A Pirate Looks at 400

Deep sea fishing a few decades ago in the Florida Keys

One of my dad’s favorite songs later in life was Jimmy Buffett’s “A Pirate Looks at 40.” If you’ve never heard this bittersweet ballad, it’s a love letter to the dreamers—especially those who wake up one day and realize the life they imagined never quite materialized. A few lines say it all:

Yes, I am a pirate, two hundred years too late

The cannons don't thunder, there's nothin' to plunder

I'm an over-forty victim of fate

Arriving too late, arriving too late

Both of my father’s parents died young, and he was left to fend for himself early on—eventually leaving his stepmother and siblings in his teens. Years later, he found a sense of kinship with Buffett through a rekindled bond with his two half-brothers who lived in the Florida Keys.

Jim and Thad were cut from a different cloth and embodied the spirit of the pirate in Buffett’s endearing song. Jim was a deep-sea fishing captain who started each morning with a Canadian Club and Coke before hopping into his El Camino to head to the dock. Thad? Well, let’s just say he was “different.” An incident involving a gun, a bank, an ex-wife, and some prison time made him strangely intriguing. My mother said not to ask questions.

The Keys hum with a particular kind of eccentricity and have always drawn the misfits and mavericks. Hemingway wrote there. Tennessee Williams wandered the streets. Hunter S. Thompson probably still haunts the bars. While our uncles weren’t quite as renowned, my brother John and I thought their stories were treasures in their own right. Once, they found a bale of marijuana floating in the Gulf—only to get ripped off when they tried to sell it to the mob. One of Jim’s favorite lines was: “(Insert name of game fish here) is great smoked, but you can’t find rolling papers big enough.”

In our teens, John and I loved traveling down to Marathon to experience a side of the country that felt both stunning and a little dangerous. The first time I heard “A Pirate Looks at Forty” was in a small skiff, fishing for tarpon at night under the A1A bridge. On that trip, a massive hammerhead kept taking bites out of the 100-pound tarpon we managed to land—scaring us both silly as the fish thrashed in the dark Gulf waters.

There’s something about that youthful feeling of wild adventure—of not being in control, with your entire future stretched out ahead. We tend to look back on those moments with a deep and affectionate nostalgia.

This past week, I spent a few days in Sarasota with friends we’ve known for decades. I observed a few 40-something buccaneers hoisting bifocals instead of the Jolly Roger—tech-weary, listless, emotionally adrift. Age takes its toll. And I couldn’t help but wonder if, over time, we all trade in our swashbuckling chaos for something quieter, colder. Greenland Sharks live for over 400 years, swimming alone, slow and steady, always keeping their bearings.

On our final night in Florida, I sat across from my friend’s father, Dave, who’s in his late eighties. Dave was a Chicago attorney for years and once made a record fifteen free throws in a row on his way to a 41-point high school basketball game. We talked about alternative music (and his disdain for Depeche Mode), his love of jazz (especially the legends he knew from Chicago’s Blue Note Jazz Club in the 1950s), and this year’s NFL draft winners. After dinner (a foot-long hot dog dipped in batter fried to a golden brown and a beer), Dave hopped in his car and drove himself home.

In a few weeks, I’ll be attending the 90th birthday celebration of our friend Martin—a contemporary of my father who baptized my son and married my wife and me. As a Methodist minister in the 1960s, Martin worked closely with Martin Luther King Jr. and Jesse Jackson on Operation Breadbasket and other landmark civil rights efforts. These days, he still drives, has his opinions published in local and national newspapers, attends the symphony regularly, and exercises along the lake.

Every Saturday, my wife works with a gentleman I’ll call Walt. At 88, Walt walks to his Loop office six days a week to manage his many affairs. Over the decades, he’s led global companies, became the first American to sit on the board of a European automaker, knew Donna Summer before she was Donna Summer, and remains connected to the world’s movers and shakers in ways I only read about in magazines. And yes—he still drives too.

I’ve been lucky to know men like these. I’m inspired by their love of life, family, and strength without showiness. Think of all they’ve lived through—decades of upheaval, progress, and change—and yet they greet each day with a quiet, rebellious spark, living by their own code.

So I ask: As a Greenland shark, what keeps you engaged as you traverse the seas of life? What adventure still calls to you from just beyond the horizon?

Because if a Greenland Shark can end up in the Caribbean after centuries of slow, steady swimming, then maybe—just maybe—400 is the new 40.