PEBBLE BEACH, Calif. – Eighteen months ago, on a golden Sunday evening at the Presidents Cup in Montreal, Fluff Cowan’s mustache curled.
“Oh, I don’t know,” the legendary caddy said, his New England accent curdling the fear he felt behind a tuft of snow-white facial hair.
He paused and turned the idea over in his head again. In his 47 years as one of the most prolific caddies in golf history, he had been asked some strange questions, but none were as good as this one.
How could he capture the entirety of his caddying experience… in a single song?
“Well, I think the first thing that comes to mind is – in the way it ebbed and flowed….”
He paused again, painfully.
“I think I’ll have to go with ‘Truckin,’” he said.
The conversation progressed, but Cowan seemed stuck on that title, satisfied with his choice. It captured his spirit, his story and, critically, his favorite band: the Grateful Dead. A few moments later a grin appeared on his face.
“I was just a driver crazy.“
Cowan turned 78 on Saturday, two days before the start of the golf tournament that also feels like the start of a new year: the annual AT&T Pebble Beach Pro-Am. But the start of this golf season in Northern California in 2026 has lost some of its tie-dye brightness. In early January, the world learned of the death of one of Cowan’s heroes: Bob Weir, the legendary Grateful Dead frontman.
Weir’s death has cast a strange pall over Deadheads like Cowan, who often wore clothes a Jerry Garcia t-shirt as a caddy for Tiger Woods. For those whose lives revolved around the rhythms of Grateful Dead concert schedules and retirement tours (plural), the band was more religion than music. And in the Church of the Dead, Weir was the heartbeat.
“In my mind, Bobby embodied the whole culture of the Dead, there’s kindness and there’s love,” said Gil Hanse, the golf course architect (and lifelong Deadhead). “Evidently [original Dead drummers Mickey Hart and Bill Kreutzmann] are still there, but it feels like the leader of the band has left the stage.”
Interestingly, Weir’s passing has also cast a strange pall over the US golf world, where the Dead have quietly infiltrated many of the sport’s highest chambers.
“The Dead has probably been the soundtrack to 70 percent of the holes I’ve formed and worked on in my career,” Hanse said. “So yeah, there’s a nice legacy there.”
Perhaps no one place appeals to both Deadheads And Golf enthusiasts really love the Bay Area. Pebble Beach is just an hour down the road from Dana Morgan’s Music Shop in Palo Alto, where Garcia and Weir first met as teenagers, and just two hours from Golden Gate Park, where Weir played his final three shows in the summer of 2025 (coincidentally just feet away from one of America’s most celebrated muni revival projects). Consciously or unconsciously, golf’s visit to the region this week has given the sport’s legion of Deadheads a chance to mourn.
Of course, there is a deep irony in Weir’s legacy stretching across the Monterey Peninsula’s most neatly manicured cliffs. Golf is a sport of well-coiffed boners and fetishized seclusion, the kind of place where even the appearance countercultural impulses can cost you a seat at some of the sport’s most renowned tables; In dead concerts there are people who openly question the timing of their last shower. (It should also be noted that if you were to design the diametric scientifically opposite from Shakedown Street – the popular Dead pre-concert tailgate, where sun-drenched roadies with surprising nonchalance trade tie-dye T-shirts and psychedelic drugs – you might end up with a place that looks a lot like 17 mile drive.)
And yet golf, like a particularly persistent case of lice, cannot rid itself of the Dead. A thriving underbelly of rejects and hippies floods the caddy yards and maintenance crews (and, in many cases, the membership lists) of America’s biggest clubs with Dead iconography; while golf’s own (gentle) countercultural moment of the 2020s has helped some clubs achieve this A touch of gray green side.
“I love them, need “Them, I can’t live without them,” said Cowan, capturing with impressive succinctness the spirit of dedication that caddy yards proclaim throughout the country.
From a distance the correlation may sound trivial, but spend time around golf’s true Deadhead contingent and you’ll realize that the sport and the band share a heartbeat. Despite golf’s occasional stuffiness, the sport’s best qualities can be taken verbatim from the central themes of a Dead concert: empathy, tranquility, creativity, artistry. And damn, is there a better place to do it? discover the wonders of nature than on a particularly psychedelic golf course?
“Everyone in our band, the Cavemen, we all have a role to play – and there’s some kind of foundation – but from that foundation we can take it in any direction we want,” says Hanse. “I think that’s kind of the ethos of the Dead. Every night was different in the way the music was performed and presented. We want creativity to manifest itself in improvisation.”
The core audience also helps. Many of the original Deadheads have since evolved into boomerdom, where golf is a national pastime, while many of the diehards responsible for keeping the sport going – those crazy enough to career in golf – I did this precisely because of the opportunity to break the shackles of a desk job and a nine-to-five job. For this group, The Dead is a siren song.
“I’ve often said that what we offer people is music with a little adventure in it,” Weir said in 2016. “The people who love our music, come to our music, are drawn to our music – they’re people who need a little adventure in their lives.”
Ultimately, the same adventurous spirit carried Weir to the end. He played his final shows with the Dead in Golden Gate Park in August – part of a celebration of the band’s 60th anniversary that drew more than 150,000 people to San Francisco. Hanse was among the crowd all three nights, having ‘got back on the bus’ with his wife Tracey in the last few years of Weir’s life. No one knew it at the time, but Weir waved goodbye.
“The first show was pretty rough, Bobby obviously wasn’t feeling well,” Hanse said, slipping into Deadhead lingo for a moment. “But Saturday and Sunday evenings were just… the magic.”
If an anti-establishment bent brought the Dead to golf, memories like these are what have kept them. Beneath the logos, the hippies and the music lies a spirit of something much greater: kindness.
“From the outside, people can draw whatever conclusion they want about golf, but… Real golfers find the same peace and tranquility when they are on the golf course,” Hanse said. “I mean, you had three nights with 50,000 people – and there were no crimes, no violence, nothing. Maybe some people were… chemically changed the way they felt, but they were there to celebrate something pure. And I think we celebrate the game of golf and the landscapes we play it in for the same reasons.”
For many Deadheads, this idea was the hardest part of Weir’s death. If the leader of the band was gone, what would stop the spirit of the Dead from leaving with him?
Fortunately, there are already signs that prove the opposite. One arrived on the morning of January 10, the same day news reached of Weir Hanse’s death on a golf course in New Zealand.
When Hanse faced an unexpected wave of grief, he had an unexpected visitor: his five-year-old granddaughter Peyton.
Peyton heard that her grandfather was upset and that she had taken matters into her own hands. She approached Hanse with a gift.
“She went outside and picked me some flowers from the meadow in the backyard,” Hanse said. “And she said, ‘I know you’re sad, so I just want to give you some flowers for your friend.'”
Hanse cried at the gift. He cried again and told the story.
They were tears of happiness. The kind that comes after an unusual act of kindness. His old friend Bobby would have liked that. He would have really enjoyed it.
But he would have liked it most what happened next, when Gil Hanse started his tractor and kept driving.
You can reach the author at james.colgan@golf.com.
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