A Viral Caddie’s Rise and the New Shape of Golf Culture

In a new Dan's Golf World Show, a caddie-turned-content creator joins to offer fresh perspective on the new landscape for golf content creators.

Episode 48 of the Dan's Golf World Show. / Dan Evans

After one of the most dramatic finishes of the season at the Travelers Championship, golf fans were left split—heartbroken for Tommy Fleetwood or stunned by Keegan Bradley’s clutch win. On this week’s Dan’s Golf World Show, the team dissected a final hole that flipped everything: Fleetwood’s bogey, Bradley’s birdie, and a subtle ridge in the green now dubbed “Speed Bump Gate.”

But the bigger story might be what happened off the leaderboard. Joining the show was Gerry Carry, a caddie-turned-content creator whose blue-collar wisdom and viral videos have made him a cult figure in modern golf. From walking Oakmont at sunrise to caddying in high-profile junior matches, Carry’s influence is built not on swing mechanics, but on mindset and presence. “A real caddie keeps your head between the ditches,” he told the crew. “That’s the job.”

His rise says something about where the game is heading: toward access, authenticity, and a broader cultural footprint. Carry’s not a PGA Tour veteran—but he’s earned the trust of players, fans, brands and juniors alike, all while working out of a carry bag and an iPhone.

In a sport still wrestling with tradition and transformation, this week’s episode captured both ends of the spectrum—gutted pros at the top of the leaderboard, and a new kind of golf voice walking somewhere just outside the ropes.

Watch the full episode of Dan’s Golf World Show above and check out more episodes on SI Golf.