The Entertaining Life of a Caddie: Interview with John Dunn

Caddie John Dunn has a multitude of fascinating stories to tell in his book. Courtesy: Pequot Library

Any person who follows golf knows that the relationship between a golfer and his caddie is, well, unique. Caddies are an integral and important part of any professional golfer’s game, and can be an invaluable resource.

Then, there are club caddies. Just as important, club caddies are people who love not only the game of golf, but the interactions they get to have with different people on a regular basis.

I recently had the opportunity to speak with one of these lovers of the game, named John Dunn, who authored the book Loopers: A Caddie’s Twenty-Year Golf Odyssey. In his 20 amazing years as a caddie, Mr. Dunn has carried the bags of, and given advice to the rich, famous, and powerful; and does he have some great stories to tell.

I caught up with Mr. Dunn on the phone and was able to find out a lot about his time as a caddie for such people as Kevin Costner, Bill Gates, and even about the time he caddied in the same group with Arnold Palmer.

But first I needed some clarification.

“What is the difference between a tour caddie, and a club caddie?”

"A tour caddie devotes their life to a single world-class player… a club caddie works for a club… There is a lot more personal freedom."

Tour caddies are almost like personal assistants to the player they caddie for, and everything they do is for the good of that player, whereas a club caddie gets the opportunity to caddie for all kinds of different people and has the opportunity to move around quite a bit, jumping from club to club.

However, that freedom to move from club to club comes at a bit of a price.

“I would guess with that freedom, and all the moving around you’re allowed to do, there is some sort of hierarchy and politics involved with club caddying?”

"That’s true, and there are disadvantages to being ‘new’ again every few years."

Starting at a new club, even with years of experience is like starting any new job. Your experience follows you onto the course, but in the clubhouse you’re still the “new guy”, which can be a disadvantage when it comes to the everyday tasks involved in caddying for a club.

“I’ve also noticed that caddies tend to caddie for a long time, even after it’s no longer in their best interests. Why do you think that is?”

"That’s a really tough question actually… It’s a great job, but it sort of ends up sucking in the end… But you don’t see that coming."

The problem with staying on as a caddie is, even though you’re having a great time and enjoying what you do, in the end you’re still a caddie. There isn’t much in the way of a promotional structure, or retirement plan. The problem is you’re having so much fun being around the game you love, you don’t realize that until it sneaks up on you.

"My friends that went and got ‘real jobs’ will call me and say, ‘Man, I wish I was still a caddie… I hate my job’ and I’m like, ‘Man I’m out on the links drinkin’ beer’, but now those guys have IRA’s and are making a hundred grand a year."

In his long career as a club caddie, Mr. Dunn has had the opportunity to caddie for some big names, both in Hollywood and the business world. Along with those experiences, come some really interesting and funny anecdotes that Mr. Dunn is more than willing to share.

“I understand you hijacked a beer cart while caddying for Kevin Costner?”

"I didn’t hijack the beer cart; I was put in it like an ambulance."

While golfing and celebrating the wrapping of his film, Tin Cup, Kevin Costner gave Mr. Dunn a Cuban cigar. Well, not really being much of a cigar smoker, Mr. Dunn found that the Cuban cigar was really strong.

"I turned green."

Not wanting anything to happen to him, Costner took Mr. Dunn quickly and carefully over to the beer cart, and had him sit in the cart until he felt better.

"I was the only caddie in the group and I was sitting in the beer cart drinking beer."

John also caddied for Bill Gates and during their round of golf, got a pretty unique opportunity.

"We went back and forth for like three hours about the Microsoft Anti-Trust lawsuit… And he defended his position passionately and eloquently like we were in a court room… It was amazing; I think I should have gotten college credit for it or something."

Apr 11, 2013; Augusta, GA, USA; Arnold Palmer hits a ceremonial tee shot before the first round of the 2013 The Masters golf tournament at Augusta National Golf Club. Mandatory Credit: Jack Gruber-USA TODAY Sports

When I asked what it was like to caddie for Arnold Palmer, Mr. Dunn quickly corrected me.

"I caddied in Arnold Palmer’s group… For his stepson."

Over three days, playing 36 holes a day he had what he called an “incredible” experience caddying in the same group as the man who is one of the greatest golfers of all time.

Not all of his run-ins with celebrities were fun however; one incident with actor Joe Pesci was actually pretty embarrassing.

While working at a very nice club near Los Angeles, Mr. Dunn was approached by a very tall, very attractive blonde woman. She got his attention and asked him to “tell Joe when he gets here, that I am here”.

Not hesitating, John immediately went to the valet and relayed the message, and was told that she meant Joe Pesci. When Mr. Pesci arrived John relayed the message to him:

"I say ‘Mr. Pesci your guest is here’ and he says ‘my guest?’, so I said ‘Your lady-friend?’, and he says ‘My lady-friend?’ I should have known after he repeated it the second time, but since I love the taste of my shoe in my mouth I tried again ‘Tall, attractive blonde?’ And he looked at me and said ‘ You should be a f***ing comedian, you know that?’… ‘That’s my wife, a**hole’… and even when he got back in the car he mumbled ‘where do they find these a**holes?’"

Obviously embarrassed, the other caddies didn’t make it any easier on him, but it served as a good ice breaker, since it happened on his first day as a caddie at that club.

John Dunn has innumerable stories and anecdotes after 20 years on the links as a club caddie, and more stories like these can be found in his book, Loopers: A Caddie’s Twenty-Year Golf Odyssey. The book is 12 chapters, written in chronological order, and each chapter is about his experiences at a different club.

Loopers: A Caddie’s Twenty-Year Golf Odyssey hit the shelves on May 14, 2013 and is available from Crown Publishing.