Earlier this month, on a warm fall Saturday evening, more than 200 people, mostly uptown teenagers, milled about the clubhouse overlooking the East River from an event space on 192 acres built over a landfill in the Bronx. There was a sushi station set up for adults, a room decorated in rose golds and silvers and metallics, lounge furniture that had been brought in for the evening, and a DJ playing as everyone in the room celebrated the bat mitzvah of Allen Weisselberg’s granddaughter. Weisselberg, the longtime Trump family accountant and Trump Organization CFO, had gotten the room from the Trumps for free, though no one would have known it. No Trump family members were in attendance at the property, which reported a loss of $122,000 last year. When the invitation went out, neither Donald Trump’s surname nor the club’s official name—Trump Golf Links at Ferry Point—was printed. It read simply that the party was at the Golf Link at Ferry Point.

The fact that the president of the United States was partly underwriting the event by supplying the room, but was nowhere mentioned, speaks to the complicated position in which Weisselberg now finds himself. For four and a half decades, Weisselberg has dedicated his life to ensuring that the Trumps understand that every penny of their money is accounted for under his watchful eye. As Trump’s attorneys and henchmen in all corners of his life, past and present, fall under various degrees of scrutiny or investigation, and have their fealty tested in a high-stakes game of CYA, Weisselberg has been one of the only people whose intentions and loyalty Trump has not yet had to question. As the president told Bloomberg last year, when asked if he thought Weisselberg had turned on him, “100% he didn’t.”

That assurance has been built over decades. Weisselberg began doing books for Trump’s father, Fred, in 1973, and has remained involved with the Trump Organization, handling everything from real estate deals to Trump University. (In a deposition for the lawsuit filed by students who said they’d been defrauded by the educational property, Weisselberg answered a question about his role by saying, “Am I his eyes and ears? From an economic standpoint.”) He was also involved in the hush money payment to Stormy Daniels—a scheme that came under investigation from the Southern District of New York last year, and which ended in Trump’s former attorney Michael Cohen going to prison for campaign-finance violations. Under oath, in front of both the judge in the case and Congress last year, Cohen identified Trump and Weisselberg as having been involved in discussions about him paying Daniels out of an LLC he set up, with the Trump Organization later reimbursing him for the payment.

In the SDNY investigation, Weisselberg was granted limited immunity to testify before a grand jury, though it is unclear if he actually participated in the investigation. Earlier this year, Weisselberg was heard at an uptown function discussing the fact that he was granted “full immunity” in the case, and describing the investigation as “only having to do with Michael.” The SDNY declined to indict anyone besides Cohen in the case, though Weisselberg and Donald Trump Jr. signed at least one reimbursement check to Cohen, and Cohen testified about a meeting with Weisselberg in which Trump said “to go back to Weisselberg’s office and figure this [the $130,000 payment to Daniels] all out.”

The Justice Department has abided by a policy that a sitting president cannot be indicted. Earlier this year, however, the New York state attorney general’s office opened an investigation into whether the Trump Organization and associated individuals violated a state law by potentially falsifying business records to count the reimbursements made to Cohen as retainer fees. The A.G.’s office has paid a couple of visits to Cohen at the federal prison where he started serving his sentence in May. According to several people familiar with the investigation, they have been asking about Weisselberg’s role in the Trump Organization, as well as the roles of the Trump children. (Weisselberg and the Trump Organization did not respond to requests seeking comment.)