After raising their sons on Long Island, Mr. Weisselberg and his wife moved into a Trump-branded building on Manhattan’s West Side, where they lived rent-free for years. He bought a home in South Florida, not far from Mr. Trump’s Mar-a-Lago resort, and traveled there and back on weekends on Mr. Trump’s jet. His older son, Barry, went to work for the company managing Wollman Rink in Central Park and acted as the D.J. for Mr. Trump’s Christmas parties, where Allen Weisselberg let loose on the dance floor, according to people who attended. In 2004, Mr. Weisselberg appeared in an episode of “The Apprentice,” Mr. Trump’s reality television show.
“They are like Batman and Robin,” said Barry Weisselberg’s ex-wife, Jennifer, who has aided Mr. Vance’s investigation after a contentious divorce. “They’re a team. They’re not best friends. They don’t spend all their time together, but the world became so insular for Allen that he did not know anything else.”
Mr. Weisselberg had become so woven into the fabric of the Trump Organization that when Mr. Trump moved into the White House in 2017, he entrusted Mr. Weisselberg, along with the former president’s adult sons, with running his company. His earnings reflected his importance: Between 2007 and 2017, his total pay averaged nearly $800,000 a year; in 2018, he earned more than $977,000 in salary and deferred compensation, according to tax return data obtained by The New York Times as part of an investigation published last year.
A lawyer for Mr. Weisselberg, Mary E. Mulligan, declined to comment. A lawyer for the Trump Organization could not immediately be reached for comment.
Even before the indictment, Mr. Weisselberg had in recent years been drawn publicly into Mr. Trump’s controversies and scandals, including investigations over the misuse of charitable funds by the Donald J. Trump Foundation and payments to women on Mr. Trump’s behalf to buy their silence about affairs they said they had with Mr. Trump.
Mr. Trump’s former lawyer, Michael D. Cohen, testified in Congress that Mr. Weisselberg had helped orchestrate a cover-up to reimburse him for a $130,000 payment to the adult film actress Stormy Daniels, and that together they had concocted phony valuations of the company’s real estate holdings to suit Mr. Trump’s needs at any given moment.