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Who's Your Caddy?: Looping for the Great, Near Great, and Reprobates of Golf
The funniest and most popular sportswriter in America abandons his desk to caddy for some of the world’s most famous golfers—and some celebrity duffers—with hilarious results in this New York Times bestseller.
Who knows a golfer best? Who’s with them every minute of every round, hears their muttering, knows whether they cheat? Their caddies, of course. So sportswriter Rick Reilly figured that he could learn a lot about the players and their game by caddying, even though he had absolutely no idea how to do it. Amazingly, some of the best golfers in the world—including Jack Nicklaus, David Duval, Tom Lehman, John Daly, Jill McGill of the LPGA tour, and Casey Martin—agreed to let Reilly carry their bags at actual PGA and LPGA Tour events. To round out his portrait of the golfing life, Reilly also persuaded Deepak Chopra and Donald Trump to take him on as a caddy, accompanied the four highest-rolling golf hustlers in Las Vegas around the course, and carried the bag for a blind golfer.
Between his hilarious descriptions of his own ineptitude as a caddy and his insight into what makes the greats of golf so great, Reilly’s wicked wit and an expert’s eye provide readers with the next best thing to a great round of golf.
Who knows a golfer best? Who’s with them every minute of every round, hears their muttering, knows whether they cheat? Their caddies, of course. So sportswriter Rick Reilly figured that he could learn a lot about the players and their game by caddying, even though he had absolutely no idea how to do it. Amazingly, some of the best golfers in the world—including Jack Nicklaus, David Duval, Tom Lehman, John Daly, Jill McGill of the LPGA tour, and Casey Martin—agreed to let Reilly carry their bags at actual PGA and LPGA Tour events. To round out his portrait of the golfing life, Reilly also persuaded Deepak Chopra and Donald Trump to take him on as a caddy, accompanied the four highest-rolling golf hustlers in Las Vegas around the course, and carried the bag for a blind golfer.
Between his hilarious descriptions of his own ineptitude as a caddy and his insight into what makes the greats of golf so great, Reilly’s wicked wit and an expert’s eye provide readers with the next best thing to a great round of golf.
261 pages, Paperback
First published January 1, 2003
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Displaying 1 - 30 of 153 reviews
June 10, 2025
WHO'S YOUR CADDY sets the standard for golf humor and it is hilarious. Each chapter features award winning sportswriter Rick Reilly’s experience caddying for a different celebrity. Some in golf and some not.
If you don't have time to read the entire book, then you owe it to yourself to read the chapter describing Reilly's day looping for Donald Trump. On that day, Trump mostly did not play his first ball, and then lied about it. A grown man lying brazenly about such a trivial thing seemed nuts. And Trump comes off as weak and ridiculous. Of course, back then Trump was a private citizen and not meant to be taken seriously, So we can shake our heads and laugh it off.
But now, Reilly’s description of Trump on that occasion long ago is unsettling. Now, it confirms our worst fears about current events, such as the Alabama hurricane incident this past week (and numerous others) where Trump is plainly and shamefully caught lying.
We are not imagining it. Reilly’s story from twenty-five years ago eliminates any doubt that Trump is off his gourd.
If you don't have time to read the entire book, then you owe it to yourself to read the chapter describing Reilly's day looping for Donald Trump. On that day, Trump mostly did not play his first ball, and then lied about it. A grown man lying brazenly about such a trivial thing seemed nuts. And Trump comes off as weak and ridiculous. Of course, back then Trump was a private citizen and not meant to be taken seriously, So we can shake our heads and laugh it off.
But now, Reilly’s description of Trump on that occasion long ago is unsettling. Now, it confirms our worst fears about current events, such as the Alabama hurricane incident this past week (and numerous others) where Trump is plainly and shamefully caught lying.
We are not imagining it. Reilly’s story from twenty-five years ago eliminates any doubt that Trump is off his gourd.
June 6, 2009
Reilly is funny, and the sections of this book where he caddies at the Masters, for John Daly, Donald Trump, Jack Nicklaus, and Deepak Chopra are excellent. His other trips with PGA tour pros are good too. He must be doing something right: he made me feel like watching a golf tournament, or following the PGA which I haven't done since I sold my own clubs after years of terrible driving spoiled the game for me.
He's a little bit less effective when he's trying to be inspirational. For me, the last chapter with the blind golfer falls flat, feels cliched. Reilly loses a star for the way he handles his time with LPGA pro Jill McGill. It's sexist, plain and simple. Suddenly all he has to talk about are periods, who looks good, who's a lesbian, what clothes they wear, and whether or not men can drive further.
