Key West Wrangle

Sides square off over Christmas Tree Island

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.

This summer the owners of Christmas Tree Island posted No Trespassing signs on the property to keep locals away
Michael Torbisco
This summer the owners of Christmas Tree Island posted No Trespassing signs on the property to keep locals away
Jimmy Buffett popularized the beach bum lifestyle in Key West
AP Wide World
Jimmy Buffett popularized the beach bum lifestyle in Key West
Bruce Ritson, a 30-year Key West resident, is trying to stop the development of Christmas Tree Island
Tamara Lush
Bruce Ritson, a 30-year Key West resident, is trying to stop the development of Christmas Tree Island

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.

The dredging project lasted well into the Twenties as more and more people poured into Key West thanks to Henry Flagler's overseas railroad. In the Thirties, just a few years before Hemingway bought his house a half-mile from Mallory Square, a Key West state representative named Bernie Papy bought Wisteria Island for $3000 — and promptly turned it into a shark camp, where workers brought their haul, made leather from the predators' skin, and then shipped the remains to China, where they were used to make medicine.

In 1956, Papy sold his island to a group called the Wisteria Corporation, which wanted to erect 60 homes, a golf course, and a yacht club. Although board members hired architectural consultants who had worked on Lincoln Center in New York, they sold it in 1967 without hammering a nail. The new owner, local land baron Benjamin Bernstein, also had the development itch; he had already built many homes, trailer parks, and commercial buildings on Stock Island, just east of Key West. In 1973, Bernstein and his family bought 150 acres of bay bottom surrounding Christmas Tree Island. But then Bernstein died in 1974, and his wife and two adult sons left the island untouched.

The first squatters probably arrived on Wisteria/Christmas Tree Island in the Sixties or early Seventies. It was a time when many young hippies headed south, and Key West became an affordable, tropical, counterculture retreat. One of them was Paul LaBombard, who hitchhiked there from Massachusetts in 1971 when he was 18 years old. He slept on a porch and then pitched a tent on Wisteria Island for a winter before drifting to India, where he changed his name, studied Buddhism, and donned a turban. Upon returning to the United States, he bought a 10-unit apartment building in Portland, Maine. By 1987, he was calling himself Pritam Singh and had amassed enough wealth with his developments to buy Key West's Truman Annex and embark on a $250 million project, which included the Key West Golf Club.

Like Singh, Jimmy Buffett arrived in Key West in the early Seventies. He came with fellow guitar picker Jerry Jeff Walker in an old Packard. It's unclear whether he stayed on Wisteria Island — Buffett refuses to give interviews to anyone these days — but he lived aboard more than one sailboat, so it's likely he cracked open a beer on its shores. He cut his third album, A White Sport Coat and a Pink Crustacean, while living in Key West in 1973. Four years later, he recorded his most famous song, "Margaritaville," which became an anthem for hard drinking and island living:

I blew out my flip-flop,

Stepped on a pop-top,

Cut my heel, had to cruise on back home.

But there's booze in the blender,

And soon it will render

That frozen concoction that helps me hang on.

Tony Beach arrived in Key West around 1987 and claims to have worked a day-labor landscaping gig at a house Buffett owned on the island. "It was a really hot day," Tony snorts. "We went to the door and asked old Jimmy for some ice water. He said the hose is over there, and pointed ... like we were dogs.

"Jimmy Buffett is a bimbo. He's nothing but a fart in an iron lung."

As a real estate boom took hold in the Eighties, people like Tony were squeezed, so they headed to Christmas Tree Island, which was then a crazy place. There were dozens of people living there, most of them in small lean-tos. Walking paths crisscrossed the tall brush, and fire pits pockmarked the beach. A woman named Delilah lived aboard a sailboat anchored offshore with her husband and two children for more than 10 years. She called the island "a back yard for boaters."

"One year we all went ashore for Thanksgiving and we barbecued a turkey," she recalls.

Mark Rossi, the owner of Durty Harry's and Rick's — two popular Duval Street bars — began hosting end-of-the-tourist-season parties on Christmas Tree in 1985. Live reggae bands played on a barge offshore, and Rossi provided food and lots of booze. "It was always an island-party theme," says Rossi.

In the early Nineties, Key West commissioners got tired of the homeless and voted to close public beaches at 11:00 p.m. But the measure backfired when a Monroe County judge rejected the measure as unconstitutional, and the decision was trumpeted around the nation as a sign of the city's insensitivity — and very non-Jimmy Buffett attitude.

