr. Weisselberg’s launch from jail, slightly than representing a reprieve, is anticipated to ship him again into the jaws of the identical predicament: He can activate Mr. Trump, or doubtlessly spend the remainder of his life behind bars.

Though perjury is a low-level felony, Mr. Weisselberg may nonetheless face vital jail time. The decide who has overseen Trump-related circumstances, Juan Merchan, sentenced Mr. Weisselberg to 100 days in Rikers Island within the tax fraud case and warned him that he usually imposes harder sentences in white-collar circumstances.

Even when Mr. Weisselberg have been to activate Mr. Trump, the previous president’s attorneys have potential defenses to a case constructed across the monetary statements. These annual statements, which assigned values to Mr. Trump’s inns, golf golf equipment and different belongings, contained disclaimers noting that the values have been unaudited estimates. And basically, assigning values to actual property is a subjective course of, not an actual science.

But Mr. Vance felt that the monetary statements case was robust, even with out Mr. Weisselberg’s cooperation, main him to authorize a the grand jury presentation earlier than he left workplace on the finish of 2021. The 2 lead prosecutors on the case, Mark Pomerantz and Carey R. Dunne, continued that presentation within the early days of Mr. Bragg’s tenure.

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

However the investigation continued.

As one group of prosecutors pushed ahead with the case centering on a hush-money cost to a porn star — the one for which Mr. Trump was lately indicted — a separate group continued to analyze Mr. Trump’s monetary statements.

Whereas the hush case is transferring forward with Mr. Cohen because the prosecution’s star witness, Mr. Bragg has been reluctant to cost Mr. Trump for his monetary statements with out Mr. Weisselberg on board.

And so, whereas Mr. Weisselberg was behind bars, Mr. Bragg’s prosecutors instructed his lawyer that he may face costs within the unrelated insurance coverage fraud inquiry, The Occasions reported early this yr. That inquiry has targeted on whether or not Mr. Weisselberg lied to an insurance coverage firm by claiming that the worth of the Trump Group’s actual property holdings had been assessed by an impartial appraiser, when the truth is they’d not been.

In latest weeks, the prosecutors broadened their focus to incorporate the potential perjury cost, which might heart on Mr. Weisselberg’s 2020 interview with Ms. James’s investigators, the individuals with data of the matter mentioned. Final yr, Ms. James sued Mr. Trump and Mr. Weisselberg for overstating the previous president’s internet price by billions of {dollars}. (Her investigators interviewed Mr. Weisselberg once more this month, as Ms. James’s lawsuit towards him and Mr. Trump proceeds.)

In 2020, Ms. James’s investigators questioned Mr. Weisselberg about some vital errors in Mr. Trump’s monetary statements. At one level in the course of the interview, courtroom information present, Mr. Weisselberg acknowledged that the Trump Group had overvalued Mr. Trump’s penthouse condo in Trump Tower by “give or take” $200 million.