When Allen Weisselberg’s son got married in 2004, Donald Trump offered the young couple a generous wedding gift: use of an apartment, overlooking Central Park, rent-free.
Market rent on the apartment, owned by the Trump Organization, would have totaled hundreds of thousands of dollars over the seven years the couple wound up living there. The move — carrying tax implications as well as benefits — in some ways brought the family nearer to the living arrangements of Trump’s own children.
The unusual deal is one of several that benefited the family of Weisselberg, Trump’s right-hand man on all matters financial.
Squat, bespectacled and mustachioed, Weisselberg once handled finances for Trump’s father. Donald Trump and Allen Weisselberg are contemporaries — only a year apart in age — but their relationship evolved over the years as Weisselberg went from helping a young Donald navigate the patriarch’s business to standing by his side as Trump ascended to the top role. These days, Weisselberg is the Trump Organization’s trusted chief financial officer, the only non-family member to help oversee the trust set up by the president while he’s in the White House.
For years, Weisselberg commuted from a simple Long Island home in Wantagh to his office in Trump Tower, a far cry from the boss’s splashy lifestyle. That began to change in the early 2000s, with the Weisselbergs becoming more closely knit with the Trumps in ways unusual for an owner and his CFO, detailed in hundreds of pages of legal, financial, property and tax records reviewed by Bloomberg News.
Many transactions were indirect, benefiting Weisselberg family members. Weisselberg’s younger son acquired a unit in the same Central Park building where his brother received years of free rent and flipped it within a few years for more than three times the purchase price. The elder son, Barry Weisselberg, who works for the Trump Organization, went on to occupy yet another apartment where he didn’t pay rent in a Trump brownstone that has received scant attention.
Weisselberg’s sister-in-law was hired by the business to do compliance work. And Donald Bender, the Trump Organization’s accountant, handled tax preparation services for members of the family. While it’s unclear who paid, tax attorneys found the preparer’s dual role unusual.
In Trump’s world of pricey condo towers and hotels, some of the transactions may seem small. But they map a blurry line between personal and company matters, with assets allotted to the most important employee outside the Trump family.
What’s more, the property transactions exist in a muddy middle-ground between gifts and compensation, and most would have tax implications, lawyers say. Barry Weisselberg worked for Trump in the ice rink business in New York, and his use of the apartments could be considered either a gift for Trump’s tax purposes or additional income for the son on top of his salary.
Tax and compensation lawyers who reviewed the transactions, but did not want to comment about the Trump business, said that as a rule, employers can’t take the gift exemption for things of value provided to employees. Most things of value, like free rent, are taxable income for employees unless an exception applies. A review of the young couple’s tax returns for four of the years they lived on Central Park South don’t flag the perk.
Many of the financial documents were provided to Bloomberg by Jennifer Weisselberg, who was married to Barry Weisselberg from 2004 until an acrimonious 2018 divorce. Post-judgment proceedings continue in New York Supreme Court.
Jennifer Weisselberg said much of the couple’s living costs had been covered by Trump’s company and her father-in-law. Financial statements submitted to the court show that her in-laws covered expenses such as rent and tuition immediately leading up to the separation.
Mary Mulligan and Tim Haggerty, attorneys for Allen Weisselberg at Friedman Kaplan Seiler & Adelman LLP, and Alan Garten, general counsel for the Trump Organization declined to comment for this story. Barry Weisselberg didn’t respond to requests for comment.
The wedding gift offer of the apartment at 100 Central Park South came months before the young couple wed. After they arrived in early 2005, they paid only utilities — delivering checks to Trump’s assistant Norma Foerderer — for seven years.
Jennifer remembers the bill running about $400 a month. When the Weisselbergs moved out, the apartment was listed as a rental for $4,950 a month. It sold for $2.5 million in 2016.
During divorce proceedings, Barry Weisselberg described it as a corporate apartment. He’s a manager of the Trump-run Wollman Rink in Central Park.
The designation as a corporate apartment could be problematic for tax purposes. At seven years, the couple’s use wasn’t for temporary housing. Under federal tax law, lodging generally must be offered as a condition of employment if the value is to be excluded from wages. Barry Weisselberg held the rink job before and after his time at the apartment.
Bender served as accountant for both the Trump Organization and members of the Weisselberg family. “As a matter of firm policy and professional rules, we do not comment on the work we conduct for our clients,” Ian Duncan, chief marketing officer for the firm, Mazars USA LLP, said in response to emailed questions about the transactions.
Even before the wedding gift, Trump transferred an apartment on the building’s fifth floor to Allen Weisselberg and his wife, Hilary. Although city records show no sale price, they list a state transfer tax of $610 in 2000, which would suggest the Weisselbergs purchased the one-bedroom unit for about $152,000. Many of the units in the building needed renovation. They sold it to their younger son, Jack, for $148,000 three years later.
In 2006, Jack sold it for $570,000. He later joined Ladder Capital, which became one of Trump’s largest lenders, though people familiar with the matter say he wasn’t involved in Trump financing. Jack Weisselberg didn’t respond to requests for comment.
Other people in Trump’s innermost circle have made their homes in the company’s properties. In 2016, Bloomberg
Around the time that Allen Weisselberg’s sons moved into the Central Park South apartments, the chief financial officer emerged from his modest surroundings. In 2002, he and his wife bought a Florida home a short drive from Mar-a-Lago. Typically press shy, he made an awkward appearance on Trump’s show, “The Apprentice.”
He and his wife moved from their Long Island home to an apartment in a Trump building on Manhattan’s Upper West Side along the Hudson River. The monthly rent on a two-bedroom unit in the building was recently listed at $7,000. (The building isn’t owned by Trump and has since removed his name.)
During Barry Weisselberg’s divorce in 2018, the Trump Organization provided an additional apartment on which the couple didn’t pay rent. It isn’t clear how the unit’s use was treated for tax purposes.
That apartment is in one of two townhouses on Manhattan’s Upper East Side where Trump has maintained a long-term lease that has gone mostly unnoticed. Though most of the buildings’ units have been rented to others, one hasn’t been for long stretches during the last two decades: the second floor unit at 163 East 61st Street.
Jennifer Weisselberg remembers being told by both her ex-husband and a Trump Organization executive who managed the property that the apartment, a few blocks from Trump Tower, had sometimes been visited by Trump himself. The table had a small TV of the kind he favors for watching cable news, paired with a phone. There was a four-poster bed with Roman columns and gold curtains.
“It was his style,” she recalled.
It’s currently listed for rent at $3,500 a month — furnished.
