‘Like a Mob’: Prosecutors Look at Trump’s Ice Rink Man

Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty
Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty
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Ever since New York prosecutors hit the Trump Organization and its top financial officer, Allen Weisselberg, with tax fraud charges in July, it’s been obvious they have more evidence of wrongdoing than they’ve laid out. But now, it’s certain: Prosecutors also have evidence that the executive’s son, Barry Weisselberg, received the very same kind of corporate perks that investigators allege should have been taxed as income.

Barry Weisselberg is the longtime manager of the Trump-owned Wollman ice rink in Central Park. Details about the financial arrangement, as well as tax returns showing that the additional income was unreported, were delivered to the New York attorney general and Manhattan district attorney by Barry Weisselberg’s ex-wife, Jennifer Weisselberg. And The Daily Beast has reviewed the material, which includes a decade of tax returns and statements of net worth.

As Barry Weisselberg explained in a deposition when his finances were under a magnifying glass in his divorce case, the Trump Organization owned the one-bedroom flat in Manhattan’s expensive Upper East Side where he lived in 2018.

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“It’s a corporate apartment that I was given temporarily,” he testified under oath in August 2018, adding that he had no clue if rent was being paid.

That deal was described as a tax-dodging “scheme to defraud” in the June 3 indictment against the Trump Organization and his father, the company’s chief financial officer. In it, prosecutors said the pad had “no reported rent at all.” The indictment noted that the company “intentionally failed” to report that income or pay associated taxes to federal, state, and local government agencies.

“The value of the lodging provided to [Allen] Weisselberg’s family member constituted income to that family member,” the indictment reads.

Barry Weisselberg was not named in the indictment, but he is the only person who matches the document’s description of a male Weisselberg family member who works at the company and lived there during that time.

Investigators are also examining how the company paid for two Weisselberg children to attend the Columbia Grammar and Preparatory School. Although the indictment focuses on how grandpa was allegedly on the hook for getting $359,058 in tuition payments from 2012 to 2017 without it appearing on his taxes as additional salary, the checks that Donald Trump allegedly signed himself benefited Barry Weisselberg’s kids.

But there are other corporate perks not mentioned in the indictment that could become fodder for investigators. There’s the “corporate discount” that Barry Weisselberg got to station his car at a Quik Park parking garage, which he referenced in his divorce deposition as well. Prosecutors could also take a closer look at whether the Trump Organization used Allen Weisselberg to pass untaxed benefits through to his son.

In his divorce, Barry Weisselberg testified that his father paid the leases for his 2015 Lexus RX 350 and his 2018 Range Rover Velar—though his ex-wife maintains that these were company-provided cars.

“It’s all about control. The apartment, the car, the parking garage, the tuition, your vacations, your life, really,” Jennifer Weisselberg told The Daily Beast. “You’re embedded with them. You’re indebted to them… when you work there, you end up doing crimes.”

“You’re stuck. It’s like a mob. It all stays quiet because they end up owning you,” she said.

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But if you were wondering why the ice rink manager has not yet been indicted alongside his father, part of the problem appears to be timing.

Some of the lowest-hanging fruit to charge Barry Weisselberg with is actually overripe. The state’s five-year statute of limitations has passed on a potential felony charge involving his company-funded stay at a previous luxury apartment overlooking Central Park, because he left the apartment in 2012. The renovations and rent-free perks there could add up to more than $400,000 in additional income that allegedly went untaxed, but it’s too late for the government to pursue that case.

Rent or mortgage payments there would have easily amounted to more than $60,000 a year, as the unit eventually sold for $2.5 million, according to a Bloomberg investigation that first revealed the deal. But as Weisselberg also explained in his divorce deposition, the unit at 100 Central Park South “was a corporate apartment, so we didn’t have rent.” His ex-wife has told prosecutors that the apartment was a 2004 wedding gift whose continuous rent payments were made from the Trump Organization in lieu of salary raises.

This arrangement was also mentioned in the indictment, but again Barry Weisselberg was not identified by name.

Were this a civil case instead of criminal investigation, Barry Weisselberg could still be sued, because the alleged fraud was only recently discovered, explained Daniel L. Feldman, a professor at the City University of New York's John Jay College of Criminal Justice.

It’s unclear if prosecutors are using the threat of an indictment against Barry Weisselberg to force his father to cooperate and turn on Donald Trump himself, who remains the ultimate target of the investigation, according to three people familiar with the investigation who spoke to The Daily Beast on condition of anonymity.

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Allen Weisselberg is the highest-ranking executive with a close relationship to Trump spanning decades who is not an actual member of the Trump family. The bond of trust was strong enough that the day before he started his presidency in 2017 Trump appointed Allen Weisselberg to run the entire company alongside Don Jr.

Both the Manhattan DA and New York AG declined to comment. Barry Weisselberg did not respond to text messages and emails requesting an interview.

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