New York prosecutors have subpoenaed an elite private school in Manhattan as part of an investigation into former President Donald Trump and his Trump Organization, according to the Wall Street Journal.
Sources told the Journal that Columbia Grammar & Preparatory School was subpoenaed by prosecutors in the Manhattan District Attorney’s office.
Jennifer Weisselberg – the childrens’ mother – previously told Insider that Trump would include school tuition in the compensation package for her former husband, Barry Weisselberg. She is a cooperating witness in investigations from both the Manhattan District Attorney’s office and the New York Attorney General’s office.
Prosecutors may be examining whether the tuition arrangement allowed Barry or Allen Weisselberg to avoid paying taxes, according to the Journal.
Jennifer Weisselberg told the Journal that more than $500,000 in tuition was paid for with checks written either by Trump or Allen Weisselberg. But the records in her possession don’t show who made the payments, the Journal reported.
The subpoenas for the elite Upper West Side school will allow prosecutors to obtain copies of the transactions for tuition payments, which may tell them whether they came from Trump, Allen Weisselberg, Barry Weisselberg, the Trump Organization, or some other source.
Prosecutors in the Manhattan District Attorney’s office have already gone to the Supreme Court to subpoena reams of financial documents from the Trump Organization, including tax filings. They have also subpoenaed Allen Weisselberg’s bank records.
The Trumps and Weisselbergs have ties to Columbia Grammar
Michael Cohen, a former executive at the Trump Organization and personal lawyer for Trump, was previously the chairman of Columbia Grammar’s board. He helped make sure the Weisselberg grandchildren would be considered for admission, Jennifer Weisselberg previously told Insider.
The children of Jack Weisselberg, Allen Weisselberg’s other son, have also attended Columbia Grammar, according to the Journal.
Barron Trump, the former president’s youngest son, attended the school when he lived in New York City.
And the Trump Foundation – Donald Trump’s now-dissolved charity organization – donated $150,000 to the school between 2014 and 2016, according to the Journal’s review of tax filings.
James’s office is conducting its own investigation into Trump’s and the Trump Organization’s finances. It has made fewer public moves than the investigation from Manhattan District Attorney Cyrus Vance Jr. Vance is set to retire in December, and is widely expected to make a decision about whether to bring charges against Trump or the Trump Organization before then.
Trump faces numerous other legal headaches, including investigations into his conduct as president, lawsuits over sexual misconduct allegations, and an investigation in Georgia into his attempts to overturn the 2020 election results there.
In an earlier interview with Insider, Jennifer Weisselberg said the Trump Organization would pay employees like her former husband with perks like tuition and housing instead of cash as a way to control their lives.
“They want you to do crimes and not talk about it and don’t leave,” she said.
The Manhattan District Attorney’s Office, which was scrutinizing the company’s finances, reportedly attempted to “flip” Weisselberg as part of its investigation.
During the 2015 deposition, Weisselberg answered questions about how much he knew about potential wrongdoing the company, the Daily News reported. He was “eavesdropping” on some legal-related conversations but backed away, the report said.
He reportedly said: “Throughout all of our entities, people do know it’s important to involve me when it comes to financial matters 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.”
Insider has reached out to The Trump Organization for comment.
The attorney, Duncan Levin, said in an interview that he was hired to conduct his own analysis of the reams of documents Weisselberg has, which include Trump Organization financial records and show how intertwined the company is with the Weisselberg family’s finances.
“We’re basically culling through it methodically, and we will turn over documents and information to law enforcement as is helpful,” Levin said.
Weisselberg has been speaking with prosecutors in the Manhattan District Attorney’s office and the New York State Attorney General’s office as they investigate the finances of both Trump and the Trump Organization. The offices appear to be running parallel investigations into whether the former president and his company misrepresented the values of properties and other assets in order to pay less in taxes and procure favorable loan terms.
“They picked up documents many times. They ended up taking seven boxes of my documents and scanning them, going through them,” she said, adding that “they took depositions, they took checks, routing numbers, bank-account [information], and things like that.”
Vance’s investigation in particular appears to be heating up. Shortly after Trump left office, Vance hired Mark Pomerantz, a seasoned prosecutor of white-collar crimes and mob bosses, to help the investigation. Pomerantz has interviewed Jennifer Weisselberg several times, she told Insider. And Vance is widely expected to bring indictments before he leaves office at the end of this year.
“It was my distinct impression that things are heating up and that this investigation is of intense focus for prosecutors at the DA’s office,” Levin said. “They are staffed up and ramped up to investigate every aspect of this that they can.”
Levin, now a partner with his firm Tucker Levin PLLC, worked as the head of the Asset Forfeiture division for Vance between 2011 and 2014. Prior to that, he held positions as a prosecutor at the US Attorney’s Office for the Southern District of New York and in private practice with Vance, along with an earlier stint at the Manhattan DA’s office under Vance’s predecessor, Robert Morgenthau.
