The former president’s family business and its chief financial officer, Allen Weisselberg, are expected to appear in court on Thursday.
A grand jury in Manhattan has indicted Donald J. Trump’s family business, the Trump Organization, and one of its top executives in connection with a tax investigation into fringe benefits handed out at the company, people familiar with the matter said on Wednesday.
The specific charges against the company and its chief financial officer, Allen H. Weisselberg, were not immediately clear. The indictment was expected to be unsealed Thursday afternoon after Mr. Weisselberg and lawyers for the Trump Organization were set to appear in court.
But prosecutors in the Manhattan district attorney’s office have been examining bonuses and luxury perks that Mr. Weisselberg received — including an apartment in Manhattan, leased Mercedes-Benz cars and private school tuition for at least one of his grandchildren — and whether taxes should have been paid on those benefits.
The indictment is a major development in the investigation led by the district attorney, Cyrus R. Vance, Jr., who has been conducting a sweeping inquiry into Mr. Trump and his business dealings along with the New York State attorney general, Letitia James.
It will amplify the pressure that prosecutors have placed on Mr. Weisselberg for months to turn on Mr. Trump and cooperate with their investigation. In nearly a half-century of service to Mr. Trump’s family businesses, Mr. Weisselberg, 73, has survived — and thrived — by anticipating and carrying out his boss’s dictates in a zealous mission to protect the bottom line.
Interviews with 18 current and former associates of Mr. Weisselberg, as well as a review of legal filings, financial records and other documents, paint a portrait of a man whose unflinching devotion to Mr. Trump will now be put to the test.
“Allen is a soldier,” said John Burke, a former Trump executive who worked with Mr. Weisselberg in the early 1990s. “Allen was good at doing what Donald wanted him to do.”
A bookkeeper by training who grew up in Brooklyn, Mr. Weisselberg rose steadily within the Trump Organization to become perhaps the former president’s most trusted business adviser. Over decades, Mr. Weisselberg’s personal and family life became increasingly fused with the company and with Mr. Trump, who is just 14 months older.
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 Times as part of an investigation published last year.
A lawyer for Mr. Weisselberg, Mary E. Mulligan, declined to 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.
Mr. Weisselberg has maintained that keeping a close eye on the organization’s finances and accounting had not given him insight into potential malfeasance at the company. In a 2015 deposition, he made it clear that it was not his job to ensure that the company complied with the law; it was the job of the Trump Organization lawyers.
“I’m the last guy you want to go to for legal advice,” Mr. Weisselberg said in the testimony, for a class-action lawsuit accusing Trump University of fraudulent marketing. Mr. Trump eventually settled litigation over the defunct for-profit venture for $25 million.
For most of his professional career, Mr. Weisselberg operated behind the scenes, looking the part of the prototypical accountant: a man of middling height in a pinstriped or dark suit, with glasses, a mustache and a raspy voice. He seemed to be always at work, from early in the morning to late at night, and almost never took vacations, by his own account and those of others. Employees entering Mr. Trump’s office often found Mr. Weisselberg already inside, seated in the chair to the right facing the boss’s desk.
Mr. Weisselberg studied finance and accounting at Pace College and, after a brief stint as a teacher and at small financial firms, began working in 1973 for Mr. Trump’s father, Fred, then a prominent developer in Brooklyn and Queens. A few years later, he took on projects at night and on weekends for Donald Trump, who was establishing his own presence as a developer in Manhattan. Mr. Weisselberg joined Donald Trump full-time in 1986, he testified in the 2015 deposition.
In the early years, he held the title of controller, and eventually, Mr. Trump elevated him to the loftier post of chief financial officer. Mr. Weisselberg had a wide portfolio: He established an accounting department at the Trump Organization, worked on the financing and management of properties and helped with the company’s and Mr. Trump’s personal tax returns, he has said.
Among the tasks Mr. Weisselberg attacked with fervor, former employees recalled, was ensuring that, per Mr. Trump’s direction, no dime left the company’s coffers unless absolutely necessary.
“He and Trump were like Frick and Frack when it came to stiffing vendors,” Mr. Cohen — who at times took on that same role for Mr. Trump — wrote in a book published last year. Mr. Burke, who served as chief financial officer for Mr. Trump’s casino business, said any Trump employee who dealt with vendors knew to “squeeze every penny” out of people, and that Mr. Weisselberg excelled at minimizing and delaying payment.
