Not so long ago, Harry Macklowe was perhaps best known for his long-running feud with billionaire homemaker Martha Stewart.

Throughout the mid-1990s, the two East Hampton, New York, neighbors engaged in a thorny battle over the size of Macklowe’s hedges, his lighting fixtures, and a fence that Stewart complained blocked her view of a pond. The feud cost hundreds of thousands of dollars in legal fees and became juicy tabloid fodder when Macklowe’s 23-year-old handyman accused Stewart of pinning him against a gate control box with her Chevy Suburban.

In January, the elder Macklowe, with his bushy, black eyebrows and immaculately cut suits, surprised competitors when he agreed to buy Equity Office Properties’ New York City buildings from the Blackstone Group for $7 billion. Before that, Macklowe won renown for his record-setting purchase of the famed General Motors Building, home to F.A.O. Schwartz, which is perhaps the most-sought-after address for today’s Masters of the Universe. It’s also home to the highest office-rental rates in the city, with space on the penthouse floor going for as much as $175 per square foot. In February 2007, Macklowe Properties also bought Worldwide Plaza for $1.73 billion, the second-most expensive sale price of a single building in U.S. history. The Macklowes’ long list of tenants at their various properties include Icahn Partners, Perry Capital, Thomas H. Lee Partners, and SAC Capital Advisors, the $12 billion hedge fund behemoth headed by Steve Cohen.

Like another onetime owner of the G.M. Building—Donald Trump—Macklowe soared high in the 1980s, then faced some setbacks during the recession of the 1990s and is now building big. By riding the current bull market, Macklowe has leveraged a midlevel real estate profile into an unparalleled collection of properties that places him near the top of the heap. “He’s had a very interesting career. He’s been very successful, then very unsuccessful, and then come back and been very successful [again],” says rival New York City real estate developer Douglas Durst.

THE FOUNDATION

Neither Macklowe nor his son Billy would speak on the record for this article. But the outlines of Harry Macklowe’s résumé are well known. The son of a garment executive, he started off in the real estate industry’s version of the mailroom in 1960 as just another anonymous broker at Julian Studley Inc.

By the mid-1960s, he was doing deals of his own, trading up to increasingly ambitious residential projects throughout the 1970s. Michael Cohen, chairman of GVA Williams, one of New York’s largest commercial-property management companies, pegs Harry Macklowe’s coming out party as a commercial developer to the early 1980s, when he acquired an old nine-story warehouse, converted it into office space, and signed New York Telephone to a 10-year, $50 million lease. Then he built Grand Central Tower, on 45th Street between Lexington and Third Avenues.

Macklowe defied common wisdom by building on a side street in an area that was questionable at the time. But to the surprise of many real estate industry insiders, he inked a deal with what was then Hanover Trust to take half the floors.