Christmas Tree Island remained a freeloader haven throughout the Nineties. Through a peculiarity of mapping, it's overseen by Monroe County commissioners, not the city — so Key West city commissioners had no power to control the camp there.

By 2001, the place was happening. A girl who called herself "Road Dog" wrote an online account for digihitch.com, a vagabonding Web site. She described dinghy rides to the island from Key West. A French girl taught her to crochet and how to ask tourists for spare change. A guy named Jack had a dog that caught fish. A Cuban rafter who squatted there erected a "two-story teepee" and invited her for potluck dinners. Grateful Dead fans built a "jungle-gym trail through the trees," Road Dog recalled. "Australian pines are easy to climb, and when you get near the top of one, you can sway to the next tree like a monkey! It's great!"

Adds Dale Pritchard, a sword swallower by trade and onetime Christmas Tree live-aboard: "It was crazy out there. I once saw a guy onshore shoot at a guy in a dinghy with a .22 pistol. Then the guy in the dinghy fired a flare gun into the other guy's boat, and the boat caught on fire."

By 2003, Key West had become an island of haves and have-nots. While bums filled the city's beaches and the island, Buffett's Duval Street eatery, Margaritaville, sold $34.95 flip-flops to tourists. City leaders made another try at cleaning up the place by proposing a measure to ship the homeless to Miami. "Here we are advertising as a relaxed, laid-back scene, a place where you can leave your troubles and stress behind,'' then-Mayor Jimmy Weekley told the New York Times, "and you get here and there are all these people on the street, and it puts your stress level up again.''


The only restaurant on Sunset Key is Latitudes. The beach bar/upscale hotel-restaurant is loosely named after Jimmy Buffett's song "Changes in Latitude, Changes in Attitude." Attire is "country club casual," and the menu is Floribbean themed — with a $32 pappardelle di mare entrée and a $39 Florida lobster platter. There's a stunning view. From the outdoor tables you can gaze at the sunset and nearby Christmas Tree Island at the same time.

The restaurant is arguably the most exclusive eatery in all of Key West — you need a boat just to get there — so on May 10, 2007, when three members of the Monroe County Commission were invited there for dinner, they were probably thrilled. Their host was Sunset Key developer Michael Walsh, who had also worked on scads of other luxury properties around Florida.

The guest list was a who's who of Key West: city Commissioners Clayton Lopez, Danny Kolhage, and Harry Bethel; Police Chief Bill Mauldin; and local lawyer/lobbyist Bob Dean. The dinner was reportedly a farewell soiree for Bethel, who was retiring from the commission after 20 years of public service.

But there was an underlying flavor of unseemliness. Florida law prohibits two or more members of the same commission from gathering to talk about city business without advertising a meeting and inviting the public. And host Walsh had recently partnered with Roger Bernstein, a Coral Gables lawyer, to develop Christmas Tree Island.

Just nine days earlier, on May 1, the city commission had voted 5-2 without much fanfare to annex Christmas Tree Island. The property's owner, Bernstein, had proposed the annexation. Bethel, Kolhage, and Lopez had been the critical votes. A second hearing was needed to make it official.

Here's where the story gets a little bureaucratic and convoluted, as most shady government deals do. In order to develop his isle, Bernstein and his partners — including Walsh — needed the land to be part of the city of Key West and not part of unincorporated Monroe County. The county's zoning laws allow for only two homes to be built on the island. Under Key West zoning laws, up to 168 units could be constructed there. Christmas Tree could become another Sunset Key, Bernstein and the developers had told the commission.

The numbers seduced some of the officials. By annexing the property, the city hoped to garner tens of thousands of dollars in tax revenue. Commissioner Bethel told the Miami Herald: "You can leave a bunch of homeless people camping out there now, or you can develop and gain revenue from it. It's simple economics as far as I'm concerned.''

The dinner apparently went off without a hitch. Bethel and Kolhage didn't return calls or e-mails seeking comment for this story. Lopez claims he couldn't remember what he ate. He contends the commissioners didn't discuss county business or the annexation of Christmas Tree Island. "We did talk about a fire that had taken place out there recently as the result of some homeless," Lopez says.

Five days after the Latitudes fiesta, Key West commissioners took up a second and final vote on annexation of Christmas Tree Island. Though Mayor Morgan McPherson (who had voted for the annexation) and Commissioner Mark Rossi (who had voted against it) were not present, Bethel and Kolhage wanted to vote on the matter right away. But the others, including Lopez, prevailed and the vote was delayed until July.