But overall it's a very funny and often insightful book. Just skip the chapter on McGill.
He's a little bit less effective when he's trying to be inspirational. For me, the last chapter with the blind golfer falls flat, feels cliched. Reilly loses a star for the way he handles his time with LPGA pro Jill McGill. It's sexist, plain and simple. Suddenly all he has to talk about are periods, who looks good, who's a lesbian, what clothes they wear, and whether or not men can drive further.
But overall it's a very funny and often insightful book. Just skip the chapter on McGill.
April 14, 2014
cc:
Who knows a golfer best? Who's with them every minute of every round, hears their muttering, knows whether they cheat? Their caddies, of course. So sportswriter Rick Reilly figured that he could learn alot about the players and their game by caddying, even though he had absolutely no idea how to do it. Amazingly, some of the best golfers in the world-including Jack Nicklaus, David Duval, Tom Lehman, John Daly, Jill McGill of the LPGA tour, and Casey Martin-agreed to let Reilly carry their bags at actual PGA and LPGA Tour events. To round out his portrait of the golfing life, Reilly also persuaded Deepak Chopra andDonald Trump to take him on as a caddy, accompanied the four highest-rolling golf hustlers in Las Vegas around the course, and carried the bag for a blind golfer.
In the same inimitable style that makeshis back-page column for "Sports Illustrated "a must-read for more than fifteen million people every week, Reilly combines a wicked wit with an expert's eye in the most original and entertaininglook at golf ever.
by Rick Reilly
Who knows a golfer best? Who's with them every minute of every round, hears their muttering, knows whether they cheat? Their caddies, of course. So sportswriter Rick Reilly figured that he could learn alot about the players and their game by caddying, even though he had absolutely no idea how to do it. Amazingly, some of the best golfers in the world-including Jack Nicklaus, David Duval, Tom Lehman, John Daly, Jill McGill of the LPGA tour, and Casey Martin-agreed to let Reilly carry their bags at actual PGA and LPGA Tour events. To round out his portrait of the golfing life, Reilly also persuaded Deepak Chopra andDonald Trump to take him on as a caddy, accompanied the four highest-rolling golf hustlers in Las Vegas around the course, and carried the bag for a blind golfer.
In the same inimitable style that makeshis back-page column for "Sports Illustrated "a must-read for more than fifteen million people every week, Reilly combines a wicked wit with an expert's eye in the most original and entertaininglook at golf ever.
by Rick Reilly
March 11, 2021
Who's Your Caddy is a great book to read if you want to know what it is like to be a caddy. This book is about a famous author that quits his job to then go caddy for famous people. While he is on the golf course with him he writes different sections of the book about what they are like and just a general description of their personality. This book helps picture what celebrities are like in their own lives not in the eyes of the media. When he was caddying for people on the PGA tour it was really interesting to hear what they think about throughout a round of golf and as a golfer it really is intriguing hearing what the players have to say. This book is defiantly very intriguing for golfers but if you are not fond of the game I would still recommend this book for you. In the media you see all these people in their professional life more than ever right now so it is very interesting to see how they act not in the spotlight.
September 21, 2010
I started reading Rick's weekly stories in the back of SI when my ex would get the magazine. And since I laughed so much week to week, when I found this book, I had to try it. And it did not disappoint.
Someone being totally honest, and comical, about some of the big names on the PGA and LPGA is great. In most of the situations in the stories, most of us would have walked/run away and never looked back. Rick, however, takes the sour and sometimes happy incidents and makes them amusing for those of us that could never get anywhere near Augusta as a caddy.
Someone being totally honest, and comical, about some of the big names on the PGA and LPGA is great. In most of the situations in the stories, most of us would have walked/run away and never looked back. Rick, however, takes the sour and sometimes happy incidents and makes them amusing for those of us that could never get anywhere near Augusta as a caddy.
December 3, 2014
This might actually pass the Bechdel Test, in the one chapter devoted to the LPGA. There might be some conversations between women there, about golf and lesbianism / perceptions of lesbianism.
Sometimes I like to read golf books, in memory of my Dad. Whose book this was, and who probably didn't enjoy it that much because it's pretty crass. I probably should have considered the cover on this one, but it gave me my annual golf lingo fix, so okay.
