David Wolkowsky driving the buggy at Ballast Key

David Wolkowsky, developer par exelence, is a true Key West treasure and easily the most interesting man in town. I met him a year ago, and I instantly recognized him for the mystical magical man that he is. Thanks to my own eclectic childhood, meeting everyone from royals to reg’lar folks, I know cool, and this guy is the real thing.

An invitation from David is a major highlight and might lead one to any of his splendid palaces about town; all filled with magnificient artwork and orchids in fat bunches fixed half way up a doric column brought back from the east, and everywhere there are photographs of himself with famous friends. And then there is his private island, Ballast Key, a few miles off the southernmost coast. In the interest of full disclosure, yes, I was invited out to Ballast Key, and I did discreetly plant a Serbian flag in the sugar white sand. The island getaway is a confection of airy beach house with unstoppable views and paths leading to sculptures for guests to stumble upon like a trail of candy. Yum.

The View from Ballast Key

When I met David Wolkowsky I was delightfully fascinated. He is chic and gentle with a nimble and witty mind, and I along with everyone who has ever met him, adore him. So when, recently, he phoned and proposed I write about his long-deceased friend author Patricia Highsmith I said yes absolutely, gladly. I was thrilled for the opportunity to give back after basking in so much of his hospitality.

Patricia Highsmith Poem

I plunged into the assignment and while I noted the wording of the poem is undeniably gorgeous the overall effect made me want to slit my wrists. According to Wikipedia Highsmith was prolific yet beset with the demon depression and no one had a nice word to say about her. While she was respected for her writing skills, her best known being The Talented Mr. Ripley quote after quote described her as “relentlessly ugly”. This was dispiriting but I was determined to fulfill this special request.

I phoned David, “Couple of questions,” I said, “First off, did Patricia write this about you?” Mercifully he said, “No! I have no idea why she picked that to send me. But she signed it so I had it framed.” About Highsmith he said, “I met Patricia in New York. I knew her fairly well and she was always very good company.” I was on the verge of revealing my miserable research thus far when I saw the light at the end of the tunnel and I slid in questions about his far more interesting self, garnering nuggets such as his memories, as a young child, of the excitement of riding the Flagler Railroad from Miami to the Keys. David Wolkowsky’s childhood was spent, “floating around between Key West and Miami”. The Wolkowsky family, having first moved to Key West in the late 1880s, owned properties in “old town” and in 1962 David decided to settle. By 1963 he was managing a brilliant deal to develop a waterfront property near Mallory Square. He is perhaps best known for building the Pier House Hotel, a resort where both Jimmy Buffett and Bob Marley started their careers in the hotel’s “Chart Room Bar”. Buffett credits Wolkowsky as the first to hire him.

For over half a century Wolkowsky has invested in what is often described as a drinking town with a fishing habit. With environmental and cultural sensitivity David Wolkowsky has saved, restored and built, bought and sold much of the local real estate. He is much loved for helping to preserve the look and feel of this unique port of call. He is a philanthropist quietly and steadily supporting the humanities on many levels. Everything from funding prizes for teachers to helping the homeless to investing in his artist friends. One of his favorite authors is P.G. Wodehouse, “But,” he says, “The only problem is the expectation of a ‘Jeeves’ which is never be found in real life.”

David Wolkowsky, Truman Capote and Tom McGuane

Locals vividly recount every cherished sighting, and they say that when they drive their boats past his island, they gasp and sigh at the perfectness of it all. But I watch tourists soaking up all the loveliness and I have to wonder if they know anything about my friend David, the man who intimately helped create this place they so enjoy. I think I need to push for an official David Wolkowsky Day.