At Pebble Beach, golf calls out to a legend from another world

PEBBLE BEACH, Calif. – Eighteen months ago, on a beautiful Sunday evening at the President’s Cup in Montreal, Fluff Cowan’s mustache curled.

“Oh, I don’t know,” said the legendary singer, his New England accent masking the nervousness behind the snow-white facial hair.

He paused, turning the thought over in his head. He’s been asked some strange questions in his 47 years as one of the greatest players in golf history, but none quite like this one.

How can he capture all of his caddying experience … in one song?

“Well, I think the first one that comes to mind is – in the ways it ebbs and flows…”

He paused again, in pain.

“I guess I’ll have to go with “Truckin’,” he said.

The conversation continued, but Cowan seemed to linger on the subject, happy with his choice. It took his spirit, his story, and critically, his favorite band: The Grateful Dead. After a few strokes, his face softened and became patient.

“I was just driving a fool.“

Cowan turned 78 on Saturday, two days before the start of a golf tournament that has once again felt like the start of a new year: the annual AT&T Pebble Beach Pro-Am. But the start of this peak golf season in Northern California has lost its 2026 shine. In early January, the world learned of the passing of one of Cowan’s heroes: Bob Weir, the Grateful Dead frontman.

Weir’s death has saddened Deadheads like Cowan, who used to wear a Jerry Garcia T-shirt to caddy for Tiger Woods. For those whose lives revolved around the rhythm of Grateful Dead concert shows and retirement tours (plural), the band was more religion than music. And in the church of the dead, Weir had a beating heart.

“In my mind, Bobby embodies the whole culture of the dead, there’s kindness and love,” says Gil Hanse, golf course architect (and lifelong Deadhead). “It’s obvious [original Dead drummers Mickey Hart and Bill Kreutzmann] they are still there, but it sounds like the leader of the group has left the stage.”

Interestingly, Weir’s passing also hit him hard golf in the world, where the Dead have sneaked into many of the highest sports halls.

“The dead were about 70 percent of the sound of the holes I dug and worked on in my career,” Hanse said. “So, there’s a good legacy there.”

Perhaps there is no place that speaks to both dead again golf lovers 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 is playing his last three shows in the summer of 2025 (probably just meters from one of the most prestigious muni revitalization projects in America). Consciously or unknowingly, golf’s tour of the region this week has given the Deadheads’ legion of sportsmen a chance to mourn.

“I’ve always felt bad about it,” said Hanse. “I didn’t expect that. It was more difficult than I thought.”

Of course, there is a deep irony in Weir’s legacy that extends over the Monterey Peninsula’s perfectly manicured cliffs. Golf is a game of well-rounded intensity and modified contact, the kind of place where I say appearance going against the rules can cost you a seat at some prestigious sports tables; Dead concerts include the kind of people who ask open-ended questions about their last bath. (It should also be noted that if you were a diametric engineer the opposite (of Shakedown Street — the famous Dead pre-concert tailgate where sun-kissed streetwalkers trade tie-dye T-shirts and psychedelic drugs with surprising nonchalance — you might find the place almost identical to 17 Mile Drive.)

And yet, like a particularly stubborn case of lice, golf cannot eradicate the Dead. Prosperity under abandonment and hippies flood the caddy yards and maintenance staff (and, in many cases, the membership rolls) of America’s biggest clubs with the image of a dead icon; while golf’s (mild) countercultural moment of the 2020s helped some clubs bring Touch of Gray green.

“Love them, the need ’em, I can’t live without them,” said Cowan, capturing the air of devotion that heralds caddy yards across the country with astonishing brevity.

From a distance, the connection may sound trivial, but spend time around a real Deadhead golfer and you’ll see the game and the band share a heartbeat. For all of golf’s occasional focus, the best aspects of the sport may be taken verbatim from the central themes of the dead concert: compassion, peace, art, creativity. And, hell, is there a better place discover the wonders of nature is there a particularly psychedelic golf course?

“Everybody in our group, the Cavemen, we all have a role to play – and there’s a kind of foundation – but when we get out of that foundation, we can take it in any direction we want to,” Hanse said. “I think that’s kind of the ethos of the Dead. Every night was different in the way the music was played and presented. We want the art to be reflected in the improv.”

The main audience also helps. Many of the original Deadheads have now aged into boomerdom, where golf is the national pastime, while many of the diehards are responsible for keeping the game going – those who are demented enough to pursue the game. work in golf – they did precisely that for a chance to break the chains of the desk job and the nine-to-five. For this group, the Dead are the siren song.

“I’ve always said that we provide people with music that has a bit of a journey to it,” Weir said in 2016. “People who like our music, who come to our music, are attracted to our music — they are people who need a little adventure in their lives.”

In the end, the same spirit of self-sacrifice carried Weir to the end. He played his last shows with the Dead at Golden Gate Park in August – part of the band’s 60th anniversary celebration that drew more than 150,000 people to San Francisco. Hanse was in the crowd for three nights, “jumping on the bus” with his wife, Tracey, for the last few years of Weir’s life. No one knew it at the time, but Weir was waving goodbye.

“The first show wasn’t easy, Bobby obviously wasn’t well,” Hanse said, slipping briefly into the Deadhead vernacular. “But on Saturday and Sunday night it was just… magic.”

If the anti-establishment bent on bringing the Dead to golf, memories like these are what saved them. Beneath the logos and the hippies and the music is the spirit of something much greater: kindness.

“Outside, people can reach whatever conclusions they want with golf, but the original golfers find the same peace and quiet when they are off the golf course,” said Hanse. Maybe some people were… chemically modified how they felt, but they were there to celebrate something pure. And I think we celebrate the game of golf and the places we play for the same reasons.”

For many Deadheads, this idea was the hardest part of Weir’s death. If the leader of the group is gone, what would stop the spirit of the dead from passing with him?

Thankfully, there are already signs of that. Another arrived on the morning of January 10, the same day news of Weir’s passing reached Hanse on the golf course in New Zealand.

As Hanse finds himself dealing with an unexpected surge of grief, he receives an unexpected visitor: His five-year-old granddaughter, Peyton.

Peyton sensed that her grandfather was upset, and she was holding herself back. He approached Hanse with a gift.

“He went outside and picked flowers for me from the backyard,” said Hanse. “And he said, ‘I know you’re sad, so I want to give you flowers for your friend.'”

Hanse cried when he saw the gift. He cried again while telling the story.

They shed tears of joy. The kind that comes after an unusual act of kindness. His old friend Bobby would have liked that. He would have loved it so much.

But he would like to the majority what followed after that, when Gil Hanse shot his tractor, and continued to ride the truck.

You can reach the author at james.colgan@golf.com.