Sometimes I like to read golf books, in memory of my Dad. Whose book this was, and who probably didn't enjoy it that much because it's pretty crass. I probably should have considered the cover on this one, but it gave me my annual golf lingo fix, so okay.
March 24, 2020
The book, Who’s Your Caddy, by Rick Reilly, talks about a guy who went and caddied all around the country to walk alongside with some of the greatest golfers and people in the world. The book is a very good book as it gives insight at some of the greatest golfers actions during their golf rounds out on the course. I really enjoyed reading this book because I love golf and it talks about golf and some of my favorite golfers throughout the book. I love being able to read stories on how John Daly acts without all the cameras in his face and how he is just out there living his best life. The book was able to show me many new interesting facts about some people like how Donald Trump actually has a pretty good golf handicap even though he might cheat here and there on his score, but since he is Donald Trump so no one will tell him what to do. My favorite part of the book would be the chapter when he caddies for John Daly. Daly is one of my favorite golfers to watch on the PGA Tour because of the way he dresses and acts while playing golf. Being able to just learn more stories about him just makes me be even more of a fan of his. The book had very few parts of the book that were tough to read, but there were a couple times where I became a little confused while reading. The book was really well written and I could not put up a debate at some parts during the book that could put this book down. I would recommend this book to any true golfing fan out there because it talks about being a caddy for some of the greatest golfers of all time and gives you stories you never heard of about even the Golden Bear, Jack Nicklaus. The book was an amazing book and well written and I would give it a nine out of ten.
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November 7, 2019 Growing up watching players like Tiger Woods and Jordan Spieth, I have always wondered what they say to their caddies. Caddies are play a major role on the course and off the course. They are the ones who help players win tournaments and they are also the ones getting drinks after the round with the players.
Who’s Your Caddy by Rick Reilly provides great insight into the relationship between caddies and golfers. Rick Reilly left his job as a sports writer to become a caddy. He caddied for players of all ranges of skill level. Rick Reilly caddied for famous weekend players like Donald Trump and Deepak Chopra, and tour players like John Daly and Jack Nickalaus. Reilly mainly focuses on the funny aspects of his time as a caddy, but this is still a major portion of the relationship between caddies and players. The general public would be oblivious to these stories without Reilly’s book.
I really enjoyed reading this book, because it is a side of golf not really seen by the viewer. I am only able to view the “in the zone” version of the players and I don’t really get to see who they are outside of tournaments. Even though I was reading someone else’s stories, I feel like gained a better understanding for the players and who they really are. I highly recommend reading this book.
Who’s Your Caddy by Rick Reilly provides great insight into the relationship between caddies and golfers. Rick Reilly left his job as a sports writer to become a caddy. He caddied for players of all ranges of skill level. Rick Reilly caddied for famous weekend players like Donald Trump and Deepak Chopra, and tour players like John Daly and Jack Nickalaus. Reilly mainly focuses on the funny aspects of his time as a caddy, but this is still a major portion of the relationship between caddies and players. The general public would be oblivious to these stories without Reilly’s book.
I really enjoyed reading this book, because it is a side of golf not really seen by the viewer. I am only able to view the “in the zone” version of the players and I don’t really get to see who they are outside of tournaments. Even though I was reading someone else’s stories, I feel like gained a better understanding for the players and who they really are. I highly recommend reading this book.
February 17, 2019
I was in the mood to read something humorous and light after finishing a heavier read, and this book was a great choice. (Plus it got me that much more excited for this Ohio weather to finally change so I can get out there and golf!!) I read this at the reccomendation of my husband. He said it would have me laughing out loud and even learn a bit about the great game. He was right, even if the book was a little crass.
Chapter by chapter, Reilly tells the hilarious account of him caddying for various golfers. The hardest thing about reading this book was stomaching the chapter on Reilly caddying for Trump; what a piece of work. The best part was reading about Casey Martin and Bob Andrews; how good of guys are they!? This was a fun book to read.
Chapter by chapter, Reilly tells the hilarious account of him caddying for various golfers. The hardest thing about reading this book was stomaching the chapter on Reilly caddying for Trump; what a piece of work. The best part was reading about Casey Martin and Bob Andrews; how good of guys are they!? This was a fun book to read.
June 14, 2018
I am not a golfer. But I generally enjoy anecdotal insights into realms of living that are foreign to me. This book has a lot of golf lingo, but it is still understandable from a layman's point of view. A lot of different personalities are presented, and you do get a feel and appreciation for the game of golf. The author does not write about women well though, seeing them only through the lens of sexual objectification, and you get the impression that golf is (or should be) a game for the 'good ol' boys' only.
