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Clash of the Utopias

Rob was handed more acquisitions. In 1999, he led a team that bought Colgate’s headquarters at 300 Park Avenue in a $225 million deal. Rob devised a plan to retrofit the building’s garish pink exterior with bigger windows and a modern aluminum skin. Today, one source said, the property has been appraised at $1 billion.

In January 2004, he bought the Philip Johnson–designed Lipstick Building at 885 Third Avenue for $230 million. In November 2004, he snapped up the former New York Times Building for $175 million (he flipped it two and a half years later for $525 million). Rob’s ascent through the Tishman Speyer ranks coincided not only with the expanding real-estate bubble but also with a time of generational transition for the city’s leading real-estate families and the arrival of a new player in town: Jared Kushner, the 28-year-old scion of disgraced New Jersey developer and political donor Charles Kushner. Industry observers couldn’t help but note a potential rivalry. “You had a situation where both fathers wanted their sons to come out,” says one senior real-estate executive. “In the case of Kushner, it was a chance to redeem himself and have his son rise above his [father’s] problems.” In March 2005, Charles Kushner was sentenced to 24 months in jail for tax violations and his attempted plan to blackmail his brother-in-law by hiring a prostitute to seduce him while being videotaped. With his father behind bars, Jared was installed to run the family’s real-estate empire. While still a joint law-M.B.A. student at NYU, he bought the New York Observer for $10 million and began landing in “Page Six” with girlfriend Ivanka Trump.

In reality, Jared’s public profile far exceeded his clout within the Kushner family. “Lets face it, Charlie is a strong-willed guy who is extremely focused on what he wants,” one top commercial broker who deals with the Kushners says. “Behind the scenes, it’s really Charles.”

With its stolid high-rises and families and fixed-income old people, Stuyvesant Town seemed an odd addition to the postgrad-playpen vision of the city.

By the fall of 2006, the Kushners wanted to grab a signature Manhattan property. After a failed bid to acquire 1211 Sixth Avenue for more than $1 billion, the Kushners set their sights on 666 Fifth Avenue. The problem was, the building wasn’t really for sale.

In October 2006, Jared placed a call to Rob. He had heard Tishman Speyer might be willing to sell a portion of their investment in 666 Fifth, but he wanted to buy the property outright. He bid $1.8 billion. On December 6, 2006, Jared and his team arrived at the offices of law firm Schulte Roth for the all-night negotiations. As dawn approached, Rob’s brokers directed Jared to wire a nonrefundable deposit of $100 million to Tishman Speyer’s account. When asked for the money, Jared stalled; he had only $50 million available and would need an extra day to transfer the full amount. “We’re going to get the money together,” Jared said.

Scott Latham, a Cushman & Wakefield broker representing Tishman Speyer, was furious. “This isn’t the way we do deals in New York!” he shot back. “We don’t need excuses that you’re trying to pull together money from five or six places.”

The tension mounted. If word leaked out that the deal was falling apart, it would damage Tishman Speyer’s chances with other bidders.

Calmly, Rob motioned to Jared, and the two left the room. In the hallway outside the conference room, Rob explained to Jared that the money needed to change hands now. “I’m not giving you 50 million dollars of my own money because I’m bullshitting you,” Jared told Rob. “You have to trust me.” Rob and Jared came to terms, and later that morning, a deal was signed.

“Rob and I are both lucky to have had great mentors,” says Jared. “Both of us would be content accomplishing a fraction of what our fathers have done.”

The sale of 666 Fifth Avenue kicked off a furious spate of sales for Tishman Speyer. Rob believed the commercial market was overheating. In the first half of 2007, Tishman Speyer sold $10 billion worth of properties, including some $3 billion in New York real estate alone. “We made a decision to sell most of our mature assets,” Rob says.

Rob’s ascension to co-CEO arrived in June 2008. In March, the MTA had awarded Tishman Speyer the rights to develop the 26-acre West Side rail yards, a billion-dollar deal. “My first job was working on what was then the new Madison Square Garden,” says Jerry. “You can imagine how I felt when Rob told me we were going to be the developers.”

But soon the talks with the MTA sputtered. Rob and his team reportedly sought to write a provision into the deal that would waive any lease payments until the land was rezoned, a process that could take several years; the MTA wanted money right away and wouldn’t budge. After an all-day meeting with Tishman Speyer’s management committee, Rob was prepared to sign the deal. But around 4:30, when he showed up at the office of Gary Dellaverson, the MTA’s chief financial officer, his heart seized. “It wasn’t the right deal for us,” Rob recalls. He asked Dellaverson to delay the meeting.

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