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His grandfather, Abraham Wolkowsky, moved to Key West in the late 1880s and established a fine clothing store on Duval Street. The late Edna Wolkowsky was his sister. His other sister, Dr. Ruth W. Greenfield, is the prominent Miami musician and social activist. His nephew is the photographer and filmmaker Timothy Greenfield-Sanders.
Restoration and rejuventation
David Wolkowsky grew up in Key West and Miami and received his degree from the University of Pennsylvania. After college, he began to restore buildings in the inner city of Philadelphia. He is credited with starting the rejuvenation of Society Hill and Rittenhouse Square in that city.
Wolkowsky visited Key West in late 1962, after the death of his father, Isaac Wolkowsky. The family had a few properties in "old town" Key West and Wolkowsky decided to "retire" to Key West at the age of 40. Unable to sit still, he rescued a condemned bar on family land on Greene Street, which was the original home of "Sloppy Joe's" of Hemingway fame. From there he developed property on lower Duval and Front Streets including "Pirate's Alley" and the "Original Cigar Factory". In 1963, Wolkowsky accomplished a major real estate coup by purchasing, for $106,000, the old Cuban Ferry Dock, choice waterfront property near Mallory Square.
Wolkowsky lifted the 1890 Porter Steamship office off its foundation and moved it 300 feet (91 m) out, setting it on pilings in 40 feet (12 m) of water. He transformed the Steamship office into "Tony's Fish Market", a restaurant and cocktail lounge where guests could watch shrimp boats in the channel on their way into port. He is credited with putting Key West on the road to being a major tourist destination.
In 1967 Wolkowsky hired architect Yiannis B. Antonidis to help design a motel around the restaurant, with 50 unique rooms, to which 50 more rooms that faced the ocean were quickly added. The completed structure was christened "Pier House Resort Motel". Both Jimmy Buffett and Bob Marley started their careers in the hotel's funky "Chart Room Bar". Buffett credits Wolkowsky as the first to hire him.
The Pier House became a magnet for celebrities and media types, mostly because of Wolkowsky's unique personality and laissez-faire attitude. When writer Truman Capote arrived at the hotel to spend the winter he asked Wolkowsky to show him the best rooms. After viewing several choice units, Wolkowsky invited Capote over for a drink, to his residence of the moment, a 45-foot (14 m), two-bedroom, double-wide trailer, covered in bamboo and parked 10 feet (3.0 m) from the hotel's waterfront. Capote begged Wolkowsky to rent him the trailer. Wolkowsky finally agreed and moved into a suite of rooms, in his own hotel, for the winter, to accommodate the writer. Capote's "Answered Prayers" were written in Wolkowsky's waterfront trailer. Discarded handwritten pages were often given to Wolkowsky by Capote in gratitude for allowing him to write in the trailer. Years later, the papers were stolen from Wolkowsky's penthouse apartment, high atop Key West's former Kress five and dime. Wolkowsky had restored the building, renting out the ground floor to department store "Fast Buck Freddies" and the upper floors to the Key West Parole Department. He is quoted as saying, "I never felt safer than when I lived above the Parole Board. The Capote papers were stolen by someone I know, not by a parolee".
While building the Pier House, Wolkowsky bought Ballast Key, an uninhabited, private island, 8 miles (13 km) off Key West. He built a large house and guest house on the island and entertained many of his writer friends there, including Tennessee Williams and Capote. He is known for serving hot dogs, white wine and potato chips to guests including British Prime Minister Edward Heath, various Rockefellers, Mellons and Vanderbilts. During construction of the island Wolkowsky sent his private barge out to the island loaded with building supplies as well as with chocolate pudding and souffles, from The Pier House kitchens, for his laborers.
Wolkowsky continued to restore dozens of homes around Key West, as well as building the original "Reach Resort" across town. He could always be spotted, wearing several pairs of sunglasses on his head and some hanging from his neck, while driving around town in either his golf cart or his 1926 Rolls-Royce.
In 2000, Wolkowsky created a Teacher Merit Awards fund, which gives $5,000 to each of nine Key West teachers as well as a $25,000 award to a single teacher each year. About teachers in Key West, Wolkowsky was quoted in the Key West Citizen saying, "They have to be protected and nurtured".
In the mid-1990s, a street adjoining the Key West Historical Society was named "David Wolkowsky Street" in his honor.
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