Weisselberg surrendered on Thursday to face criminal charges in Manhattan and later pleaded not guilty.
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He was released on his own recognizance.
In January 2017, Weisselberg was named a trustee of the Trump Organization -- along with President Trump's eldest sons, Don Jr. and Eric -- when the president handed over the reins of the company ahead of taking the oath of office.
Weisselberg has been described by sources as knowing more than anyone about the Trump family finances and was granted immunity by federal prosecutors in the Southern District of New York as part of their earlier investigation into former Trump attorney and fixer Michael Cohen.
Now, Weisselberg finds himself in the middle of the New York District Attorney and the New York Attorney General's investigations into the Trump Organization.
He has sat for depositions multiple times in the attorney general's investigation into Trump's finances and allegations of tax fraud, according to his former daughter in law -- who is now cooperating in the investigation.
Jennifer Weisselberg was married for 14 years to Allen's son Barry Weisselberg, who for two decades, managed Trump Organization businesses contracted out by New York City in Central Park, including Wollman Rink and Lasker Rink.
Documents from Jennifer and Barry Weisselberg's divorce show thousands of dollars in payments for cars, rent, tuition, medical bills, and more coming from Allen Weisselberg to his son's family.
The spending and benefits are what attracted scrutiny by prosecutors in both offices. The district attorney has questioned Jennifer Weisselberg about benefits she received during her marriage, including access to Trump-owned rent-free apartments, she previously told CNN.
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More recently, their interest has turned to questions around school tuition payments for her children.
In March of 2021, the DA's office subpoenaed Weisselberg's personal financial records, according to two sources familiar with the matter, as part of the criminal matter.
In May, ABC News reported that Weisselberg faced an ongoing second criminal inquiry by New York Attorney General Letitia James, according to a source familiar with the matter.
Weisselberg's attorney, Mary Mulligan, declined to comment.
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There's nothing illegal about companies giving lavish perks to valued employees, but in many circumstances, those benefits count as compensation subject to income tax.
Trump Organization lawyer Ron Fischetti said any charges against the company based on fringe benefits would be overreach by prosecutors.
"We looked back 100 years of cases and we haven't found one in which an employee has been indicted for fringe benefits - and certainly not a corporation," he said. For it to be a crime, he said, "it would have to be for the benefit of the corporation with the knowledge of the corporation. They don't have the evidence at all."
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The-CNN-Wire & Associated Press contributed to this story
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