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Return to Key West: Part Two, R.I.P. Captain Tony

Posted on by Harry Ramble
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Outside the Green Parrot. In 1992, I think.

I was in a convenience store on Caroline Street, Sunday after the post-race party, a six pack of Fiji water and a laughably overpriced mini-bottle of Aleve in my hands, watching as the proprietor punched out tickets on the lottery machine and talked to the guy in front of me, a fortyish guy in cargo shorts, cap, and boat logo T-shirt.

“How’d it go, last night?” the proprietor asked.

“Bad,” he said. “Bad again. It was hardly worth going out.”

“It’ll turn around,” the proprietor said, with little enthusiasm. “I keep hearing on the news. The economy has already bottomed out.”

“Screw the economy,” the guy in front of me said. His shirt advertised Key West sunset cruises. “We’re all waiting on Cuba. Once Cuba opens up, we’ll all be sitting pretty.”

“Ah, Cuba.” The proprietor handed a couple of tickets to the boat guy. “There’s always Cuba.”

“I hear from people on the inside, it’s a year and a half away, at most. These are people who know.”

“Sure, I hear that, too. How long can it be now?”

I’ve been hearing a variation on this conversation in the Keys for twenty years. Cuba is the Holy Grail for anyone who runs a tourist boat business in Key West, and it’s a portent of doom for anyone who runs a bed-and-breakfast or a gift shop. There are very few people left on the island who remember what Key West was like when Havana was a legal destination for American tourists. I talked to one of them once, about ten years ago, on a casino boat in the waters off Key West.

Florida law mandates that casino boats have to go a certain number of miles offshore—I think it’s three—before they can turn on their slot machines and start dealing cards. We were returning from one such trip when I went to the back of the boat to count what little money I had left.

“I hope you didn’t put any money into one of those machines,” someone said.

I saw that Captain Tony Tarracino was sitting on one of the two seats in the stern. I’d seen him earlier, playing multiple hands of blackjack at a modest five bucks a pop. I knew who he was from the times I’d seen him on a barstool in the Saloon he’d run from 1961 until he’d sold it in 1989. Captain Tony is as close to an iconic character as Key West has ever had. Much more so than Jimmy Buffett, who, though associated with Key West in popular culture, moved away from the island in the mid-1980s.

“Not me,” I said. I took the other seat in the stern. The exhaust from the laboring boat engines was a miasmic gray cloud between us. Tony was wearing neatly pressed slacks and a polo shirt. It was a cool night on the water, in early January. “I stay away from the machines.”

“There’s three kinds of machines,” Tony said. “Loose machines, tight machines, and outright thievery. Those back there,” he hiked a thumb at the little gambling area behind us, “are the third kind. If they could jack the card games, they probably would. Hell, they probably do. This is a tight boat. They don’t let you go home with nothing.”

“Why do you come out then?”

Tony shrugged. “It’s the only game in town, I guess.”

I grinned at this gambler’s logic. Legend has it—and every statement made about Captain Tony Tarracino could and should be prefaced with the phrase Legend has it—that it was gambling that brought him to Key West. It’s said that Tony and a friend figured out a way to pick up New Jersey racetrack results on a shortwave radio just early enough to get bets in on those same races with Newark bookies. They won a lot of money in very little time, which earned Tony a trip to a Newark dump where goons beat him up and left him for dead. That was in 1946. Weeks later, he is said to have arrived in Key West on a milk truck with $12 in his pocket. Once there, he worked as a boathand, a captain of his own shrimper, a gun runner, and, in 1961, the owner and proprietor of Captain Tony’s Saloon on Greene Street. The bar is popularly advertised as the “Original Sloppy Joe’s Bar,” but it was standing empty in 1961 when Tony bought it. Immediately before that, it had been a gay bar that catered to sailors from the nearby naval base until the Navy placed it off-limits, thus ending its viability as a moneymaking enterprise. Tony owned and ran the bar from 1961 to 1989, when he sold it upon being elected mayor of Key West.

“It’s the only game in town until they open all that again.” He gestured vaguely out over the waters around us.