Before another meeting could be held, word of the Sunset Key dinner spread through town; someone, possibly a restaurant worker, another diner, or a person at the dinner, began to sing like a bird. Calls were made to local newspaper reporters, who sputtered in outrage.

"If you're wondering what this is all about," fumes Dennis Reeves Cooper, editor of the scrappy Key West the Newspaper, "here is the simple explanation: It's about helping a small group of already-rich developers make a few more million dollars."

Soon after Cooper and others published stories about the dinner, resident Erin Herwig filed a state ethics commission complaint against Bethel and Kolhage. Lopez, she believed, had been duped into going. "The lame excuse that the party was for the purpose of recognizing the services of one of the commissioners who wouldn't be leaving public service for another five months just doesn't wash," she wrote.

The backlash from the dinner was swift. Bernstein (who wasn't at the dinner) and Walsh withdrew the annexation request at the July meeting. "Basically we're reassessing the situation," Bernstein told the Key West Citizen. He refused to talk about the island's future with New Times, saying he is a "private person" who doesn't want his Miami neighbors to know his business.

Still, the episode left residents shaking their heads, convinced that officials were hell-bent on pricing every last working-class person off the island. "We're selling this town out to the rich," grouses Commissioner Rossi, who might be motivated to vote against development because of the parties he held on the island. He suspects his anti-development stance was the reason he wasn't invited to Sunset Key that night in May. Even Commissioner Bethel felt the citizens' ire. As he prepared to campaign for a seat on the town's utility board, he returned $1500 of campaign contributions from developer Walsh and his family because of the pending ethics complaint.

Meanwhile one Key West resident wanted to ensure that voters, not city leaders, would decide the future of Christmas Tree Island.


At age 66, Bruce Ritson is a strapping man, even though he has survived colon cancer and the amputation of his right leg. He's been having trouble with his prosthesis lately, so he spends most of his days inside, sitting in a plush orange chair under a lamp in the cool, dark living room of his house on a quiet street in the city's south end.

He thinks political corruption has become a way of life in Key West and Monroe County. And he's right: Former Monroe County Mayor John London died last year before he could be sentenced in a plea deal on charges of tax evasion. Former County Attorney James Hendrick was found guilty in February 2007 of witness tampering, conspiracy, and obstructing a federal grand jury. In 1995, Key West Commissioner Emery Major pleaded guilty to bribery and extortion charges for attempting to get city contracts for a water bike and taxi company; then-Mayor Dennis Wardlow (who famously spearheaded the city's secession from the United States to become the Conch Republic) was also charged in the scheme but later acquitted.

Back in 1975, Key West's fire chief, Joseph "Bum" Farto, was convicted on drug trafficking charges — but disappeared before his sentencing. (Then-Key West City Attorney Manny James was arrested in the same dragnet that took down Farto, but the charges were eventually dropped — although James was arrested a few years later and convicted of conspiracy.)

The mid-Eighties were a boon for indictments and scandal. In 1980, the Miami Herald revealed that then-State Attorney Jeff Gauthier used drugs, so Gov. Bob Graham removed him from office. Key West Police Chief Raymond Casamayor was convicted of protecting drug dealers — which eventually resulted in the entire city being declared a criminal enterprise under the federal RICO, or racketeering, statute, according to the Citizen.

Ritson moved to Key West from New Jersey in 1977 — just as the weirdness was getting started — and opened an accounting office. He had a thriving practice before the cancer. He befriended everyone, it seemed: judges, lawyers, the local homeless guys, and the clerk behind the counter at the drugstore. He still loves the quirkiness of Key West, even though that image has resulted in a hefty tax bill and a $12,000-a-year homeowners' insurance tab.

He looks tired, but his blue eyes — framed by years of laugh lines — sparkle mischievously when he pulls out a worn clipboard with some sheets of paper attached. "Here it is," he says, grinning. "Here's the petition."

Like many longtime Key West folks, Ritson was appalled — as he had been about the many previous scandals — by the politics surrounding the Christmas Tree Island vote. Ritson hasn't been to the isle in years, not since he took a girlfriend there on a boat in the late Seventies to smooch on the beach. He believes the place should be turned into a properly maintained park.

The former accountant doesn't think it would be fair for already-cash-strapped Key West residents to shoulder the police, fire, and garbage services for a bunch of new luxury homes. So in July, while sitting in his orange chair, he came up with an idea: What if the residents, not the commission, were required to vote on all annexation requests? What if the citizens had a say in what properties were accepted into the city limits?

