The Family Secrets Fueling the Trump Organization Indictment

Photo Illustration by The Daily Beast / Photos Getty/AP
Photo Illustration by The Daily Beast / Photos Getty/AP
  • Oops!
    Something went wrong.
    Please try again later.
  • Oops!
    Something went wrong.
    Please try again later.

While the Manhattan District Attorney’s office undertook a years-long, high-stakes battle to obtain Donald Trump’s tax records—twice returning to the Supreme Court—some of the most damning evidence was quietly in the possession of someone who was more than willing to turn it over: the ex-daughter-in-law of a top Trump Organization executive.

Allen Weisselberg, the Trump Organization’s longtime chief financial officer, has always been key to unlocking the finances of the Trump family business. For years, prosecutors have been looking for documents that would show what exiled insiders like Trump’s ex-consigliere Michael Cohen have claimed: that the Trump Organization was fudging numbers and dodging taxes.

What investigators didn’t know was that the proof was in the hands of Jennifer Weisselberg, the woman once married to Barry Weisselberg, the son of Allen Weisselberg. And it wasn’t until November 2020 that city and state investigators connected with her to acquire the evidence.

The Daily Beast has obtained some of the records that, according to Ms. Weisselberg and her lawyer, have proved pivotal to last week’s indictment of the Trump Organization CFO.

Corporate Perks

The top finance executive at the Trump Organization was indicted for dodging taxes by receiving pay in unaccounted corporate perks. Among them: redirecting his salary to cover tuition payments for his grandkids.

As prosecutors would discover, Barry Weisselberg explained it all in sworn testimony he made during a deposition in his divorce case in August 2018.

<div class="inline-image__credit">Official papers</div>
Official papers

Grandpa Weisselberg paid more than $50,000 a year for each of the two kids to attend a top-rated private academy, the Columbia Grammar and Preparatory School. He’d been doing it for at least six years, Barry Weisselberg told his wife’s lawyer, Clifford Petroske.

New York investigators would later ask Jennifer Weisselberg about that financial arrangement, according to two people in the room. They said prosecutors’ eyes widened when she explained that Trump himself would sign a check that she would hand deliver to the school.

That detail made its way into page seven of last week’s indictment: “as part of the scheme to defraud, Trump Corporation personnel, including Weisselberg, arranged for tuition expenses for Weisselberg’s family members to be paid by personal checks drawn on the account of and signed by Donald J. Trump.”

In the indictment, the office of Manhattan District Attorney Cyrus Vance Jr. noted that tuition payments “constituted employee compensation and taxable income to Allen Weisselberg,” but it claims he hadn’t reported that additional $359,058 in his taxes over the years.

Luxury Living On A Budget

The indictment also mentions “a family member” of the CFO who took part in “the scheme to defraud” the government by getting a company apartment—again, without reporting it on personal income taxes.

This, too, stemmed from the Barry-Jennifer divorce case. Investigators found that the CFO’s son, a fellow Trump Organization employee in charge of its Wollman ice skating rink at Central Park, was keeping his official salary artificially low. In his divorce case, Barry Weisselberg testified that he didn’t even get a monetary raise in years, and according to investigators, he received the extra compensation in the form of fringe benefits.

The documents lay it out. Barry and Jennifer Weisselberg’s joint 2010 tax return lists his combined “wages, salaries, and tips” at $132,811. In New York, that’s enough for a couple to live in a comfortable one-bedroom apartment in Queens with a view of the city.

<div class="inline-image__credit">Official papers</div>
Official papers

But in actuality, the Weisselbergs were staying at the ritzy 100 Central Park South, premium real estate at a coveted spot in the heart of Manhattan. The cost of living at the Trump-owned building is several times higher than what Weisselberg could afford on that salary, where monthly rent nowadays ranges from $5,300 to $20,000.

The answer? Donald Trump picked up the tab for more than six years.

“It was a corporate apartment, so we didn’t have rent,” Barry Weisselberg said in his deposition.

His wife’s lawyer kept pressing with questions to reveal the value of this luxurious corporate perk.