“All what?” I said. I didn’t know north from south.

“Havana,” Tony said. “Cuba. They open all that again and Key West will go back to being a few shacks, an airstrip, and a shitload of mosquitoes.” He started in, then, on one of his oft-told stories, some misadventure off Cuba during the Bay of Pigs. I recognized the story as one he’d told many times from his usual station by the cash register in the saloon that still bears his name, a saloon he visited regularly for twenty years after he sold it, to sign T-shirts and pose for pictures with tourists.

Tony Tarracino had arrived in Key West just after the worst of the Great Depression years, but he would have known many people who’d lived through the island’s lean years when virtually every year-round resident was on some sort of government relief. The history of Key West has been revised and reinvented many times, and the 1930s are now summed up primarily by tales of Ernest Hemingway and big fish stories. The truth is that the island was desperately impoverished in the 1930s and the few viable businesses on the island included a couple of bars with illegal gambling in the back, the Pan Am mail and passenger service to Havana, and a few notorious brothels at the southern end of the island.

As Tony was telling his Cuba story, two girls in their early twenties appeared in the back of the boat. Tony had been talking to them earlier at the card table. One of them had gotten a pen from one of the boathands. They had decided they wanted autographs. Tony took the pen and one of the girls turned around and lifted the sweatshirt she was wearing to ward off the chill. Underneath, she was wearing a tiny bikini bottom. Tony signed one bikini bottom, then the other. We watched the girls scamper back up the ladder to the bar above us.

“I’ve signed a lot of asses in my day,” Tony said.

Tony talked for a little while longer. He graciously shared a couple of card-playing tips with me, both of which eventually lost me considerable money until I abandoned them. When we pulled up to the boat slip, he was the first one off the boat, helped by two mates. He would have been about eighty years old then; he’d fathered his last child, with his fourth wife, a woman half his age, at the age of seventy.

In Captain Tony’s. February, 2010.

The bar he owned and/or presided over for almost fifty years has always prided itself on being a bit of Old Key West, even as new Key West grows ever more upscale around it. This, of course, was never really true, at least in the years that I knew it. Captain Tony’s Saloon is one of the triumvirate of bars—the Hog’s Breath and Sloppy Joe’s being the others—that every cruise-ship daytripper makes a point of hitting on their three-hour sojourn on the island. At night, the bar is taken over by young people, kids who seemed young to me even twenty years ago, who favor the sweet rum punch doled out in souvenir Captain Tony’s plastic cups and get their bras and bikini tops stapled to the rafters. I can’t remember anything of consequence ever happening to me there, though I did see the deciding game of the 1995 Mariners-Yankees playoffs there, the thriller that represented Don Mattingly’s first and only sniff of post-season play in his between-the-glory-eras career.

Captain Tony passed away a little over a year ago, in November of 2008, at the age of 91. He was the island’s last link to an age before Disney cruise ships and Fantasy Fest parade floats sponsored by Captain Morgan rum and MetLife insurance. He’ll be sorely missed.

So. What else?

I saw on the ride down that the Caribbean Club bar at Mile Marker 104 in Key Largo now has a massive, imposing neighbor in the form of Jimmy Johnson’s Big Chill. Johnson, of Miami Hurricane and Dallas Cowboy championship fame, is probably the Keys’ biggest resident celebrity these days, and his new venture will surely steal whatever tourist traffic the Caribbean Club was getting. I stopped in at 11:30 on Saturday morning, en route to Key West in a rented Nissan Xterra, and found the usual crowd of locals already holding down every stool around the bar. I used the restroom, bought a can of Miller Lite for a dollar and took it out back to where other locals were struggling with boats on the boat ramp. The Caribbean Club’s small claim to fame is that its location was used to film exterior shots for the Humphrey Bogart film Key Largo. They might be selling less of those Bogey T-shirts in the near future.

And the race. The Key West Half Marathon. It was a beautiful course around the perimeters of Key West and Stock Island. I realized a half hour before race time that I’d left my iPod headphones in my car back in New Jersey, so I ran the race without musical accompaniment. It was an interesting experience, something I may try again. On purpose next time. Final tally: 13.1 miles, 1:59:23.