Together with a forensic accountant, Levin said he’s sorting through the remaining documents in Weisselberg’s possession.
“I’ve been building complex financial fraud cases for 20 years now,” Levin said. “I have been in close contact with the prosecutors’ offices. We have indicated to them that we are going through these documents in a very sophisticated way.”
“I can’t comment on any specific documents that may or may not belong to the Trump Organization, but I can say that the source of funds for their lifestyle was largely from the Trump Organization,” Levin said.
“They picked up documents many times. They ended up taking seven boxes of my documents and scanning them, going through them,” she told Insider, adding: “They took depositions, they took checks, routing numbers, bank account [information], and things like that.”
But an earlier peek into those finances came in September, when Jennifer Weisselberg handed her documents over. Weisselberg was married to Barry Weisselberg, the son of Trump Organization CFO Allen Weisselberg, between 2004 and 2018. Barry Weisselberg is also a key employee of the Trump Organization in his own right, managing the Wollman Rink in Central Park in Manhattan.
Barry Weisselberg initially withheld financial information from Jennifer during divorce proceedings, she said. The divorce judge recognized perks he received from the Trump Organization – like their shared apartment – could have monetary value and should be considered during divorce negotiations, she said.
“The judge said there was a lot of imputed money,” Jennifer Weisselberg said. “They subpoenaed a lot of things after Barry’s deposition.”
An attorney representing Barry Weisselberg didn’t immediately respond to Insider’s request for comment.
‘I don’t think they realized that I had that stuff’
Donald and Melania Trump gave Barry and Jennifer Weisselberg an apartment in the Trump Parc East Building in Manhattan as a wedding gift. It was part of many perks the Trump Organizations offered members of the Weisselberg family, as reported by Bloomberg’s Cabe Melby in November.
Following the publication of that article, investigators in the New York Attorney General’s office expressed renewed interest in the documents Jennifer Weisselberg gave them, she said.
“Since the Bloomberg article came out – I don’t think they realized that I had that stuff,” Weisselberg told Insider. “The AG came and they started picking up more boxes.”
“It’s so controlling,” she continued. “Because if you want to leave and make the same money – you live there. If you want to leave, where are you going to live?”
Jennifer Weisselberg said she’s now glad to have left Trumpworld.
“I don’t want anything to do with them,” she said. “I don’t want their money. I’m good.”
Prosecutors in the Manhattan DA’s office are now interested in “flipping” Allen Weisselberg to guide them through the millions of documents they’ve obtained, according to The Washington Post. They are looking into whether perks like the apartment broke tax laws, according to Bloomberg.
The office recently hired Mark Pomerantz, who has experience as a prosecutor pursuing mob bosses. It also sent a forensic accountant with experience analyzing mob finances to review Jennifer Weisselberg’s documents, she said.
Representatives for the Trump Organization didn’t immediately respond to a request for comment for this story. Representatives for Allen Weisselberg, the Manhattan DA’s office, and the New York Attorney General’s office declined to comment.
The former wife of a key Trump Organization employee scrutinized by prosecutors said the company holds sway over employees through unusual financial arrangements, including paying for her home and tuition for her children.
The office successfully subpoenaed millions of pages of tax documents from the Trump Organization in February. Prosecutors there are now seeking to “flip” Allen Weisselberg into guiding them through those pages, the Washington Post reported.
Jennifer Weisselberg says the company retains a grip on key employees by withholding raises. In yearly compensation meetings with Barry Weisselberg, she said, Trump or Allen Weisselberg would offer to pay the tuition of their children instead of giving raises. She said her ex-husband’s base salary didn’t change substantially in the roughly 20 years he’s worked there.
“It was like Allen designing a plan,” she said. ‘It was like, ‘Okay, the way we’re going to maestro this is instead of a raise, we’re going to pay my daughter’s tuition. Instead of a raise, we’re going to pay for the apartment.'”
‘If you want to leave, where are you going to live?’
Donald and Melania Trump gave Jennifer and Barry Weisselberg an apartment in their Trump Parc East building by Central Park in Manhattan as a wedding gift, as Bloomberg News first reported. The couple paid only $400 per month in utilities and other fees – far below the market rate for rent. Prosecutors are examining whether the way the arrangement was reported in tax documents violated tax laws, according to Bloomberg News.
“Obviously, it’s not a gift when you get the same salary for 20 years,” she said.
“It’s so controlling,” she continued. “Because if you want to leave and make the same money – you live there. If you want to leave, where are you going to live?”