“What would the rent have been if that apartment would have been rented to a third party?” Petroske asked.

“I have no idea,” Barry Weisselberg replied.

When asked whether he’d reported the apartment perk on his taxes from 2005 to 2011, he said he didn’t “recall.”

<div class="inline-image__credit">Official papers</div>
Official papers

This is the same arrangement that the longtime Trump ice rink manager had for his next place: a one-bedroom apartment in Manhattan’s expensive Upper East Side, on the same block as the Trump Plaza building.

In his divorce deposition, Barry Weisselberg described this other spot as “a corporate apartment” and said he simply didn’t know who was paying the rent, if it were being paid at all.

<div class="inline-image__credit">Official papers</div>
Official papers

In the indictment, prosecutors said that second apartment also “constituted income” that should have been taxes, but that the Trump Organization “intentionally failed to do so.”

Barry Weisselberg was not charged in last week’s indictment, but the investigation is ongoing and the government could still target him. It’s a looming threat that could be understood as a strategy: applying additional pressure on the CFO, so that he cooperates with law enforcement to spare his son from the probe.

All The Way To The Top

The Manhattan District Attorney and New York Attorney General, which have struck a rare partnership to prosecute this together, have hinted that there’s more to come. Questions asked of witnesses, who spoke to The Daily Beast on condition of anonymity, show that investigators are interested in other executives as well.

And as the current case centers on questions about untaxed “fringe benefits,” the DA and AG will have to prove who tweaked salaries—and whether they knew about tax rules.

Once again, Jennifer Weisselberg’s divorce case shows the path.

Barry Weisselberg’s testified that his pay—which remained flat for “numerous years” while the corporate perks added up—was decided by his own father, Allen Weisselberg, and Trump’s Chief Operating Officer, Matthew Calamari.

Trump’s bodyguard-turned-COO was not named in the indictment, nor has he been charged with a crime. But investigators are probing Calamari’s activity, according to two people familiar with the investigation.

Prosecutors also have reason to examine Trump’s involvement more closely as well. In his divorce testimony, Barry Weisselberg made clear that his pay was once determined by the head honcho himself.

“Personally Donald Trump would make that decision?” his wife’s lawyer asked.

“Yes,” Barry Weisselberg responded.

<div class="inline-image__credit">Official papers</div>
Official papers

Trump only stopped personally overseeing the skating rink manager’s pay when Trump became president of the United States, Barry Weisselberg claimed. If true, that would rope in Trump, who called himself “king of the tax code” for years and is now trying to walk that back and play dumb.

A Familiar Name

In the several boxes of evidence that investigators received from Jennifer Weisselberg, they came across one name they knew well: Donald Bender.

For years, the DA’s office had been seeking Trump’s tax returns held at his trusted outside accounting firm, Mazars USA. The Trump Organization had them prepared by Bender, a partner at Mazars USA’s Long Island office, and always in close consultation with Allen Weisselberg, according to a source familiar with the arrangement.

Jennifer Weisselberg’s records show that Bender also prepared the couple’s taxes back in 2009 and 2010, when he was at a previous iteration of the firm.

<div class="inline-image__credit">Official papers</div>
Official papers

Jennifer Weisselberg’s lawyer, Duncan Levin, credited his client with gifting investigators a mountain of evidence.

“Jen has shown a great deal of bravery in coming forward with the information that she has,” he said. “She has been 100 percent cooperative with prosecutors for many months. She’s met with prosecutors more than a half dozen times, and has really done a thorough job of culling through a huge volume of materials to give to prosecutors. I’m very confident she is a pivotal witness to the district attorney’s office and in large measure responsible for where things stand today.”

Jennifer Weisselberg told The Daily Beast that her guiding principle was the example that her actions would set for her kids.

“Justice matters to me,” she said. “I always wanted to teach my kids right from wrong. Accountability. And that if you don’t cheat and lie, you can still succeed with dignity.”

Read more at The Daily Beast.

Get our top stories in your inbox every day. Sign up now!

Daily Beast Membership: Beast Inside goes deeper on the stories that matter to you. Learn more.