Ritson, who attended Seton Hall University law school in the mid-Sixties, wrote the language for the petition himself. He knew getting onto the November ballot wouldn't be easy. He had only six weeks to collect 1521 signatures, or 10 percent of the voters who cast ballots in the last election. So he asked a dozen friends to gather signatures for a ballot referendum. Among them was longtime Keys politico Shirley Freeman.

Freeman first went only to friends' homes and asked them to sign the petition, but then she realized that wasn't enough. She changed tactics and visited local offices and grocery stores. In her 36-year political career, which included an eight-year stint on the Monroe County Commission and three years as county mayor, she had never seen such lopsided public opinion on an issue. "Everyone wanted the public to have the final authority over whether the island, or any other property, should be annexed or not," Freeman says. "There were only two people I talked to who wouldn't sign, and they said it was because they worked for the proposed developer of the property."

People were especially concerned about what would happen to the 100 or so live-aboard boaters who anchor off Christmas Tree Island. "That's the last bastion of affordable housing in Key West," Freeman says. "People just think it's ridiculous to build condos out there just so people from somewhere else can live in them a few weeks or months out of the year."

She eventually collected 400 signatures.

Even Ritson pounded the pavement. He used crutches and rode with a friend to a Publix supermarket on Roosevelt Avenue, where he hung around for four hours to collect a few dozen signatures. Then he sat outside the post office in a lawn chair on several hot days. "There was a disgust over the sneakiness of the commission," he says of the hundreds who signed.

By August, he and his friends had collected 2105 signatures, more than enough to put the referendum on this week's ballot. "I don't like dishonesty," he says. "People are allowed to be ignorant, but not greedy."

Indeed he believes greed has taken over his laid-back Valhalla. Key West is the most expensive city in the state; the average sale price of a home on the island in 2005 was a whopping $949,000.

Ritson chuckles when he thinks of how his referendum — if approved by voters — will derail future development in Key West. "It must really upset [the developers] knowing that this was all done by a one-legged man sitting here in his chair at home."


This summer a few dozen Key West do-gooders volunteered their boats and time to gather garbage from the island. A few weeks later, Walsh and Bernstein's people staked shiny new No Trespassing signs in the ground, and folks stopped sleeping there for fear of getting arrested. These days even the 100 boaters who anchor nearby don't venture ashore to cook out or play ball.

The island is returning to its wild state, overgrown with native scrub brush, crabs, and migrating birds. The Australian pines are all dead and gray, creating a ghostly forest amid the low-lying greenery. The paths that squatters once used have been overgrown by vines and bushes; it's nearly impossible to walk more than 10 feet into the island. Only a carved wooden statue that looks like a Polynesian tiki head remains on the shoreline.

A couple thousand feet away, on Simonton Beach in Key West, four homeless guys sit and stare at Christmas Tree Island. One of them, Lonnie Belk Helms Jr., is 47 years old, shirtless, and toothless, and hails from Daytona Beach. His face and torso are covered in yellow and blue chalk, probably because one of the younger vagrants was drawing pictures with the chalk on the floor of a nearby public bathroom and Lonnie rolled around in it.

Dave, a 49-year-old dressed in camouflage who looks like Edward James Olmos on a bad day, sits next to Lonnie on the beach. There's also Mike, a 26-year-old from St. Pete; and Denver, a 22-year-old from Kentucky. Denver, who has a thick, black beard, works nights at a local bar, dressing up like a pirate and standing at the door to lure in tourists. All are tattooed and smell of smokes, beer, sweat, and feet.

Each one has stayed on Christmas Tree Island at one point in his homeless career. Lonnie, the most talkative and obviously drunk of the four, says he partied out there a lot and once lost his flip-flops on the island. He also claims he tried to swim there a month or two ago but was stopped by a lawman pointing a shotgun at him. Lonnie is no stranger to the county jail; his most recent arrest came after he stole a six-pack of Coronas, some limes, and a bunch of bananas.

To develop the island, the men say, would be a sacrilege to the locals and to nature. "What's that little bird that lives over there, man?" Lonnie asks no one in particular.

"The osprey?" Denver replies.

"No, man, the little guy, who, ya know, the little dudes that run on the ground." Lonnie moves his index and middle fingers in a walking motion.

No one answers him. Everyone looks glumly at the island, now kissed by soft peach sunset hues.

"It's beautiful there," says Lonnie. "But they're going to take it away. Maybe not this year, but someday. It's all about the money."

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