Since Allen Weisselberg handled the finances for both the Trump Organization and her family, gifts like that also served as a way to avoid paying taxes, Jennifer Weisselberg said.
“That’s the compensation. They just pay for everything, instead of paying on the books,” she said. “It was a way Allen decided to [benefit] Donald, or to avoid employee taxes, state taxes, gift taxes. I mean, if you want to get compensated and thank Donald – great. But you got to pay taxes on it.”
Representatives for the Trump Organization and for Barry Weisselberg didn’t immediately respond to a request for comment for this story. Representatives for Allen Weisselberg, the Manhattan DA’s office, and the New York Attorney General’s office declined to comment.
The mustachioed, press-shy Allen Weisselberg has served as the Trump Organization’s Chief Financial Officer for decades, as well as Trump’s personal bookkeeper. Now, he’s reportedly the subject of a wide-ranging inquiry from the Manhattan District Attorney’s office.
Weisselberg knows more about the Trump Organization’s finances than anyone else
Weisselberg got his start with the Trump family in the 1970s as a bookkeeper for Fred Trump.
Over the years, he ascended the ranks of the Trump Organization to become its chief financial officer, and has held the keys to the family’s financial life, as well. (While other reports refer to him as an accountant, Weisselberg does not hold a CPA license, according to New York state records.)
“There’s a misconception about The Trump Organization that it’s this big, massive company with 10,000 employees,” Michael Cohen, Trump’s former personal lawyer and a vice president for the Trump Organization, said in Congressional testimony. “It’s not. I mean, the entire company was really run by 12 of us.”
Weisselberg’s name made headlines in 2018 and 2019 as federal prosecutors investigated Cohen’s hush-money payments ahead of the 2016 election to women who accused Trump of having affairs with them.
Cohen released a tape purporting to show Weisselberg discussing how to facilitate the payments and what they might mean for the Trump Organization. And while Cohen ultimately pleaded guilty to federal crimes in connection with the scheme, The Wall Street Journal reported Weisselberg himself received immunity for cooperating with the investigators in the Southern District of New York who prosecuted Cohen, avoiding charges.
While the Manhattan District Attorney’s office likely has all the documents they need for their investigation, Jeff Robbins, a former federal prosecutor who oversaw money-laundering investigations, said that having someone like Weisselberg guide them through all the evidence could be enormously helpful.
“I’m sure the records have been turned over by the hundreds and thousands,” Robbins told Insider. “However, it sure makes it a lot easier if you have somebody who can walk the prosecutors through the documents and explain the sequence, and who would have had direct conversations with Trump.”
Unlike Donald Trump Jr. and Eric Trump, two of Trump’s eldest children who play leading roles in his company, Weisselberg has made few forays into politics. New York state voter registration records reviewed by Insider show that he’s a registered Republican living in Manhattan’s Upper West Side (the building previously carried Trump branding that has since been removed), but he didn’t donate to any of his boss’ presidential campaigns.
Weisselberg also donated to former Illinois Rep. Dan Rostenkowski, a Democrat who led the House’s powerful Ways and Means Committee, in 1994. The donation came a month before Rostenkowski was criminally indicted for his role in a corruption scandal that ultimately led to his resignation and a guilty plea on mail fraud charges.
Weisselberg and his wife have a home, a short drive away from Trump’s Mar-a-Lago club, in Boynton Beach, Florida. They’re currently involved in a lawsuit with their homeowner insurance company over damage following 2017’s Hurricane Irma.
Mary Mulligan, an attorney representing Weisselberg at Friedman Kaplan Seiler & Adelman LLP, declined to comment for this story.
His family’s financial ties with the Trump Organization go into legal gray areas
The Trumps have always seemed to have a porous wall between their personal finances and their businesses and foundations. In 2019, Trump paid $2 million to settle a lawsuit the New York Attorney General’s office brought, alleging he used resources from The Trump Foundation to boost his political fortunes.
These gray areas reportedly extend to Weisselberg and his family. And they also run into possible legal conundrums.
In November 2000, according to Bloomberg News, Trump gave a unit at Trump Parc East, a condominium building at 100 Central Park South, to Weisselberg and his wife, Hilary. Records reviewed by Insider show it had a sale price of $152,500, an eye-poppingly low price for prime Manhattan real estate.
The couple sold it to their son Jack Weisselberg in 2003 for $148,000, who sold it for $570,000 in 2006, Bloomberg News reported.
Barry Weisselberg, another one of Allen Weisselberg’s sons, has even closer and more complicated financial ties with the Trumps. He’s an employee at the Trump Organization, having managed the Wollman ice skating rink in Central Park, which until recently was run by the company through a contract with New York City.