In the office, different sides of Mr. Weisselberg’s personality emerged. With Mr. Trump and his children, or anyone on his level or higher, he appeared mild-mannered, even solicitous. When he received good news about some financial matter, he would hurry down the hall to inform Mr. Trump, said Angel Lopez, who worked in the Trump Organization’s accounting department between 2007 and 2014.
“He always wanted to impress Donald Trump,” Mr. Lopez said.
With those who worked for him, Mr. Weisselberg could be collegial in one moment and volatile in the next. He would often accompany a few of the men in the accounting department to buy lunch at the same deli on West 56th Street. But if he perceived that someone made a mistake, he would yell so loudly he could be heard from behind his closed door, Mr. Lopez said.
Mr. Weisselberg acknowledged he could be a “micromanaging” boss.
“People do know it’s important to involve me when it comes to financial matters,” he said in the 2015 deposition. “Because later on, if things don’t prove out to be where they should be, they’ll have to deal with me on answering the question as to why.”
Mr. Weisselberg did not flinch when it came to denying raises or cutting bonuses to achieve Mr. Trump’s ends.
Rana Williams, who managed Mr. Trump’s sales and leasing division, accused his company in a 2013 lawsuit of illegally withholding $735,000 from her after the company reduced agents’ commissions to 25 percent from 35 percent as the financial crisis unfolded in late 2007.
After her plea to keep the commissions higher was rejected, she sent a letter explaining why she would continue to bill Mr. Trump at the 35 percent rate. Mr. Weisselberg scrawled a note to an assistant at the bottom: “Change Rana’s payment to 25 percent,” he wrote. “Ignore her letter.”
Mr. Weisselberg said in a deposition for that lawsuit that the company had every right to cut the commissions and that Ms. Williams had been free to leave. She testified that she held Mr. Trump responsible. “Allen was delivering a message,” she said.
The lawsuit settled on undisclosed terms. Reached by phone this week, Ms. Williams declined to comment except to say that she is “a fan” of Mr. Weisselberg. She continues to market multimillion-dollar apartments at Trump Tower in Manhattan, according to the listing page at her current brokerage.
But more recently, Mr. Weisselberg’s actions on behalf of Mr. Trump have made him vulnerable. When federal prosecutors charged Mr. Cohen in 2018 with various crimes, including campaign finance violations for the payment to Ms. Daniels, they described Mr. Weisselberg as “Executive-1,” according to people familiar with the matter who requested anonymity because they were not authorized to discuss the case. Mr. Weisselberg instructed a subordinate to classify the reimbursement to Mr. Cohen as legal fees, even though no legal services were performed, prosecutors wrote.
In his congressional testimony, Mr. Cohen pinned blame for masking the repayment scheme on Mr. Weisselberg.
Ultimately, the federal prosecutors scrutinized whether Mr. Weisselberg had committed perjury when he told a grand jury that he was unaware that the payment to Mr. Cohen involved reimbursement for the hush money, according to people with knowledge of the matter. (A person familiar with Mr. Weisselberg’s account has said he disputed Mr. Cohen’s assertions that Mr. Trump was involved in the payment to Ms. Daniels or the reimbursement.)
By July 2019, the investigation appeared to be over, and the federal prosecutors never accused Mr. Weisselberg of any wrongdoing.
Since then, Mr. Vance’s investigation has picked up speed, and Mr. Weisselberg has remained in the public eye.
The ordeal of living in the cross hairs of a criminal investigation, and seeing his name in a drumbeat of recent media coverage, has not discouraged Mr. Weisselberg from working. Over the last few months, he has continued to show up at Trump Tower, at times coming face-to-face with Mr. Trump.
But now, the Trump Organization’s lawyers have taken steps to avoid the appearance of any impropriety. In the past, many of Mr. Trump and Mr. Weisselberg’s conversations were private and behind closed doors. Now, they are under instructions to meet in the presence of a witness.
William K. Rashbaum, Russ Buettner and Susanne Craig contributed reporting. Susan Beachy contributed research.
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