When he bought those buildings from Equity Office Properties, he more than doubled the size of his real estate portfolio and used only $50 million of his own money to do so; he borrowed $7 billion to finance the rest of the purchase. Macklowe’s predicament marks the denouement of an unprecedented four-year period in which developers threw gobs of money at real estate as prices for office towers, especially in Manhattan, doubled and tripled almost as fast as sales could be recorded. Analysts, bankers and developers are not predicting the imminent collapse of the commercial real estate market, a reprise of the early 1990s, when property values dropped by half, vacancies soared and banks were crushed under the weight of soured real estate loans. Macklowe’s buildings on an apparent bet it might snare some great real estate on the cheap, bankers and real estate executives said. Macklowe about a deal for Macklowe Properties’ coveted Drake Hotel site, at Park Avenue and 56th Street, an executive involved in the talks said. Macklowe took a beating during a severe real estate recession, ultimately returning both the Riverbank West tower on 42nd Street and the Hotel Macklowe, now known as the Millennium Broadway Hotel, to the lenders. read more

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