He, too, received an apartment at the Trump Parc East building. According to Bloomberg News, Barry and his now-ex-wife Jennifer Weisselberg received it as a wedding gift in the mid-2000s from Trump and paid for only utilities, at around $400 per month. When the couple moved out, it was rented out for nearly $5,000 per month, and a Trump-owned entity sold it for $2.8 million in 2014, according to Bloomberg.
But while Barry and Jennifer Weisselberg both lived there, Barry listed it as a corporate apartment in his divorce proceedings, Bloomberg News reported. Their tax returns, though, according to Bloomberg News, didn’t always list the apartment as a corporate perk. The designation may mean that Barry Weisselberg and the Trump Organization itself may have not paid the correct amount of taxes on the apartment, Bloomberg’s Caleb Melby reported.
“On the question of where Allen Weisselberg stands in the evidence pyramid, he stands right below Donald Trump himself,” Robbins, now an attorney at Saul Ewing Arnstein & Lehr, told Insider. “So it does appear to be an exploration on the part of the DA’s office as to whether or not they can flip Allen Weisselberg by leveraging one of his two sons.”
The investigation into the Weisselbergs grew out of Vance’s investigation into the Trump Organization’s business dealings with other companies, including Deutsche Bank and Ladder Capital. Jack Weisselberg is also a subject of the probe, though it’s unclear if he had any role in loans Ladder Capitol gave to the Trump organization, according to Bloomberg News.
The Trump Organization also gave Barry Weisselberg an Upper East Side townhouse while he was in the divorce process in 2018, according to Bloomberg News. It isn’t clear how Weisselberg and the Trump Organization treated it in tax filings.
While Allen Weisselberg seems to have been loyal to the Trump family for years, Robbin said the pressure on his family could flip him.
“The likelihood of him cooperating goes up significantly if, in fact, the prosecutors have criminal charges that can reasonably be brought against his sons,” Robbins said. “For the simple human reason that what father would not do something unpleasant in order to help his sons out of a legal jam?”
Apartments seem to be a common perk for Trump employees. Cohen also had an apartment in one of Trump’s buildings while working for the mogul, and former communications director Hope Hicks stayed in one “rent-free” during Trump’s 2016 campaign. Matthew Calamari, Trump’s loyal longtime head of security, also has a home in the Trump Parc East building, according to records reviewed by Insider.
Jake Weisselberg and representatives for Ladder Capital didn’t immediately respond to Insider’s requests for comment. Barry Weisselberg couldn’t be reached for comment. Jennifer Weisselberg didn’t immediately respond to requests for comment.
The CFO testified for federal prosecutors in Manhattan who secured Cohen’s guilty plea. Weisselberg helped the Trump Organization reimburse Cohen the $130,000 hush-money payment he made to Stormy Daniels, the adult film actress who said she had sex with Donald Trump during Melania Trump’s pregnancy.
Weisselberg’s name didn’t appear in the charging documents against Cohen, and he was never charged for his participation in the scheme.
Cohen hasn’t forgiven Weisselberg. When the news broke that prosecutors were looking into Weisselberg’s family, he took to Twitter.
“Remember that Allen Weisselberg received (federal) immunity from the SDNY to provide information and testify against me for the @StormyDaniels payment. #KarmaBoomerang,” Cohen wrote.
Weisselberg told prosecutors he had little knowledge of the Trump Foundation’s operations and testified he had no knowledge that he was on the Trump Foundation’s board of directors in a deposition transcript reviewed by Insider.
He did, however, testify that the foundation was used to boost Trump’s campaign in 2016. James’ office used the testimony in its lawsuit against the Trump Foundation where a judge forced Trump to pay a $2 million fine.
Weisselberg’s vast knowledge of Trump’s finances has made him a target in civil lawsuits, as well.
He was a defendant in a 2017 lawsuit from William Weinstein, a New York resident who sought to create a mechanism to ensure that Trump wouldn’t take foreign profits as president through the Trump Organization. It was dismissed in short order, with the judge ruling that Weinstein didn’t have the standing to sue. Trump has steadfastly refused to release financial records, and The New York Times reported that Trump has paid far more in foreign taxes over the past two decades than in US taxes.
He’s been less helpful in an ongoing investigation from the New York AG
Weisselberg also testified in a different, ongoing investigation into Trump’s finances from James’ office, sitting for a deposition under subpoena in July and August 2020.
“When examined by [the office of the attorney general], however, Mr. Weisselberg testified that he had no first-hand knowledge of this fact, had not reviewed the relevant documents to confirm that any such understanding was true, could not identify any return on which the forgiveness was treated as income, and instead was relying solely upon his recollection of conversations he had years earlier with the Trump Organization’s accountants concerning the tax treatment of the amount of the debt that was forgiven,” the filing says.
The Trump Organization refused to furnish the relevant tax documents, attorneys for the AG office wrote in the filing.