Allen Weisselberg Has Been Trump’s Loyal CFO for 20 Years. But Could His Own Sons Get Him To Flip?
Manhattan Prosecutors are leaning hard into the tax returns of the Weisselberg brothers with help from an ex-wife of one.
As it became clearer that Manhattan District Attorney Cy Vance would be expanding his investigation beyond the Stormy Daniels hush money payments to more broadly cover the Trump Organization’s finances, greater attention has now fallen on Allen Weisselberg, Trump’s longtime Chief Financial Officer. He is, quite literally, the guy who knows where all the money went and how they tracked it. According to the Washington Post, Weisselberg once described himself in a deposition as Trump’s “eyes and ears...from an economic standpoint.”
If there was any wrongdoing on Weisselberg’s part, Vance wants to exploit it to gain a way into Trump himself. From there might emerge three broad possibilities: 1) Weisselberg falls on the sword and maintains it was all his fault and Donald Trump isn’t to blame for any of it, or 2) Weisselberg pleads the fifth and says nothing, or 3) Weisselberg flips and testifies that Trump knew and participated in the wrongful schemes. Vance is hoping he can make 3) happen.
But how do you flip a money guy who has been loyal to Trump and his family for over 20 years? It turns out, Weisselberg is already no stranger to cooperating with investigators and prosecutors—and even delivering some damaging blows to Trump as a result. When the New York Attorney General’s office was investigating the Donald J. Trump Foundation, Weisselberg helped establish through his testimony that the charity’s board actually never met and that it had been hijacked by the Trump campaign in violation of non-profit laws that prohibit the mixing of politics and charities. That resulted in Trump having to pay a $2 million penalty.
Similarly, when federal prosecutors began to investigate money payments made to keep Stormy Daniels quiet, Weisselberg agreed to a deal to cooperate in exchange for immunity from prosecution. He pointed the finger at others within the Trump Organization, including Michael Cohen who received reimbursements for those hush money payments. In doing so, Weisselberg helped throw Cohen into his own legal quagmire, which later led him to cooperate with authorities.
Thus, Vance knows that it’s possible to get Weisselberg to work with the investigation; there just has to be the right leverage.
And leverage is what Vance is now seeking. There are a few tantalizing ways into cracking Weisselberg that have already been reported, and in a plot worthy of a Shakespearean play, most have to do with his children. His elder son Barry manages Trump properties in Central Park, including two ice rinks that are curiously all-cash businesses, even in 2021. His second son Jack works at Ladder Capital, which has been a big lender to the Trump organization. Prosecutors are actively digging into whether there was anything improper or unusual about Jack Weisselberg’s position there. They may have a lot to work with: Ladder Capital loaned over $270 million to the Trump Organization in connection with four buildings in Manhattan.
Then there is the estranged former daughter-in-law, Jennifer Weisselberg, who went through a messy divorce with the elder son Barry in 2018 and is now actively cooperating with Vance’s office. She told NBC News just this week that she has met with Manhattan prosecutors “multiple times” and turned over documents to them.
In these complex cases, investigators typically deem it critical to have an insider explain not only who was in charge of what and how things operated, but to give a character assessment of key actors such as Allen Weisselberg, the self-proclaimed “eyes and ears” for Trump. Jennifer Weisselberg may be able to provide valuable insights into her father-in-law’s psyche around Trump. She has told prosecutors, for example, that Donald Trump was the absolute center of Weisselberg’s universe. “It absolutely defines who they are,” she said. “Allen would not take an hour or day off if Donald was in the office because I think he felt like he had to be there all the time.”
According to her account, the CFO may be tough to crack. “His whole worth is ‘Does Donald like me today?’ It’s his whole life, his core being. He’s obsessed. He has more feelings and adoration for Donald than for his wife,” she told the New Yorker in an interview. Asked if Allen Weisselberg would flip under pressure, she said, “I don’t know. For Donald, it’s a business. But for Allen it’s a love affair.”
Allen Weisselberg determined his own self-worth by what Trump “thinks about him, about saving him money regardless,” she said to NBC. In this sense, Weisselberg resembles others within Trump’s universe, like Michael Cohen and Paul Manafort, whose allegiance to Trump was finally tested to see if it was stronger than their instinct for self-preservation.
One possible path to squeezing Trump’s CFO is, once again, income tax fraud. According to Business Insider and other reporting, Jennifer and Barry Weisselberg lived in a luxury NYC corporate apartment provided to them by the Trump Organization...rent free. Jennifer Weisselberg claims they only paid utilities on the apartment—around $400 per month. Jennifer believed it was a “gift” on their wedding day from the Trumps. But it was also a way to buy their loyalty. Within the Trump Organization, she explained to the New Yorker, “only a small part of your salary is reported.” She elaborated, “They pay you with apartments and other stuff, as a control tactic, so you can’t leave. They own you! You have to do whatever corrupt crap they ask.”
“It's not easy to walk away when they provide your home,” she told NBC.
That home is what prosecutors hope to show was actually a fringe benefit of Barry Weisselberg’s job, and that he should have been reporting the free rent as income on his taxes. If he didn’t, that could open him up to pressure and even criminal liability, though whether it rises to intentional tax evasion is harder to prove.
The apartment eventually sold in 2014 for $2.85 million, and the signature on the deed is Donald J. Trump.
Jennifer Weisselberg provided one more Donald Trump anecdote that would be amusing if it weren’t so revolting. When Allen Weisselberg’s mother passed away and the family was sitting shivah in their Long Island home, Trump appeared at the event and began to show mourners photos of naked women who had been on his yacht.
“After that, he starts hitting on me,” she told the New Yorker.
Allen Weisselberg, rather than being offended for her, humored his boss and didn’t bother to stand up for her.
I often think about what it would have been like if the prosecutors in NY had done their job decades ago, and gone after trump and others like him (wealthy, corrupt, obnoxious white guys) instead of looking the other way? If they had, trump and his family would be in prison, broke or both, long before he ever ran for President. Not going after white collar criminals, has far reaching consequences.
Two comments. 1) There is no way Barry didn’t know he should have reported rent value on his income tax statement. I lived in a house provided by a church for years, and we always had to claim that rent value as income. We would have been sent to prison if we didn’t claim it. Our tax burden was outrageous for the puddly salary we got but we did the right thing and paid up. No self-respecting accountant would let somebody get by without reporting. 2) I just watched “Pose”, and part of the story line there was like it was lifted from your writing about this, Jay. Couldn’t believe they even used trmo’s name in the series.