At the Heart of the Trump Organization Accusations: The Lifestyle of CFO Allen Weisselberg

Over four decades, Allen Weisselberg rose from junior accountant to Donald Trump’s father, Fred, to become the top executive of the Trump Organization outside the Trump family.

Now, a New York jury has indicted Mr. Weisselberg and the Trump Organization for tax crimes following investigations by the Manhattan district attorney’s office and the New York attorney general’s office into whether Mr. Weisselberg received amenities such as Manhattan apartments, Mercedes sedans and other expensive items from the Trump Organization for which he or his company did not pay taxes. Mr Weisselberg was charged with grand theft and tax fraud, among other things, with prosecutors saying he illegally evaded paying taxes on $1.7 million in income.

The allegations are the first to stem from a three-year investigation into former President Trump and his company. Mr Weisselberg turned himself in on Thursday morning and pleaded not guilty.

The investigation into whether the Trump Organization and its employees illegally evaded taxes on benefits is part of a larger investigation by Manhattan prosecutors examining potential bank, insurance and tax fraud, The Wall Street Journal has reported. Prosecutors have requested cooperation from Mr. Weisselberg, a confidant of the former president whose complex knowledge of the Trump Organization’s finances can provide a roadmap of the company’s business practices, the Journal reports.

Lawyer Mr. Weisselberg said he intended to fight the charges in court.

Receiving benefits—such as a free apartment, subsidized rent, or car rental—from an employer, and not paying taxes on those benefits, can be a crime, although defense attorneys say prosecutors rarely bring cases about such benefits alone.

Trump called the investigation a “witch hunt” and said it was politically motivated. The Trump organization on Thursday accused district attorneys of using Mr Weisselberg “as a pawn in a scorched earth effort to harm the former president,” adding that neither the Internal Revenue Service nor other prosecutors would pursue the charge.

Mr Weisselberg and his son Barry on the night Donald Trump won the 2016 presidential election.

Photo:
Jennifer Weisselberg

Prosecutors’ focus on Weisselberg, 73, highlights his central role in the Trump Organization. While Mr. Trump is intricately involved in marketing and anything that involves his image, he trusts Mr. Weisselberg, said Tristan Snell, a former New York assistant attorney general who led an investigation into Trump University that resulted in a $25 million settlement in 2016. Trump, then president-elect, said he decided to focus on running the country.

“It’s always been Trump and Allen,” said Mr Snell. “He is the center of all of this.”

Mr Weisselberg started working for Fred Trump when Mr Weisselberg was in his 20s in the 1970s, when the company focused on building apartments for middle-class families in Brooklyn and Queens. In 1978, Mr. Weisselberg and his wife, Hilary, bought a house in the village of Wantagh in Nassau County.

In those days, Mr Weisselberg was a quiet and diligent employee who had not earned the younger Mr Trump the full respect, said Barbara Res, who started working for the company in 1980. She said Mr Weisselberg paid the bills, collected the rent. and doing personal work for Donald Trump, who was then building a corporate job in Manhattan.


“It’s always been Trump and Allen. He is the center of it all.’


— Tristan Snell, former assistant attorney general of New York

Res said that Donald Trump called his top employees “killers”, meaning they would do anything to close deals or advance his business. Mr Weisselberg wasn’t a murderer then, he said.

Gradually, Mr. Weisselberg gained power, confidence, and office on the 26th floor of Trump Tower, down the hall from Mr. Weisselberg. Trump, said the former associate.

Mr Weisselberg worked closely with Jeff McConney, a senior accounting executive, and Donald Bender, an outside accountant, said Mitchell Zachary, who worked on Trump’s tax accounts with Mr Bender from 1987 to 1995. The Trump Tower office has an “old boys club atmosphere,” he said. Mr Weisselberg, who is not a certified public accountant, quipped Mr Bender, a longtime Trump accountant, for being a nerd, according to Mr Zachary.

Back then, Mr Weisselberg distanced himself from Mr Trump personally, refusing to take advantage of free companies such as vacations at Trump hotels. “Allen said, ‘I’m not going to use Donald’s facilities,’” recalls Weisselberg’s former daughter-in-law Jennifer Weisselberg, who divorced her son Barry in 2018.

Mr and Mrs Weisselberg in the Oval Office. Mr Weisselberg has worked with the Trump family since the 1970s.

Photo:
Jennifer Weisselberg

In 2005, controllers for each of the Trump Organization subsidiaries reported to Mr. Weisselberg, which requires them to visit him at Trump Tower every three months to discuss the financial information they have submitted for review, Mr. Weisselberg said. Snell. If the controller doesn’t show up, angry emails will fly, Mr. Snell.

“Allen isn’t just a bean counter,” said Mr. Snell. “He is also the primary, if not the main arbiter, whether a particular line of business lives or dies.”

Lawyer Mr. Weisselberg could argue in court that he relied on advice from an outside accountant who did corporate taxes, defense attorneys said.

As the relationship develops, Mr. Weisselberg with Mr. Trump, so is his lifestyle. In 2002, he bought a house in Boynton Beach, Florida, about 15 miles south of Trump’s Mar-a-Lago club, according to property records. Some Friday afternoons, Weisselberg will fly to Florida with Trump on his private plane, people familiar with the arrangement said.

Around 2005, Mr. Weisselberg moved into an apartment on the 21st floor of what became known as Trump Place, on Manhattan’s Upper West Side. “Allen brags all the time that she is so important to Donald that he gives her a luxury apartment in the sky,” Ms. Weisselberg, his son-in-law.

Allen Weisselberg, wearing a white face mask, left court in Manhattan on Thursday.

Photo:
brendan mcdermid/Reuters

Weisselberg said Mr. Weisselberg told him that because he had no expenses, and no need to pay for his house, he could help him, Barry, and their children financially.

The aid includes paying her children’s tuition to Columbia Grammar & Preparatory School, a private school in Manhattan, Weisselberg said. Prosecutors called the school this spring, say people familiar with the matter. A school official has appeared before the jury, people said. A lawyer for the school said they complied with all legitimate requests made by the authorities.

Weisselberg has cooperated voluntarily with the prosecutor’s office, said his lawyer, Duncan Levin.

“Jennifer has been privy to conversations, including with Donald Trump himself, about the payment of certain benefits such as tuition, housing and renovations in lieu of a raise, and he has reported these direct conversations to investigators,” Levin said.

Mr Weisselberg’s lawyers have not commented on the specific allegations.

Barry Weisselberg worked at the Trump Organization, where he ran the Central Park ice rink until New York City ended his contract with the company this year. Prosecutors in April requested records about the arena from Ms. Weisselberg, who got it through divorce proceedings, the Journal previously reported.

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Prosecutors have also been examining whether Barry illegally evaded taxes on benefits such as the apartment, the Journal has reported.

In 2004, after Barry surprised her with an engagement party on the ice rink, Jennifer said Barry walked her across the street to an apartment across from Central Park that was being renovated. “He said, ‘Congratulations, this is a gift from Donald and Melania for our wedding,’ said Ms. Weisselberg.

The couple lived in the apartment for about six years starting in 2005, Barry Weisselberg said in a 2018 deposition for his divorce. He said they paid no rent and called it a “corporate apartment.”

An attorney for Barry Weisselberg did not immediately respond to a request for comment.

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Write to Corinne Ramey at Corinne.Ramey@wsj.com

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