I did manage to close down the Green Parrot one night, Monday night, though I was only able to do so by napping from 9pm to 1am, then getting out of bed and arriving at the Parrot at 2am. The Parrot has not one but two 24-hour webcams in place now—something its management once insisted it would never have—and an upscale little boutique next door that sells the T-shirts that used to be jammed into a plastic bin beneath the bar, as well as all manner of kitschy coffee cups, frameable prints, and refrigerator magnets. It’s still open ’til four, and they’ll still put your last beer in a plastic cup for the road.

That was my only late night “adventure;” I sleep a lot more now when I’m away. I find more and more that the willies have a way of seeking me out if I become stranded between here and there. I’m much more susceptible to unease when I travel alone—I feel more alone—than I ever did in my twenties and thirties. The dreads come stalking me even as the bartender in some airport or casino or restaurant bar sets a first glass of beer before me. Sometimes that unease can spiral out of control, and I’ll find myself trapped in a place I don’t want to be, watching the Weather Channel repeat itself in endless loops, and making phone calls I shouldn’t be making. These days, I find it’s best to have always in front of me some destination or goal. I don’t have to be there yet, engaged in that activity yet, but I like to know it’s there, orienting me, drawing in the slack of the unpurposed time before me.

On my way out, on Tuesday, it was 75 degrees and sunny in Key West. I like to drive into Key West, but I take the puddle jumper out. When I arrived at the airport, I saw that it has been completely remodeled and expanded. The old Conch Flyer, the airport bar that once opened onto the tarmac, is now on the other side of the airport access road, attached to a new parking deck and connected to the departure gates via a long elevated walkway.

For a long time in Key West, the Conch Flyer was the bar of last resort. When every other bar was closed at 4am, the Conch Flyer, due to some odd Keys law governing airports, was allowed to stay open 24 hours. As a result, the Conch Flyer became a haven for off-shift strippers and bartenders, late-night oddballs, and purveyors of the kind of controlled substances of interest to people who are still drinking at 6am. Tourists flying out of or arriving in Key West would sometimes find themselves in the midst of last night’s party, still continuing unabated at the Conch Flyer at 8am.

The new Conch Flyer is an anonymous airport bar with some Pan Am gear on the walls. As I finished a beer and prepared to meet my plane, the barmaid was wiping down the bar and preparing to close out the register. I was the only patron at the bar.

“Going off shift?” I said.

“Oh, no,” she said. “We close at seven.”

“PM?” I said.

She smiled at me like someone hearing the same comment for the thousandth time. “Yes, PM,” she said.

Overhead all the TV monitors were tuned to the Weather Channel, which showed an ice storm looming over South Carolina and temperatures in the low 20s back home in New Jersey. I shouldered my bag and headed for the new, improved transportation security area.

Sleeping With The Angels

Posted on by Harry Ramble
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KWG2I don’t think anyone sleeps in the Key West Cemetery anymore. Key West cops are much more like cops anywhere else, now that Duval Street is no longer mostly abandoned storefronts from the Wreckers Museum to the Southernmost Point, and $500K won’t buy you a modest conch house.

But this was 1992 and I was six days into a five-day trip to Key West that was already four days too long and getting longer.

I was sitting at the downstairs bar of the Bull and Whistle, perched on a stool behind a Rolling Rock and three Bayer aspirin set out on a cocktail napkin by the bartender, who kept a jug of them beside the cash register. It was a little before 11am.

I’d just checked out of my hotel, left my bags at the front desk, and handed the rental car key to the guy I’d driven down to Key West with five days before. I told him I’d see him in Miami, walked out into the morning sunshine on Duval Street, and down to the Bull.

