David Wolkowsky, ‘Mr. Key West,’ dies at 99

Mr. Wolkowsky, seen here in 1994, told The Miami Herald in 1969 his goal was to “preserve the past by making it work for the present at a profit.”
Mr. Wolkowsky, seen here in 1994, told The Miami Herald in 1969 his goal was to “preserve the past by making it work for the present at a profit.”Timothy Greenfield-Sanders via New York Times

NEW YORK — David Wolkowsky, a visionary developer and preservationist who helped transform Key West, Fla., from a roistering former Navy town into a bohemian haven and a tourist destination, died there on Sunday. He was 99.

His death, at Lower Keys Medical Center in Key West, was confirmed by photographer Timothy Greenfield-Sanders, a nephew.

Mr. Wolkowsky was known locally as “Mr. Key West” for his role as a catalyst in the island’s revival. In recasting it as not only a vacation haven but also an artists’ colony, he befriended literary figures like Ernest Hemingway, Gore Vidal, and Judy Blume and rented his bamboo-topped two-bedroom trailer to Truman Capote, who wrote his unfinished final novel, “Unanswered Prayers,” there.


Jimmy Buffett got some of his first gigs playing for drinks in the Chart Room bar at Mr. Wolkowsky’s waterfront Pier House hotel, where he also featured reggae star Bob Marley.

By 1993, Islands magazine credited Mr. Wolkowsky, a native of the island, with “almost single-handedly converting Key West into America’s most distinctive tropical resort.”

He bought and restored the island’s original cigar factory and the Cuban ferry docks next to Mallory Square; helped rescue Captain Tony’s and Sloppy Joe’s, saloons of Hemingway fame; revitalized the old shops along Pirate’s Alley; and transformed the steamship office into Tony’s Fish Market.

Mr. Wolkowsky’s goal was to “preserve the past by making it work for the present at a profit,” he told The Miami Herald in 1969.

He hired architect Yiannis B. Antoniadis to design waterfront accommodations around Tony’s restaurant, which he named the Pier House in 1968 and which Renee d’Harnoncourt, a former director of the Museum of Modern Art, described as the “most unusual motel design in America.”

In 1974, Mr. Wolkowsky bought Ballast Key, an uninhabited 24-acre outcropping eight miles off Key West, for $160,000 and there built the southernmost private home in the contiguous (more or less) United States.


In August, the Monroe County Commission voted to rename the island David Wolkowsky Key after he died.

David William Wolkowsky was born on Aug. 25, 1919, a grandson of Jewish immigrants from Russia who had moved from New York to Jacksonville, Fla., and then to Key West, the southernmost Florida key, in the late 1880s. There they opened a men’s clothing store on bustling Duval Street.

His father, Isaac, ran the family store. His mother, Freda (Yubas) Wolkowsky, was a homemaker. When David was 4 and the local economy was failing, the family moved to Miami, where he grew up.

His closest immediate survivor is his sister, Ruth Greenfield.

Mr. Wolkowsky was on a pre-med track at the University of Pennsylvania in Philadelphia when he became interested in architecture and decided against medicine as a career.

“I wasn’t cut out to be a doctor; I was cut out to see a doctor,” he told Michael Adno in an article, “This Man Is an Island,” published this year in The Bitter Southerner, a digital magazine.

After inheriting property in Key West’s Old Town when his father died in 1962, Mr. Wolkowsky harbored visions of a life of leisure. But he was only in his 40s and failed miserably at retirement.

“I couldn’t bear to sit around and collect baseball cards,” he told The Herald in 2012. “If you’re not involved and enjoying what’s around you, you might as well get back in the book, like a leaf, and close it.”