Somewhere in Key West’s Old Town, there’s an elderly man cursing the soul of Calico Jack.
I don’t mean Calico Jack Rackham, the infamous Caribbean pirate who was hanged in Jamaica in 1720. No, this Calico Jack was a slightly insane dog who shared the pirate’s name, and disrupted a secret gambling ring in 1980 with one larcenous flick of his tongue.
Jack was just a puppy when I found him at the Key West shelter. He had a black body, with brownish legs and long hound ears. Foolishly imagining that he would become a storybook companion like Lassie, I adopted him and brought him to my place on Margaret Street.
In those days Key Westers rarely locked their doors, and sometimes didn’t even close them. People wandered in and out of each others’ homes as if the Old Town district — with its unrestored Victorian houses and rampantly blooming flowers — was a giant commune.
In a sense, it was. Impromptu porch parties were common, full of laughter and tall tales and music, with cheap wine and joints shared with whoever stopped by. Money was scarce but fish were plentiful, and we always cooked enough for the friends who dropped in.
It was the ideal atmosphere for raising a puppy, I figured, with plenty of people around who could help me mold Calico Jack into a perfect island dog — one who followed me on random adventures, never needing a leash or anything more than a gentle command.
After all, other dogs behaved that way.
Friends took their canine companions to Dog Beach, the pocket-sized stretch of sand next to the beloved restaurant Louie’s Backyard, and watched their pooches romp in the water while they sipped cocktails at Louie’s After Deck bar.
Friends pedaled their bikes along Key West’s narrow lanes with their dogs riding in the baskets, grinning furry-faced grins. They were facetiously dubbed “basket hounds,” a breed indigenous to the island.
Calico Jack, however, was another breed altogether. He developed an air of madcap lunacy that worsened as he got older. Despite training attempts, he had no manners and no respect for personal space. And he was a thief, stealing food and small items as he roamed the neighborhood.
When he was almost a year old, my wayward pup committed the crime that earned him a lasting place in island lore.
The Margaret Street area was a lovely, eclectic mix of old homes and low-key businesses. Down the block stood Molina’s Bakery, where the smell of fresh Cuban bread perfumed the air.
Around a nearby corner was a shabby yet popular Cuban restaurant. Unbeknownst to me, its back room housed a gambling den where men gathered for high-stakes games of dominoes.
One fateful day, perhaps seeking a tasty handout, Calico Jack poked his nose inside.
I was oblivious, relaxing on my shady porch. That is, until Jack came pelting down Margaret Street carrying a domino in his mouth — chased by a stocky man who was shaking his fist and hollering, “Perrito sin verguenza! Puppy without shame!”
It was clearly a situation to avoid. Without a sound, I slipped into the house.
Weeks afterward, though I never understood the domino game’s rules, it emerged that Jack’s theft had cost his pursuer a substantial sum. That was a shame, but there was nothing I could do.
Now, decades later, the Cuban restaurant is long gone, as is Jack. I moved to another Old Town spot many years ago.
But the Margaret Street neighborhood is still lovely, appearing untouched by the passage of time. Biking past my former apartment last month, I could almost hear — from one of those wood-frame houses surrounded by flowers — an old man’s voice, still cursing “the puppy without shame.”