The Bull is the lower bar, billed as the last of the old-style open air bars on Duval, and the Whistle is the upper bar, with a balcony well-suited for watching the street parade below during tourist season. This was early October, though, and I had the bar—and the town—mostly to myself. The Bull offers two experiences to its patrons. It can be a lazy, dim, quiet, breezy place to sip a beer in the company of one or two old guys reading newspapers. Or it can be packed right out to the street with cruise-ship day trippers in crisp new Conch Republic T-shirts, holding 2-for-1 margaritas in both hands and calling out Jimmy Buffett requests to the house musician. This, happily, was one of those former times.

I was in Florida with an old friend from college and two girls we knew. One of the girls was an old girlfriend of mine; the other girl had some kind of unresolved issue with my friend. It was a bad situation made worse by some poor decision-making on the part of me and my ex. We’d hooked up within an hour or so of arriving in Key West and had been carefully avoiding each other ever since. Thus, we’d added one more psychological subtext to a vacation that didn’t need anymore psychological subtexts. For five days, the air had been thick with subtexts.

The other girl had responded to this awkward situation by being plucky and upbeat and generally cheerful. My friend, who had his own issues, as I’ve said, responded by saying nothing to no one for five days. I hadn’t said goodbye to the girls. If this was Friday, I hadn’t seen either of them since some time on Wednesday.

But the bar was quiet, a light breeze was up, and all three of them were some miles east of me by now, my college friend on Route 1 through the Keys, the girls in the puddlejumper to Miami airport. My headache wasn’t any worse than any of the others I’d had in recent days, and I had seven hours to myself until the girl I’d met the previous night would be off her day shift at a restaurant on Stock Island.

She was short, with dark hair, and a wide, solemn face, and I think her name might have been Sara or Susan. We’d met at the bar in the Green Parrot in the way writers always meet. By telling each other stories. I told her some preposterous and long-winded story about a far-future miner for artifacts trapped in a rejuvenation machine, a story I later had the good sense never to write, and she read me some poems written on the backs of blank guest checks.

We watched the band until the band packed up and left, and then drank at the bar until the bar drew closed its shutters at 4am and threw us out into the pre-dawn darkness of Whitehead Street. By the time the bright pink Key West cab dropped us off in front of her place on Truman Street, above a used bookstore and directly across from a go-go bar called Lookers, the morning’s first roosters were already crowing at us and pecking at the curbside trash.

She didn’t have her own room, just a mattress on the floor behind a folding divider printed with Oriental symbols. Don’t worry about noise, she said, her roommates kept her up half the week. For the next few hours, I could hear them, pointedly not listening to us. At 10am, she wrapped the sheet from the bed around herself and led me by the hand to the wooden steps at the side of the building, down the steps, and then pushed me out into the street. “Come back at six,” she said, “I’ll be off work by then.”

In the Bull, I finished my beer just as the first group of giggling old ladies in funny hats walked in off the street, ribbing each other about being “hardcore morning drinkers.” Soon they were followed by their husbands and plenty more boisterous middle-aged day trippers. The musician that day, a guitar player named Michael McCloud whom I’ve since seen many times at the Schooner Wharf Bar, folded his newspaper, filled a big plastic cup with water and ice, and climbed up onto the stage. I left the Bull at noon, drunk again, and lightheaded with sheer weariness.

Key West Cemetery, Duval Street, Green Parrot BarI crossed Duval, went over to Simonton, and south to the Atlantic side of the island. I had a general notion of getting something to eat down toward Truman Street, but I cut over onto Angela Street and only got as far as the cemetery. Back then, the Key West Cemetery was already a fairly popular tourist destination, and it’s much more so now. But it was the very beginning of October, and the cemetery was deserted under somnolent midday heat, silent but for the cackling of roosters and the buzz of cicadas. I entered at Passover Lane and walked up one of the wide lanes through the grounds.

Most of the graves in Key West Cemetery are aboveground vaults of marble and stone. It’s too difficult and expensive to dig very far down into the coral that lies beneath the island turf. Standing in the middle of the cemetery, it’s like you’re standing in the midst of a city of the dead, with its vaults piled on top of vaults, and the elaborate statuary—angels and cherubs and obelisks—reaching up to the sky.