August 7, 2023
Super interesting and makes me miss Reilly on the back page of Sports Illustrated. The stories he chose to fill out the book are funny, interesting, and each one doesn't overstay its welcome. That said the book was probably one or two chapters too long as I found myself really dragging to the finish line. If you like Reilly's style it's a must read, if you want to learn more about golf as a culture it's a must read.
April 15, 2025
I give "Who's Your Caddy" 5 stars. This book does a great job going in depth with Rick's relationships with celebrities and professional golfers. Rick does a great job telling his stories of inside the ropes with all of his players. He explains the finical sides of being a caddy and a player. I would recommend this book to anybody who loves the game of golf and loves jokes. This book had a lot of funny moments and scenes that he talked about.
July 8, 2021
Just recently fell in love with golf, and have been looking to consume some reading material on the game. I enjoy reading instructional literature on the game, but also enjoy reading some books “about” golf; The history, fun stories, etc. This book was recommended to me by some friends, and overall, I really enjoyed it. I loved the different perspectives on the game, the stories about and from some celebrities, including Trump. The writing style left a little to be desired - very casual - but easy to read. Some of the jokes have not aged well at all, and I winced at a few of them for being in poor taste by today’s standards. Overall, though, I really enjoyed the read, and look forward to reading his newer book on golf and Trump.
January 23, 2023
Ghastly. NONE of it was funny, though the author and his friends tried hard. And the language along with dirty jokes was a total turn-off. I wish I could give the book NO stars. And I embarrassed to say I even made an attempt at reading it. Obviously it was a slow day at the used book store when I chose it.
May 17, 2017
Typical Rick Reilly, very funny as he puts the reader on the golf course as a caddy. As an avid golfer, I found the situations funny and not unusual. I wish he had caddied for an additional ten or more golfers.
July 9, 2017
I'm not a golfer (yet) but my boyfriend let me borrow the book. It was hysterical! I obviously have quite a lot to learn about golfing and looping that I can't learn just by watching on TV. For a non-golfer, this was a very funny read..
August 24, 2017
The author asked a few pro golfers and celebrities if he could caddy for them. This tells us a bit about the people, their personalities and their golf. A very funny read and gives a great insight into what these people are like.
May 31, 2019
Good stories about a variety of golfers and famous people... dated... should have set up the chapters better... narration was good and writing was good.... i would read him again... he covers golf and human interest stories in his writings about 12 people
June 8, 2020
Decent read if you are or are not a golf fan. Particularly disturbing is Rick's account of TOTUS (President Trump) when he caddy's for him in 2003: cheater, boaster, liar, etc. Somethings and some people never change.
June 30, 2021
This was great fun!
Rick Reilly, a Sports Illustrated writer, persuades some famous people, pro-golfers & celebrities, to let him caddy for them.
You learn a great deal about the people along the way & there are lots of amusing anecdotes.
A great red whether you are a golfer or not!
Rick Reilly, a Sports Illustrated writer, persuades some famous people, pro-golfers & celebrities, to let him caddy for them.
You learn a great deal about the people along the way & there are lots of amusing anecdotes.
A great red whether you are a golfer or not!
January 14, 2023
beautiful book on golf
I highly recommend this book for its humor, for its humanity, and for its insightful stories. The author is a genius and I will keep on my quest to read every book he has written.
I highly recommend this book for its humor, for its humanity, and for its insightful stories. The author is a genius and I will keep on my quest to read every book he has written.
March 16, 2025
This book is fantastic - I think even if you’re not a golfer. All the chapters are unique, and insightful, but the last chapter will possibly have you appreciating your life as much as ever. BTW - it as funny as it is insightful.
December 19, 2017
In one chapter he caddies for Trump.
December 22, 2017
This book will drive you to read it and well worth your time.
January 8, 2018
An entertaining read.
May 6, 2018
Easy read with some funny stories. Made we want to play some golf!
June 7, 2018
Perfectly hilarious
August 19, 2018
So funny. No golf experience needed.
October 23, 2018
bloody brilliant - please write a followup Rick
November 22, 2018
I did the audio book on CD’s. Very clever writing. Thoroughly enjoyed it. Time for Who’s Your Caddy II ! Maybe Tiger will say yes this time. Haha
Displaying 1 - 30 of 153 reviews