Key West Wrangle

It's a sticky midweek morning in Mallory Square, Key West's tourist mecca. A mammoth cruise ship disgorges passengers eager to gawk at Ernest Hemingway's six-toed cats and guzzle drinks at Jimmy Buffett's Margaritaville. The tourists are pink from the sun and dressed in carefully ironed white shorts and T-shirts that sport insipid or crude slogans like "Life Is Good" and "I Pee in Pools." A gaggle of fat-bottomed older ladies coos over an aggressive and handsome rooster, while a guy rides through the plaza on a purple bike.

Purple Bike Guy bears a healthy resemblance to the town's most famous resident, writer Papa Hemingway — if Hemingway had been missing a front tooth. White beard? Check. Kind, crinkly eyes laced with sadness? Check. A ruddy face from decades of hard drinking? Check.

He stops to rest on a bench and lights up a smoke. His name, he says, is Tony Beach and he is 62 years old. Tony claims to have a title — "The Mayor of Smathers Beach" — because he hangs out there just about every day. For more nights than he can remember, he slept in the mangroves nearby. Tony has been in Key West for 20 years and has been homeless for the majority of that time. "I lived over there for a year," Tony says, pointing with the cigarette to his right, toward a spit of land just 2000 feet off Mallory Square.

The spoil island has an official name — Wisteria — but Tony and almost all the other locals call it Christmas Tree Island because of the once-thick stand of furry Australian pines that was mostly whipsawed by Hurricane Wilma in 2005. It's a flat, undeveloped plateau that for three decades has been an outlaw homeless community and party spot of legendary proportion.

Like almost all the other longtime Key West characters, Tony has endless stories about Christmas Tree Island, where he camped out in a makeshift lean-to made of two-by-fours, plywood, and tree branches. A few dozen people lived there at the time. Most of Tony's tales involve Jack Daniel's, weed, and, inexplicably, singing Fifties doo-wop tunes in the moonlight. Despite everything bad that's happened in Tony's life — Vietnam, homelessness, more than a few arrests — he still has the voice of a 25-year-old.

"Try the impossible, try to understand," Tony croons, his tone as smooth as the ocean breeze floating across Mallory Square. "The way I feel about youuuuuuuu."

He chuckles when he remembers the guys who lived and sang with him among the island's pine trees. "They're all dead now," Tony says. He pulls out a cigarette and lights it with the nub of the one in his mouth. "A dude named Gangrene. Moldy Mike. I never knew their real names. They died of cancer, heart attacks, hard living. I remember one dude on the island; he got the wrong dope, I guess. We found him dead in his lean-to. His dog was next to him, protecting him."

Lately Tony has been forced to relive those memories, because on November 6, Key West voters will cast ballots on a measure to essentially decide the island's future. A group led by an aggressive Key West developer and a quiet Miami lawyer hopes to develop 168 condos, transforming Christmas Tree's 21 acres into something akin to the brightly hued, multimillion-dollar homes on Sunset Key, another spoil island just a few hundred yards away.

The runup to the vote has been infused with secrecy and impropriety — perhaps to be expected in a place where federal officials once deemed the city's police department a racketeering enterprise. After enduring 25 years of rapid luxury growth and a squeezed-out middle class, the island's residents are incensed over any development on Christmas Tree Island. "That's the last nice piece of Key West," Tony says in a raspy voice. "We should put a park there. Let people enjoy Key West the way it used to be."

Despite Key West's modern-day tourist draw, the city's best days are behind it. In the 1800s, it was the most populous and richest place in Florida, drawing shipwreck salvage crews, fishermen, Bahamians, and Cubans to the southernmost point in the United States. And it was a natural stopover for the cigar trade between Tampa and Havana. In the mid-1800s, Fort Zachary Taylor and nearby Fort Jefferson served as outposts for the Civil War.

Wisteria Island sprung up from all of this prosperity. In 1890, the U.S. Navy began dredging Key West Harbor. The coral rock and sand pulled from the ocean floor was piled up in two places; the navy called one site Tank Island (it later was renamed Sunset Key) and the other Wisteria Island, which got its moniker from a U.S. steamer that burned and sank while moored there.

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Tamara Lush