SROs left a stench about him. Subsequent headlines almost always conjured up a ruthless, sinister profiteer. The story lines were variations on a theme: He bought buildings; he lost them. He fought with tenants, with everyone. He defaulted on loans. He played hardball. Some of the headlines: In 1995 he was embroiled in a long-running border dispute in East Hampton with neighbor Martha Stewart over a row of trees he put up – and she took down. In 1997, as he was clearing a building site at Second Avenue and 53rd Street, he evicted 13 rent-controlled tenants, including an 82-year-old blind man, Carl Steindler, who compared the eviction to a death sentence. Later that year, bricks fell onto the sidewalk from a building Macklowe had bought on Madison Avenue. And, again, he was lucky no one got killed.
It seemed he couldn't outrun his origins. Macklowe was an outsider, a hustling striver in a world of very rich men. The son of a textile converter, he used leverage – borrowed money – to buy properties, while many of those around him – the children or grandchildren of rich families with names like Rudin, Durst, and LeFrak – “viewed leverage, at least on a grand scale, as a last resort.” But what was Macklowe, a college dropout from upstate New York, to do? He wasn't rich and he was in a hurry. “I was impatient,” he says of his early days in the business. Leverage was the only way he could play in New York City's rocketing real estate market.
By the late 1990s, his net worth was around $100 million. But he wanted much more. “I just.. love it; it's a challenge, and I love being the designer. I love being the architect. I love being able to execute my vision, and I think my vision – this is obnoxious – I just think my level of taste is better than most architects’. I think I have my finger on what it is that I want to do, and the actor in me, that little bit of bravado, all of that shit which just bubbles up, gives me a lot of gratification, and kinda drives me to it. So I could talk passionately about how this [building at 610 Broadway] was a car wash, and I bought it from a Russian Jew. I did this, and I did that. But what I'm most proud of is the graceful lines of that building, the glass elevator there. Nobody has a glass elevator to the street. This is hot shit,” he said.
A friend of the Macklowe's put it this way: “There's a German expression, Profilneurose; it means literally ‘fear of invisibility.’ That's what Harry had. He wanted to be recognized for the attributes he saw so clearly in himself.”
In June 2003, Harry the scrapper wasn't about to give up the idea of owning the GM Building just because he might have been the poorest man in the bidding. He had said he was going to buy the GM Building, and he would. He believed he had a plan – a vision – for how to make the building more profitable.
“A very clever entrepreneur who sees something there that somebody else doesn't see.. has the advantage,” he says. “I perceived that to be the best piece of real estate in the city;.. it was being sorely neglected, there was room to grow the rent, there was room to change the building.”
In a spin that only the very bold or very delusional can manage, Macklowe saw his lack of funding as another advantage: “I didn't have to sit with a loan committee. I didn't have to sit with an investment committee… I could be much more nimble than a larger company… I could feint, weave, adapt.”
“Why do I do what I do?” he asked rhetorically one sunny afternoon in his office. “I do it for the money, the drama. And the satisfaction of being right.”
Chapter 2
Alpha Males
You need people who are loyal to you if you are an entrepreneur.
It was time for Harry Macklowe to call the consiglieri —the two advisers he had relied on more than anyone else since the mid-1990s. Both men were called “Rob.”
Robert “Rob” Sorin was a partner at the Fried, Frank, Harris, Shriver & Jacobson law firm. He was dark-haired, bespectacled, and polished. He and Macklowe had begun working together when Sorin was a lawyer at the real estate law firm of Robinson, Silverman, Pearce, Aronsohn, and Berman. Macklowe followed him to the broader, more international firm of Fried Frank in 1997. That was a typical Macklowe move. He was fiercely loyal to people, not institutions.
And it was easy to be loyal to someone so talented and useful: Sorin was a rising star. A graduate of Georgetown University, he had made his mark on the New York City market by executing the sale of the Metropolitan Transportation Authority (MTA)’s New York Coliseum – a 3.43-acre site to the southwest of Central Park – for $337 million. He had accomplished this after a decade of volatile negotiations among the city, the MTA, and Mortimer “Mort” Zuckerman – whose $455 million proposal to develop the site collapsed in 1994.
Macklowe appreciated Sorin's quiet, careful style. Other lawyers, bankers, and brokers knew him, trusted him, and liked dealing with him. He diplomatically described the extreme peaks and troughs of Macklowe's professional life as, simply “interesting.” It also helped that Sorin, aged 45 (in 2003) was younger than Harry but older than his son, William “Billy,” then 35, who had started working for his father soon after graduating from New York University.
When Macklowe told Sorin he was planning to buy the GM Building, Sorin wasn't surprised. He'd have been surprised by anything less audacious. “When he latches his jaws onto something, it's very hard for him to let go. When [the GM Building] became a real opportunity.. he was very, very focused on it,” Sorin recalled.
Sorin sensed Macklowe had been plotting his move on the tower for months. Earlier in the year, Macklowe had asked Sorin to represent him on a deal that had seemed unusual. Macklowe said he would buy the land under the old St. Moritz Hotel on Central Park South (now the Ritz-Carlton). It was a small deal – $125 million – with no opportunity for development. “It wasn't a typical Harry acquisition,” Sorin recalls. “There wasn't a lot of creative opportunity to it.”
Macklowe told Sorin he knew the deal was “flawed.. but” – and this was a crucial “but” – Eastdil was the selling agent. Eastdil, it was known, would, most likely, be the selling agent for the GM Building. Eastdil would want to see a track record from Macklowe before it would take him seriously as a buyer of something as monumental as the GM Building.
“I don't give a shit – let's just close the deal,” Macklowe told Sorin. He explained, “I wanted to have a reputation of being a closer, being honorable, and having done a deal with these guys.”
Sorin understood. He drafted the paperwork and negotiated the deal.
The counterpoint to Sorin's white-shoe persona was a broker named Robert “Rob” Horowitz. The “other Rob” in Harry's stable had played a vital role in every one of Macklowe's deals since 1997, amounting to over $15 billion in transactions.
“Rob,” Macklowe said to the broker, a slight man with shoulder-length dark hair that curls at the ends, “we're buying the GM Building.” There was a brief pause as Horowitz leaned back in his chair. “We need some money.”
Cooper-Horowitz, the brokerage started by Horowitz's father, Barry, did not believe in wasting its fees on office rent. The firm had occupied smoke-filled rooms with aging black vinyl sofas in the Grand Central Terminal station area for 50 years. “We don't bring our clients to meetings here ever,” Rob Horowitz chirps through the gloom and stench. “I don't want to spend a nickel I don't have to.”
“Nobody thought that Harry was going to be the winning bidder – nobody,” says Horowitz. “Because most people thought that the amount of equity that would be required would be too large for just an individual to buy. That's why everybody thought the building was going to be traded to Vornado [a vast public real estate
