Real Estate Super Bowl! Who Will Vie For GM Building?

Not so long ago, Harry Macklowe was sitting pretty, pulling off one of the largest-ever buys of a commercial portfolio,

Not so long ago, Harry Macklowe was sitting pretty, pulling off one of the largest-ever buys of a commercial portfolio, adding it to a trophy case of holdings that included arguably the city’s most desired office property, the General Motors Building at 767 Fifth Avenue.

But now, with weeks until billions in debt are due and CB Richard Ellis marketing the GM Building for a possible sale, the once mighty house of Macklowe seems ever closer to tumbling down in a high-profile collapse. With his predicament well known in the industry, the vultures are surely circling overhead, with the biggest players in New York real estate watching closely for the opportunity to snatch up the glimmering white 50-story trophy on the southeast corner of Central Park.

Of course, people familiar with Mr. Macklowe’s situation say a sale is far from certain. Depending on offers and the terms he is able to negotiate with his lenders, the action that results could be an unsexy recapitalization of the property, if anything at all.

But for now, the tantalizing possibility remains that the GM Building could indeed be sold, a deal that would easily be the largest single building sale ever, with many in the industry saying $3.5 billion could be merely a starting point for bidding (almost double the current building-sale record of $1.8 billion, which belongs to 666 Fifth Avenue).

So if the GM Building does go up for bid, who could line up in the battle royal for the chance to buy?

Will it be Sheldon Solow, the 79-year-old determined, extremely litigious owner and developer of the prized 9 West 57th Street? Mr. Solow bid for the GM Building in 2003 and, in a still active lawsuit, claims he was the high bidder and rightful winner of the property.

Or perhaps Larry Silverstein, the powerful downtown developer? Mr. Silverstein, who is said to laud the trophy that is the GM Building, is armed with the backing of CalSTRS, a California teachers’ retirement fund that went in with him on the $1 billion buy of 1177 Avenue of the Americas late last year. He’s likely used up much of the $2 billion CalSTRS committed to him, though his deal with the pension fund leaves the door open for future installments.

Then maybe there’s Steven Roth, chairman and CEO of Vornado Realty Trust—the aggressive, forceful owner of the city’s most active real estate investment trusts. Mr. Roth has a bit of history of losing out to Mr. Macklowe, and perhaps he’s anxious to plant his flag in the ground of his rival’s faltering empire. He bid on the building himself in 2003, losing out to Mr. Macklowe. Then, last year, Mr. Macklowe whisked away the Equity Office portfolio that Mr. Roth was trying to wrest from tycoon Sam Zell.

And how about Jerry Speyer, the longtime CEO of titan Tishman Speyer? Mr. Speyer has a history of buying really, really expensive buildings and complexes—the MetLife Building, Rockefeller Center, Stuyvesant Town, the list goes on.

Or will the onetime part owner of the GM Building, Donald Trump, make another go? Mr. Trump was forced to sell his stake in the building in 2003 when partner Conseco Inc. went bankrupt. However, he told The Observer a bid from him is unlikely. “I don’t think I’d have any interest,” Mr. Trump said Monday. The building is an absolute “iconic” tower, he said, mostly on account of location.

Of course, Mr. Trump added, “57th and Fifth would be an even better location—that’s where Trump Tower is.”

Real Estate Super Bowl! Who Will Vie For GM Building?