Feb. 13, 2026Updated Feb. 15, 2026, 8:36 a.m. ET
PEBBLE BEACH, Calif. – Why is 11-time National Sportswriter of the Year Rick Reilly on the bag of a billionaire sports owner at the 2026 Pebble Beach Pro-Am?
Reilly, 68, a New York Times best-selling author and best-known for his back-page column in Sports Illustrated, is working on a sequel to his 2003 hit “Who’s Your Caddy?” In that book, he recounts his experiences caddying for famous golfers and celebrities and offers a funny and revealing look at the world of golf. In the original collection, he lugged the bags for everyone from Donald Trump to the blind world golf champion. He’s at it again.
Reilly’s on the bag for Ryan Smith, a co-founder of Qualtrics, a cloud-based software company that he sold for billions. Smith has since invested in sports franchises, becoming the owner of the NBA’s Utah Jazz and NHL’s Utah Mammoth in his home state. He’s also a devoted golfer, who played in the DP World Tour’s Alfred Dunhill Links Championship in Scotland in September. and he’s close friends with six-time PGA Tour winner Tony Finau. The duo is paired together this week at the AT&T Pebble Beach Pro-Am and Reilly swung the gig as his caddie for a chapter in the book scheduled to be released for Father’s Day in 2027.
Reilly didn’t have it too bad – Smith was using a light, kickstand bag at Spyglass and Pebble Beach. Reilly knows the deal from past experience as a caddie – show up, keep up, shut up – and promised he’d do better on Friday during the second and final round of the 36-hole pro-am. Smith dismissed the notion. “Don’t change a thing tomorrow,” he said.
Those are words any caddie would love to hear. But ultimately, the final proof of how well he does comes down to the tip at the end of the week. How much does a billionaire give for a little effort?
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Said Reilly: “I’ll settle for a ride in his jet!”