When you read about Key West Cemetery or go on one of the tours, much is made of the offbeat epitaphs and decorations (“I Told You I Was Sick,” “I’m Just Resting My Eyes”), as if the cemetery were another manifestation of the island’s much-advertised quirkiness. But that non-conformist ethos doesn’t appear in Key West until the ’70s, when the gay and lesbian crowd embraced Key West and lifted it from its post-Navy-base doldrums. The vast majority of the graves in the Key West Cemetery date back to much earlier times, from the 1880s to the Great Depression. Key Westers in those years didn’t have time for quirkiness. They lived hardscrabble lives on a very isolated island. During the Depression especially, virtually everyone on the island received some form of government assistance and the island was so poor it was scarcely illuminated at night.

So what you see as you walk among the vaults are gravesites that have been customized over time by descendents who visited often. Many of the vaults have stone benches, built to afford visitors rest and reflection. A significant number of stones and vaults bear artists’ renderings of the deceased. And then there are the epitaphs. Not just names and dates, but short life stories carved into the stone.

Why? Because on an inaccessible island like Key West, where there was nothing much to do but fish the sea, fight the mosquitoes, and fend off the storms, you visited the dead. And you visited them often. Spanish sailors named the island Cayo Hueso, Bone Key, when they found it, because it was littered with the bones of a vanished Indian tribe.

I walked through the rows for a while, reading the inscriptions, until I found a wide, comfortable-looking vault. Entombed inside were the remains of a Hispanic man and wife, probably Cuban. There are many, many Cubans buried in Key West Cemetery, and the grounds include a separate area set aside for Cuban Freedom Fighters. The husband died in his forties, just after the Second World War. His wife died forty years later, in 1987.

The little representations of them, painted on small ceramic ovals embedded in the stone at the head of the vault, showed them at the same age, both in their forties. How many times over the years, I wondered, did that woman come to sit here at her husband’s side? What were those last years like, that she commissioned this small image of herself, forty years younger, as her last word to the world? Atop the monument, a beautifully rendered stone cherub cavorted.

I plucked a wreath from an adjacent stone and set it at the head of the vault. Then I stretched out, my head propped by the wreath, the cherub standing sentry above me, and I fell instantly asleep. I had the most vivid dreams. They’re all nonsense now, not worth describing, though I still remember them distinctly today. Suffice to say, I slept with the angels.

Key west, angel, cherub, gravestone, duval streetI slept for six hours straight without stirring and woke at dusk, feeling like I was sitting up in the midst of an ongoing dream. The breeze was gone; the roosters and cicadas were silent. The light seemed wrong, like it was leaking up out of the ground, instead of radiating down out of the sky. And though the sun had already set and the light was fading, the edges of every tomb, every stone, every leaf, were very clear and precise. The air possessed a mute, dumbstruck quality, like in the aftermath of a photographic flash. My ears, I realized, were hurting me, and I swallowed to release the pressure that had built up inside them.

I looked up at the sky and in that very second it started to rain. It rained like someone was pouring a bucket over my head. I was soaked to the skin in an instant.

I ran down through the cemetery and hopped the fence at Grinnell Street, running full tilt to Truman Street. I ran to the apartment above the used book store, pounded up the wooden stairs, and rang the bell. The girl opened the door and looked out at me.

“You’re still wearing the same clothes,” she said.

“I know, I’ve been wearing them since Wednesday. Think of this,” I stretched my arms wide in the downpour, “as the rinse cycle.”

And then we went out into the storm—which, I found out later, had a name, Tropical Storm Earl—and did it all again. The next morning, I pulled on my still-soaking-wet shorts and she gave me one of her shirts, a black tank top printed with the logo of a long-defunct 80s-era Key West gay bar.

“Come back at six,” she said, though she surely knew I wouldn’t be back, and I agreed. “Six o’clock,” I said.

Outside, the storm was just letting up and I walked east two miles out onto North Roosevelt Boulevard, stopping at the first rental car storefront I encountered. They had no cars and I had to wait awhile for one to be returned. I drove east and caught up to the storm again at Marathon Key, an unrelenting, pounding deluge that obscured everything further than a few feet from my front bumper, all the way to Miami.