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The old Delmonico Hotel stands on the corner of New York City’s 59th Street and Park Avenue, one of the most prestigious intersections in the United States. Donald Trump purchased the building, with its arched windows and brick facade, for a reported $115 million in 2002 and spent another $85 million or so converting it into luxury condominiums. Retrofitted with Italian fixtures and marble finishes, he rebranded the place Trump Park Avenue. By the end of 2005 he had sold 91 units for $231 million, according to a review of property records—and still had another 31 units to spare. The deal was Donald Trump at his best: recognizing an underperforming asset, dressing it up with some glamour, and selling it to a bunch of big-budgeted buyers.
There was one purchaser, however, who paid a relatively small sum of money. Just months after graduating from the University of Pennsylvania, Ivanka Trump reached a deal with her father for a 1,549-square-foot apartment. The price: $1.5 million, or $968 per square foot.4The other buyers, by comparison, paid an average of $1,667 a square foot, meaning Ivanka got a discount of more than $1 million. It’s nice to be the daughter of the developer.
America’s first daughter, who did not respond to a list of questions sent to both the Trump Organization and the White House, started her career outside of her father’s real estate business. She joined another development firm called Forest City Ratner, working as a project manager for its retail division. A year into that position, longing for more responsibility, she headed home, where her old man was waiting with an offer to become an executive at the Trump Organization. “Being 24 and 28, respectively, we’re able to do things that we never would be able to do,” Ivanka said in a 2006 interview with her brother Don Jr. “So we cut out years of sort of bureaucratic paper pushing.”
Inside Trump Tower, Ivanka also became a television star, joining her father onscreen for The Apprentice in 2006. Not long after, she began to develop her own brand. Her father represented successful, strong men. Ivanka, American heiress, wanted to stand for sophisticated working women. “I remember one of my earlier Christmas gifts was a Barbie, and I was devastated,” she said on the set of Conan O’Brien’s late-night talk show in 2007, “because my brothers had gotten Legos and Erector Sets. So to me, this was traumatic, and I wanted that. So I ended up taking my younger brother’s Legos, bringing them into his room, to add insult to injury, locking him out, taking my mother’s superglue—from the 1980s, there was plenty for her nails— and gluing the Legos together in a model of Trump Tower.”
It was a perfectly crafted tale, one stunningly similar to a story Donald Trump previously told about his brother. “Robert is two years younger than I am,” Trump wrote in The Art of the Deal, “and we have always been very close, although he is much quieter and more easygoing than I am. One day we were in the playroom of our house, building with blocks. I wanted to build a very tall building, but it turned out that I didn’t have enough blocks. I asked Robert if I could borrow some of his, and he said, ‘Okay, but you have to give them back when you’re done.’ I ended up using all of my blocks, and then all of his, and when I was done, I’d created a beautiful building. I liked it so much that I glued the whole thing together. And that was the end of Robert’s blocks.”
Ivanka Trump is Donald Trump but 35 years younger, with an aristocratic air and a feminist twist. After joining the Trump Organization, she technically worked for her older brother, Don Jr., but they operated more like equals.10 And before long, their father began giving clues about whom he considered his heir or, in this case, heiress apparent. In 2007, when Ivanka was just 25, he added her to the board of Trump Entertainment Resorts—passing over her big brother. Ivanka earned $150,000 a year in director fees from the publicly traded company, the same one her father had been bleeding cash from for years. In 2009, days before the business filed for its second bankruptcy in five years, Donald and Ivanka both resigned from the board.
