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Who

The founder and chairman emeritus of Macklowe Properties, Harry Macklowe has witnessed his fortunes rise and fall with the swinging pendulum of the real estate market over the past two decades. Now in the twilight of his career, he officially handed over control of the company to his son, Billy Macklowe, in June 2008.

Backstory

After dropping out of college three times—his would-be alma maters include the University of Alabama, NYU, and the School of Visual Arts—Macklowe got started in real estate in 1960 as a leasing broker working for Julian Studley. Macklowe soon branched out on his own, making a name for himself in the '70s selling property in the flower district in the West 20s. He'd already moved into small-time development and acquired a reputation as a fearsome competitor when, in the course of a single night in 1985, he became one of the most notorious figures in the city: In an attempt to beat a deadline for tearing down welfare hotels, Macklowe demolished two such properties just off Times Square without warning, not even bothering to fill out the necessary paperwork or turn off the gas first. A massive public outcry followed (Ed Koch returned his campaign contribution) and Macklowe agreed to pay the city over $2 million in compensation before building the Hotel Macklowe on the site.

Macklowe followed up over the following years with the Metropolitan Tower on West 57th Street, one of the first big luxury residential towers in Midtown. (Famously, Macklowe promoted it as a 78-story condo on account of its high ceilings even though it only had 65 floors.) During the real estate bust of the early '90s, Macklowe fell on hard times and was forced to sell off the Hotel Macklowe along with a handful of other properties. He rebounded in the early '00s only to suffer yet another downfall in the wake of the subprime mortgage crisis.

Of note

Macklowe cemented his return to the top tier of commercial real estate in 2003 when he paid $1.4 billion for the General Motors Building, which was the largest amount ever paid for a single New York commercial building at the time. Despite a good deal of sniping at the time that he'd overpaid, Macklowe's gamble seemed especially prescient a couple of years later when the building was valued at almost double what he paid for it. With the real estate market heating up, Macklowe soon set off on a ferocious buying spree: In February 2007, Macklowe spent a record-breaking $7.25 billion for eight Midtown office buildings owned by Steve Schwarzman's Blackstone Group. (Schwarzman had acquired the buildings in December 2006 as part of his buyout of Sam Zell's Equity Office Properties.) More than 6.5 million square feet in total, the purchase included Worldwide Plaza, 850 Third Avenue, the Park Avenue Tower, and 1540 Broadway.

Macklowe's return to the top of the property pile was short-lived. The credit crisis wiped out the generous debt financing that had once been available and with interest rates rising, Macklowe was forced to come up with billions to repay debtors such as Deutsche Bank and the Wesley Edens and Peter Briger-led Fortress Investment Group. When he had difficulty coming up with the cash in February of 2008, he was forced to relinquish control of the buildings he'd purchased from Blackstone a year earlier; in May 2008, he was forced to sell his crown jewel, the GM building, to a consortium of investors including Mort Zuckerman's Boston Properties, Goldman Sachs and the governments of Qatar and Kuwait for $2.9 billion. As part of the deal, Macklowe also parted ways with five other Midtown office buildings, worth more than $1 billion. Macklowe's company continues to control several commercial properties; the firm has also held on to several residential properties, including Rivertower, the building he inhabits.

Keeping score

Forbes placed Macklowe's net worth at $2.0 billion in 2007 when they named him to the Forbes 400 list. Given the events of the past year, Harry won't have the pleasure of seeing his name in print in 2008. (He's believed to be worth $500 million these days.) Fortunately, de-stressing massages will be soon available at Miraval, the massive Upper East Side spa that Macklowe has invested in along with ex-AOL CEO Steve Case.

Family ties

Harry is now chairman emeritus of Macklowe Properties. His son, Billy Macklowe, is president and the firm's chairman as of June 2008. (Father and son have clashed over the family's real estate misadventures in recent years, and Billy was instrumental in the deal to sell off the GM building in 2008.) His son-in-law is real estate mogul Kent Swig.

Personal

Harry is married to Linda Macklowe, a Guggenheim trustee. They have two kids: In addition to Billy, there's daughter Elizabeth, who's married to Macklowe's onetime protégé, Kent Swig. Harry and Linda reside in a duplex in the family-owned Rivertower on the East Side; they also own one of the most expensive apartments in the city, having paid $60 million for an apartment in the Plaza in 2007. (The 13,000-square foot pad was designed by Charles Gwathmey.) The Macklowes also own a duplex in the RiverTower on the East Side as well as an estate in East Hampton.

Grudge

In 1997, Macklowe and Martha Stewart engaged in a much-publicized legal spat over the landscaping on their adjacent estates in East Hampton. The feud began when Stewart removed a number of trees and shrubbery that she alleged Macklowe had illegally planted on the land connecting their properties. It quickly deteriorated into a flurry of mutual lawsuits—and it was one court battle that Martha actually won.

Off hours

A competitive sailor, Macklowe has a 112-foot racing sloop named Unfurled.