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 at Sports Illustrated to caddy for some of the world’s most famous golfers—and some celebrity duffers—with hilarious results.

Who knows golfers 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 games 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, Casey Martin, and Jill McGill—agreed to let Reilly carry their bags at actual PGA and LPGA Tour events. Reilly also caddied at the Masters, persuaded Deepak Chopra and Donald Trump to use him as a caddy, accompanied high-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.
To really know someone, as the saying goes, you must walk a mile in their shoes. But to really understand a golfer, you’ve got to work as their caddy. Sports Illustrated columnist Rick Reilly managed to get some very intriguing golfers to let him lug their bag and write what he learned both about the game and the folks who play it. Going hole to hole with them let Reilly know a different side of veterans such as John Daly, David Duval, Tom Lehman, and Jack Nicklaus. But Reilly also went beyond the pros to caddy for Deepak Chopra, Donald Trump, professional gambler Dewey Tomko, and Bob Newhart. In some cases, the portraits that emerge fall directly in line with the popular image but at other times it’s just the opposite. Daly is sober but has shifted his addiction to massive amounts of Diet Coke, candy, and marriages; Duval is intensely driven during rounds but surprisingly laid back and friendly off the course; Chopra’s inner peace is locked in a mortal battle with the inherent frustrations of golf; and Trump manages to be both an egomaniac and a pretty nice fellow. And although he’s on assignment to profile his temporary employers, Reilly emerges as an entertaining figure in his own right as he commits numerous faux pas, breaks taboos, infuriates multiple golfers and caddies, accidentally dumps all of Nicklaus’s clubs onto the turf in the middle of a round, and discovers that caddying is tougher than it looks. Reilly walks a nice line with the tone of Who’s Your Caddy?: it’s reverent to the game without becoming a misty-eyed poetic ode, and it’s laugh-out-loud funny without being nasty or low brow. And while golf fans will certainly appreciate it, Who’s Your Caddy? is an impressive book for fans of biography in general. –John Moe
[amz_corss_sell asin=”0739333445″]