In New York, where Mr. Sitt owns 11 waterfront acres of Coney Island, he is having a hard time proving the point. (His plans for hotels and condominiums have failed to win city approval, and the future of the area is in doubt.) But in Chicago, Mr. Sitt has restored the Palmer House Hilton, a huge hotel he bought in 2005. The hotel had been a dowager for so long, according to Mr. Sitt, that Chicagoans were skeptical about his promises to bring it back to life. But the renovation has not only improved the hotel, it has also helped revive a once-downtrodden section of the Loop.

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