​My first time on Martha’s Vineyard was in 2016, when I visited with my college roommate, David McCullough III, for a long weekend in May. I had no conception of the place other than that it was a summer destination for people with roman numerals in their names, where many of my college friends had family compounds. David said we’d be going “golfing” and “mountain biking.” I soon discovered that meant we would tee up golf balls in Waban Park and race down Peaked Hill on one-speeds.

“The Vineyard inspires the imagination,” he said.

He also said we’d go visit his “uncle.” What he meant by that was we’d stop by an old junkyard in Vineyard Haven, filled with a phantasmagoria of rusted cars and painted wooden signs that advertised a moving and trucking company as if it was transporting P.T. Barnum’s savannah mammals.

“Clarence A. Barnes III, Movers,” the faded sign said, its three-layered serif font retaining just enough pop to be visible from the street. “Boston. New York. Washington. Ft. Lauderdale. Santa Fe. Hollywood.”

The American Pickers emporium continued inside, with stained glass speckling the light to create a kaleidoscopic effect on the wood and relics of the office. I felt transported to a different world, a world of magic and old-timey possibility. Trip wasn’t around, but the staffers brought us some swag: a pair of blue, Barnes Trucking shirts with the classic golden-yellow font. On the back were two hands, intertwined in a shake. It was my only souvenir from the trip, and I wore it everywhere afterward. Some day, I determined, I would meet this man, whose shirt I always kept close to my chest, reminding me of that first weekend of Vineyard wonder.

Two years later, in 2018, I returned to the Island to intern at the Vineyard Gazette. I brought my Barnes Trucking shirt and little else. But I didn’t get to meet the man until the fall, when I was assigned to cover the Creative Living Award during my first week as a full-time reporter.

What an introduction.

At the Ag Hall in West Tisbury that night, I received an education in Vineyard history and culture, as Allen Whiting, Ross Gannon, Chris Scott and others transformed the stage into Trip’s front porch, replete with rocking chairs and his famed, life-sized plaster dummy, regaling hundreds of Vineyarders with stories of sinking ferries, saloon shootouts, dead men in canoes, forgotten permits and other yarns.

“It shouldn’t be the Creative Living Award,” his nephew Billy McCullough said. “It should be the, Wow, You’re Alive? award.”

As it turned out, the hard-scrabble, chain-smoking enemy of regulators and building inspectors who had eschewed his Park Avenue childhood to become a milkman on Chappaquiddick was also the reason the Ag Hall was standing.

And I learned that Trip had a more serious side. He’d gotten sober in 1989, and that junk yard in Vineyard Haven served as an unofficial halfway house and place to dry out for down-on-their-luck Islanders, before he helped found the Island’s sober living facility. The ice arena wouldn’t have been built without him. And he’d raised millions as an auctioneer for everything from hospice care to Martha’s Vineyard Community Services.

Most interesting for me, as a young reporter, was that he was active politically, serving on a number of the Vineyard’s ever-proliferating boards, including the Vineyard Preservation Trust, the Martha’s Vineyard Commission and the Airport Commission. I got to know this version of Trip the best over the years, as he channeled the same rollicking, boundless and boundary-less energy to become a vocal — and loquacious — advocate for efficient government, workforce housing and preserving the Vineyard way of life. He was an asset for a reporter, much easier to get on the phone than off it, his quotes just as colorful as his trucks.

During my second year on the Island, there were a few major controversies at the Martha’s Vineyard Airport, including mysterious personnel issues and a rather secretive, potentially incendiary expansion plan. Trip ultimately resigned from the Airport Commission in frustration, and not long after, he called me, asking that I come over to his house in West Tisbury on a Saturday.

“I’ve got something for ya,” he said. “It’s about all this airport funny business.”

It was my first time at the famed house on State Road. We sat on the wrap-around porch and ate pieces of rotisserie chicken and nothing else, as he regaled me with tales of his youth. He asked if I had any interest in recording some of his stories, to help him write a biography. I was honored and said sure, that I would come over on weekends, but I didn’t take it as seriously as I should have. Eventually, I asked about the airport.

“Oh! The airport. Yes.”

He returned with a black, hinged and locked briefcase that looked like it came straight out of a John Grisham novel. It weighed about 15 pounds and was swollen, ready to burst like the buttons on a fat man’s shirt.

“Everything you need is in there,” he said, motioning to the briefcase. I was equal parts dumfounded and exhilarated at my Erin Brockovich moment. We shook hands before I left.

When I got home, I immediately tore open the briefcase to find that it was packed with decades of papers; hundreds of blueprints and meeting notes and unintelligible chicken scratch, disorganized and tattered. I sifted through it, wondering what it all meant, wondering what I could even do with it. In the next weeks other stories, and other records requests, came over the transom. The weeks turned to months, the months to years. I was young and I was stupid. I never followed up on Trip’s request to record his stories. There were other scandals and a pandemic that required my attention. I figured Trip would always be around.

Over the next few years, that black briefcase traveled with me as I did the Island shuffle. I could never get rid of it, and I’d occasionally look through it, believing in the back of my head that it contained some secret to the universe, or at the minimum, a good story. As time passed, the briefcase became my own sort of journalistic white whale, growing in mythic lore as its hinges strained with the promise of a future Pulitzer (fine, maybe a NENPA). Eventually, before I left the Island, I brought the briefcase back to Trip at the last Martha’s Vineyard Commission meeting I covered, admitting failure.

“What’s this?” he said, when I gave it to him.

“The airport commission briefcase.”

“I gave that to you? Well, I’ll be damned. Thanks for bringing it back, but I don’t need it. I’ve got enough old junk.”

I threw out the briefcase, but I kept the Barnes Trucking shirt. When I read that Trip died last week, I had an immediate pang of regret, remembering that I never went back to record his stories, that I was too young to know how fast life moves. I pulled the blue shirt out of my closet, its letters old and peeling, but the handshake still visible between a golden banner that said “Welcome” and “Barnes Trucking,” in the same serif font. I put it on, transporting myself back to his world of wonder.

Noah Asimow worked for the Vineyard Gazette from 2018 to 2022. He now lives in Pittsburgh, Pa.