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Yes, I’m obsessed with golf. And yes, I’m obsessed with books. You’d think I’d have read all the best golf books by now. But here I am just getting to Rick Reilly’s Who’s Your Caddy book in 2025. Some 20+ years after it was first published (2003.) Does it still hold up as the preeminent golf humor book written by a Sports Illustrated columnist? (Well, Reilly did write a couple others, so there is some competition.)
Inside, I found John Daly, Bob Newhart, Jack Nicklaus. And oh yeah, a certain guy named Trump, back when he was just a golf-obsessed mogul instead of, you know, President.
My Who’s Your Caddy Book Review:
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Table of Contents
Who’s Your Caddy Book Summary
Full Title: Who’s Your Caddy? Looping for the Great, Near Great, and Reprobates of Golf
Rick Reilly’s Who’s Your Caddy isn’t just a golf book. It’s a backstage pass to some of the strangest, funniest, and most ego-filled walks in golf history (at least up until 2003.) Reilly was a sportswriter with a sharp wit and sharp tongue. He convinces famous golfers, celebrities, and moguls to let him caddy for a round. His opportunities lead to inside-the-ropes reporting mixed with stand-up routine.
Among the highlights: Reilly loops for Jack Nicklaus, trying to soak up wisdom from the Golden Bear while not tripping over himself in awe. He carries the bag for John Daly, golf’s ultimate cult hero, where the experience is as chaotic and unpredictable as Daly’s drives off the tee. And then there’s Donald Trump (long before he was President.) Already larger than life, obsessed with his golf empire, and providing enough material for a full comedy set.
Note – Rick Reilly’s book is NOT related to the 2007 movie with the same name, which has a 6% rating on Rotten Tomatoes (not good.)
Golfers Who Rick Reilly Caddied for:
Here are the celebs, profesionals and plain ol interesting characters Reilly caddied for in the book:
- Tommy Aaron – 1973 Masters champ.
- John Daly – golf’s patron saint of chaos (and long drives.)
- Donald Trump – pre-politics, still golf-obsessed.
- Tom Lehman – Minnesota nice on the course.
- David Duval – a top player of the era.
- Dewey Tomko – world’s most notorious golf gambler.
- Jack Nicklaus – the Golden Bear himself.
- Deepak Chopra – the spiritual detour chapter.
- Casey Martin – inspirational story, golfing with a disability.
- Bob Newhart – the surprisingly golf-obsessed comedian.
- Jill McGill – the lone woman featured.
- Bob Andrews – a remarkable amateur story of a blind golfer.
Who is Rick Reilly?
Rick Reilly is a longtime sportswriter best known for his witty, sarcastic columns at Sports Illustrated and later ESPN. Over his career, he’s written more than a dozen books, many of them sports humor, including this one, which might be his most famous. If you were a sports fan in the ’90s or early 2000s, chances are you read him whether you meant to or not. He was a pretty big deal in the sports journalism world.
Find Reilly’s SI article archive here: Articles by Rick Reilly – Sports Illustrated Vault | SI.com
Want some more golf books? Check out these ones!
Now onto the rating! Reilly’s Who’s Your Caddy Book Review:
My innovative system for rating humor books is explained here
Wholesomeness Score: 3/5
Not terribly wholesome, but not a complete moral disaster either. Coarse language and crude content throughout (like when John Daly apparently exposed himself.) But also had wholesome and inspirational good guys like Casey Martin giving the warm fuzzies about perseverance and life.
Hilarity Score: 5/5
Rick Reilly made a career out of mixing humor with sports stories. some laughs come straight from the eccentric characters he caddied for, but he doesn’t just rely on them. Reilly knows how to find the funny in every bunker, fairway, and awkward interaction.
Overall Book Awesomeness Score: 4/5
Loved the concept. Reilly caddying for golf’s biggest personalities is equally wild and entertaining. Honestly, I’d rather tee it up with these famous (and infamous) players myself, but hauling their bags makes for a pretty great next-best option.
Things I liked:
- Inside scoop on golf legends. Reilly gets up close with both pros and amateurs, giving readers a peek behind the curtain. Many of these names are still famous (some even more so) two decades later.
- Reilly finds the funny
Things I didn’t like:
- Token woman alert. The book features only one woman, Jill McGill. Reilly spends most of the chapter circling around sex appeal, menstrual cycles, and other clichés. Not exactly a modern portrait of women in sports, but this was 2003. Comes off a bit cringy today.
Conclusion: Who’s Your Caddy Book Review
So here I am in 2025, finally reading Rick Reilly’s Who’s Your Caddy. As a golf fan, a book nerd, and someone who read Reilly in my younger years, I’m glad I picked this one up. The premise is straightforward but brilliant: Reilly caddies for golf legends, celebrities, and random moguls, then writes about what actually happens inside the ropes.
Jack Nicklaus brings the gravitas, John Daly brings the chaos, and Donald Trump (long before politics) is the same golf-obsessed showman he’s always been. What makes the book work is Reilly’s access and his ability to pull humor out of every situation. For golf fans, it’s a fun behind-the-scenes look. For comedy fans, the laughs still hold up.
Read it? Loved it? Hated it? Caddied for anyone famous? Let me know in the comments.
