Allen Weisselberg stands behind the Trump family, in between Donald Trump and his son Don Jr., right, on Jan. 11, 2017, shortly before the elder Trump moved into the White House.
TIMOTHY A. CLARY/AFP via Getty Images
The Trump Organization is currently on trial in a New York court, charged with 10 criminal counts, including conspiracy and fraud stemming from an off-the-books payment scheme. The star witness in the proceedings is Trump’s former chief financial officer, Allen Weisselberg, who already pleaded guilty to personal charges accusing him of the same crimes. In exchange for the promise of receiving a prison sentence of five months, he agreed to testify in the trial against his longtime employer, taking the stand last week.
Weisselberg, who started working with Donald Trump’s father Fred in 1973 before joining the younger Trump in 1986, might know more about the Trump way of doing business than anyone else, having witnessed it up close for nearly a half century. Much of what he knows is not going to come up at trial. Weisselberg was around when Fred reportedly transferred much of his fortune to Donald, as well as when Donald shaved off small slices for his eldest three children, Don Jr., Ivanka and Eric. In fact, Weisselberg may have even served an example for Donald Trump, who transferred properties to his children in much the same way that Weisselberg shifted an apartment to one of his kids.
The series of deals started in 2000, when Trump’s money man purchased an apartment on the south end of Central Park from Donald Trump for roughly $150,000, apparently about half as much as the place was worth at the time. It remains unclear whether Weisselberg reported the discounted deal as part of his compensation package. His lawyer, Nicholas Gravante, declined to comment.
Records show that Weisselberg kept the apartment—at least for three years. In 2003, he sold the unit to his son, Jack, who was 25 years old at the time, for a little less than $150,000. Jack Weisselberg borrowed $140,000 from JPMorgan Chase and apparently made a down payment of $8,000 to complete the purchase. It wasn’t much of a risk—the value of the property had increased to an estimated $425,000 by the time Jack bought it. Jack Weisselberg did not respond to a series of questions, including whether he paid any gift taxes related to the 2003 sale. In 2006, the younger Weisselberg offloaded the apartment—this time at market rate—for $570,000, giving him an estimated windfall of $430,000.
Trump then followed suit, adding some sweetener in deals with his own kids. In 2004, Donald Trump Jr., the eldest of Donald Trump’s five children, purchased an apartment for $990,000 in a Trump-branded building at 220 Riverside Boulevard on Manhattan’s west side. Tweaking the Weisselberg model, Donald Trump appears to have given his son all the cash he needed—and then some—so that Don Jr. did not have to put down his own money or borrow from a bank. Newly released documents show that Donald Trump listed a receivable on his balance sheet connected to “Don” and “220 RB” for $1,050,000—$60,000 more than the cost of the apartment. In July 2010, Don Jr. sold the unit to a model for $1,845,500. Don Jr. therefore received a windfall of roughly $800,000, even though he apparently did not have to invest any of his cash up front. He repaid the loan against that unit and got rid of part of the debt on another apartment, where the records suggest he owed his father an additional $1.4 million.
Ivanka, the next-oldest Trump child, received similarly favorable treatment. A few months after Don Jr. purchased his apartment on Riverside Boulevard, Ivanka bought a unit in a building named Trump Park Avenue for $1.5 million, receiving a discount of roughly $1.1 million. The money for her purchase also apparently came from her father. Donald Trump’s financial records list another receivable, for $1.5 million described as “Ivanka (T Park Ave).” As of 2021, the most recent year for which records are available, the documents suggest that Ivanka still had not paid the money back.
Next came Eric. Trump’s third child graduated from Georgetown in 2006. A year later, he bought an apartment in a building named Trump Parc East, located at 100 Central Park South, for $2,036,500. The newly released documents suggest that almost all the money came from his father. Donald Trump listed a receivable on his balance sheet worth $2 million, described as “Eric (100CPS).” Eric Trump later bought another three units nearby, one from an independent party and two at steep discounts from his father. It’s not clear whether he paid any gift taxes on the deals with his dad—like his siblings, Eric Trump did not respond to requests for comment. Eric sold one of the bargain units for more than twice what he paid, netting $379,000. He spent an estimated $410,000 merging the other three, which originally cost him a combined $2.9 million to buy, into a 2,400-square foot penthouse. It is now worth an estimated $6.2 million.
All this intrafamily dealing gave the younger Trumps a leg up in life. But in her 2009 book, “The Trump Card,” Ivanka Trump downplayed the benefits. “I’m paying a mortgage on my apartment, just as my brothers, Don and Eric, pay mortgages on their apartments in other Trump buildings,” she wrote. “Admittedly, I pay my mortgage directly to my father instead of to a bank, but it’s a mortgage just the same.” Not quite. Financial documents indicate that Don Jr. paid off his first loan but maintained another, which he had not paid back by 2021, the most recent year for which records are available. Ivanka and Eric did not appear to have paid off any of the principal on their loans as of 2021, according to the documents. The Trump kids, in other words, seem to have received terms from their father that banks would not be likely to offer. Representatives of the Trump Organization did not respond to questions about the deals.
Today, the heirs have all outgrown their starter apartments. Ivanka and her husband Jared Kushner reportedly purchased a $24 million mansion on Indian Creek Island in Miami recently. Her brothers are nearby, having both moved from New York City to Jupiter, Fla. Eric bought a $3.2 million home while Don Jr. shelled out for a $9.7 million one. Jack Weisselberg, meanwhile, still works out of New York City, according to what appears to be his LinkedIn account, at a firm named Ladder Capital, one of the Trump Organization’s lenders.