Florida Keys

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

David Wolkowsky, whose vision for Key West helped transform it from an island in decline into a colorful tourist destination that draws artists and writers, died Sunday night at 99.

He had celebrated his birthday on Aug. 25 in true Wolkowsky style: a house full of free-spirited guests, clouds of white orchids, popping champagne corks and his sister, Ruth Greenfield of Miami, a classically trained concert pianist and civil rights pioneer, playing happy birthday on the grand piano as the crowd sang along. He presided from the white couch, dressed in linen, his trademark Panama hats stacked nearby. And instead of receiving gifts, he gave them: a black pearl necklace in a jeweler’s box for each of the several dozen women who attended.

He was known as Mr. Key West for the way he shaped the city’s downtown since the 1960s, renovating, restoring and even relocating the weathered buildings that created a quaint downtown for tourists and a haven for artists.

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David Wolkowsky in Key West in photo taken for L’Uomo Vogue in 1994. Timothy Greenfield-Sanders

Born in Key West in 1919 — his grandfather had opened a general store there in the 1880s — Wolkowsky and his family moved to Miami when he was a child. He attended the University of Pennsylvania, then built a career restoring buildings in Philadelphia. He returned to Key West at 42, when his father died. He had planned to retire, but once he saw Key West’s buildings and its relatively blank canvas, he saw a world of possibilities.

Wolkowsky opened the Pier House hotel in 1968, which began to draw visitors from around the country, including author Truman Capote, who noted its air of “elegant inefficiency.” Part developer and part preservationist, Wolkowsky renovated more properties than he could remember, including Ernest Hemingway’s original watering hole, Capt. Tony’s Saloon — which Wolkowsky and his sisters inherited from their father — and the Kress building, an old dime store in the heart of Key West. It’s now home to both Jimmy Buffett’s Margaritaville Cafe and a rooftop penthouse Wolkowsky built for himself. Much of Duval Street and Mallory Square, two major tourist areas, were originally Wolkowsky creations.

In a 2012 Miami Herald interview, Wolkowsky summed up his drive to create: “I couldn’t bear to sit around and collect baseball cards,” he said. “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.”

Every year, during the Key West Literary Seminar in January, he threw a cocktail party in honor of one of the best-known authors. It was always held in the penthouse, offering a panoramic view as the sun set.

David Wolkowsky on Ballast Key in photo taken for L’Uomo Vogue in 1994. Timothy Greenfield-Sanders

A friend of writers including Capote, Tennessee Williams and, in recent years, Judy Blume, Wolkowsky remained an avid reader throughout his life, combing the Sunday book sections for new books he wanted to read. In later years, he would ask his driver to take to him to the Books & Books store in Key West, where Blume is the bookseller, to pick up his latest acquisitions.

He was also the owner of the southernmost private home in the United States on Ballast Key, a scrubby rock outcropping in the Key West National Wildlife Refuge that he bought in the 1970s. He built a modern stilt home on the island, 8 1/2 miles from Key West. Construction of the art-filled home inspired by a lighthouse took years and required both a barge and a desalinization plant.

Last month, the Monroe County Commission voted to rename the island David Wolkowsky Key after his death, although the ultimate decision rests with the U.S. Board on Geographic Names.

Wolkowsky watched the vote from a wheelchair in the audience, telling reporters in his dry manner, “I wanted to see the commission, en masse.”

In March, he participated in a march to protest gun violence, rolling down the street in the passenger seat of one of his vintage cars, a cream-colored Excalibur, while others in the car held a sign saying, ”Never Again.”

He was known for his taste that mixed high and low. In the penthouse, an expensive Art Deco-style Aubusson rug lay on a floor of polished plywood. On Ballast Key, he happily served guests turkey hot dogs and chips — with a chocolate soufflé for desert and a priceless view in every direction.

He hosted luminaries at his various homes in Key West for decades. But the real prize was an invitation to Ballast Key. British Prime Minister Edward Heath, Leonard Bernstein and musician Buffett — who performed at the Pier House when he was a young singer — all got the nod.

David Wolkowsky, 98, at the Monroe County Commission meeting on Aug. 15, 2018, when the commission voted to name Ballast Key after him. Gwen Filosa FLKeysNews.com

In recent years, he had been on a drive to promote little-known Tennessee Williams paintings that he owned. The paintings, depicting love and loss, are currently exhibited at the Jewish Museum of Florida-FIU in Miami Beach.

Williams painted one portrait of Wolkowsky. It’s inscribed on the back with the words: “It’s the eyes.”

Wolkowsky died at the Lower Keys Medical Center in Key West. No arrangements have been announced.