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Curbed's Whale of the Day: Michael Hirtenstein

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Boyish telecom mogul turned property whale Michael Hirtenstein may not be a household name, in fact, few outside of the NYC nightlife world have ever heard his name, but he has been behind more than a few high-end real estate deals. Since selling his start-up, Westcom Communications, for $270M in 2005, Hirtenstein has been linked to some of New York's most coveted buildings, and not always positively. In October of last year, Extell Development's Gary Barnett claimed that he had canceled Hirtenstein's contract on a high-floor unit at the unfinished blockbuster One 57 after the Hirt paid a construction worker to snap pictures from his unfinished sky-high flat. Hirtenstein told the Post, "You want me to spend $16 million without seeing it? ... All I was trying to do was be an informed, intelligent buyer. Apparently, that doesn't sit well with Mr. Barnett. That's not nice."

? Shortly after his telecom windfall came through, Hirtenstein dropped $15.7M on a sprawling penthouse at the then-new Time Warner Center, on Columbus Circle. High on the 76th floor, the 4,825-square-foot three-bedroom flat boasts one of the city's highest balconies. Apparently, Hirtenstein wasn't so enamored with the place personally, but he loved the profit potential. First, he rented it out to rap star Jay-Z for $40,000 a month, before flipping the apartment to Broadcast.com billionaire Todd Wagner for $27M. Wagner would eventually sell to Malaysian professional partier Taek Jho Low for $31M.

? Meanwhile, Hirtenstein was also pursuing a trophy property much closer to earth, at 23 Gramercy Park South, which he purchased in 2006 for $15M. Townhouses on that storied private park are rare enough, but this one had a doozy of a floorplan and an even bigger price tag when Hirtenstein went to sell. Listed for as high as $22M, the house received attention from plenty of celebrities—Sarah Jessica Parker, Matthew Broderick, and Anne Hathaway all had a look—but eventually sold to Columbian heir Andres Santo Domingo and his Vogue editor wife, Lauren, for $18.5M.

? Hirtenstein's real coup came at One York, a luxe Tribeca condo where he was said to have purchased a triplex combination for $35M. It turns out something went awry during the completion of the project. The Hirt sued the developer and ended up getting the same spread for a comparatively paltry $17.9M. What was so special about the place, well, for one, it has a sprawling outdoor space and a private, full-depth swimming pool.

· The New Kings of New York Nightlife [Forbes]
· He will Hirt you [NY Post]
· Jay-Z's Old Time Warner Rental About to Sell for $31 Million [Curbed NY]
· Not Ready for Adult Swim at One York's Ultimate Bachelor Pad [Curbed NY]
· All Whale Week 2013 posts [Curbed National]