
“Mother, mother ocean, I have heard you call
Wanted to sail upon your waters
Since I was three feet tall
You’ve seen it all …. You’ve seen it all.”
“A Pirate Looks at Forty”
— Jimmy Buffett
I fell in love with the song months before meeting the man, and I still don’t know whether to bless or blame Jimmy Buffett for subsequent events. That’s because the song was Buffett’s “A Pirate Looks at Forty,” a mesmerizing portrait of a charismatic, flawed rogue who didn’t fit in the modern world but would have flourished as an 18th-century buccaneer.
It was 1978 and I was 22 years old, an aspiring hippie desperate to disguise my naivete, when the pirate walked into my workplace — a Native American jewelry store owned by a New Jersey refugee who called himself Geronimo. It was an incongruous enterprise for Key West, but it occasionally drew customers.
That day they included the pirate, who told me his name was Phil Clark. He was a tall, dark-bearded man, twice my age, with an extraordinary vitality that made everybody else in the store look faded by comparison. He was the picture of devil-may-care confidence, wearing a small Spanish coin on a hoop in his ear and a curved turtle claw hanging from a cord around his neck.
Overall, he was pretty overwhelming to an unsophisticated 22-year-old. After work I met Phil at the rowdy Green Parrot Bar, where he focused all his charm on me, and someone told me he was the subject of the Buffett song I loved.
It felt like fate. By the time I found out he made his living smuggling pot, it was already too late; I couldn’t imagine my life without him.
For the next five years, I was known around Key West as “Phil’s lady.” Because of his larger-than-life reputation, that meant I was protected and looked after by his ragtag cohorts, who treated me like a little sister.
In many ways, Phil’s reputation was well-deserved. He was one of the daring Keys renegades whose exploits made him practically a living legend. He had tried almost every hazardous occupation known to man — from mercenary soldier to gentleman smuggler to New York City advertising executive. (The last, he told me, gave him the biggest twinges of conscience.)
He had lived in Key West since the 1960s and loved it unconditionally. He was wickedly intelligent, a man of great personal integrity and a voracious reader who held endless discussions with the island’s vagabond literati.
Phil and I shared golden days full of laughter and raucous nights drinking at the Full Moon Saloon — once, unforgettably, with “gonzo journalist” Hunter Thompson. He brought me teddy bears, Shel Silverstein books, and $40,000 in a shoebox after a particularly lucrative score. He asked me to marry him and I said yes.

Of course, our life wasn’t all good. There were vicious arguments and days when, facing the realities of Phil’s outlaw profession, I felt an uncontrollable fear slithering down my spine. Worst of all were the times he departed on unspecified “business trips” because in his business, there was no guarantee he would come safely home.
Eventually he got busted, because luck runs out even for legends. He was caught on a boat carrying 10 tons of “cargo” and locked up in an Orlando jail.
When he bonded out and came back to Key West, his vitality seemed quenched; he had made private plans to say his farewells and disappear. The last time I saw him it flashed through my mind that, in two years, someone would come to tell me he was dead.
I was wrong. It was only 18 months.
As Buffett foreshadowed in the eerily accurate final verse of “A Pirate Looks at Forty,” Phil drowned. He had been living on another coast, under an alias. It took weeks to properly identify him and bring his ashes home.
Yet his death was just one kind of ending. Even now, survivors of the “old days” still smile at the mention of Phil Clark’s name — survivors who were captivated by the stories he told, shared his adventures for a time and inherited his love of Key West.
We’re still here. And when the strains of “A Pirate Looks at Forty” drift out from a speaker somewhere, we still listen.