First Person

Undercover Caddie: A longtime resort looper's friendly advice for all golfers

December 03, 2021

I've been a caddie for nearly 20 years, with stints at some of the world’s best resorts. Although I’m not big on soapboxing, a lot of you could use some friendly advice. Before I tell you what you get wrong, let me start by telling you what you get right: You tip well. You’re generous about asking if I’d like a dog and a drink at the turn. It’s impossible to count how many players, many of whom I had for just 18 holes, send me cards and gifts during the holidays. Overall, you’re a good group, but you lack self-awareness. Here are some things to work on:

You’re too slow. Perhaps not too surprising but it seems like half of my job is prodding a group like sheep to play ready golf. I don’t like being the time-cop enforcer because when people feel rushed, the tips aren’t as generous. But please stop standing around and watching your playing partners. Take a practice swing, read from one angle and get on with it.

You talk about yourself— a lot. I did two seasons in Ireland (one at Ballybunion), and, man, the caddies there dig Americans. But, as one told me, Yankee golfers struggle with vanity. You endlessly talk about your golf game without complimenting your playing partners. Same goes for discussions about business, family, politics and sports. There’s little group discourse or listening, just four individuals waiting for someone else to stop talking so they can talk. (One time a woman said she was going through a divorce, and her competitor nodded and said, “For the life of me, I can’t keep this 5-iron out of the wind.”) Golf is an individual game, but if you let it, it can be a communal experience.

‘I can tell within two shots if you’re a player or a hacker.’

You have the emotional intelligence of a puppy. I spent a quarter of my career at Pebble Beach, a place golfers spend their lives dreaming of visiting. You’d think it would be four hours of walking on rainbows. Instead, you base your enjoyment on the shot you just hit or the hole you just finished. I get it. No one wants to back up the Brinks for a tee time and play like crap. But you’re not a pro. Try to hit a few good shots, and if that doesn’t happen, so what? You’re playing golf; life is good. That goes for a round at a bucket-list venue or your Tuesday night work league.

Stop apologizing—and lying. “I’m so sorry” or “I’m normally not this bad.” I hear a variation of this about three times a week after a player has made consecutive bogeys. I appreciate where you’re coming from, but I’ve seen bad, brother. I want you to play well, and I’ll do my best to help you, but I don’t care what you shoot. Just try to have a good experience. Besides, I can tell within two shots if you’re a player or a hacker, and 95 percent of the time, the apologies are coming from a hacker.

You don’t prepare for bad weather. The hardest items to keep stocked in our golf shop are rainsuits and sweaters. If you think those pieces are expensive online, you have no idea about the bill coming your way at a resort golf shop. A lot of prime courses are on or by the water, so expect three seasons in one day. Also, even if you’re playing at your home course, you should have rain gear in the bag.

You don’t know how far you hit your irons. For every ball that goes long, 30 fall short. If I say 150 yards, and your response is 8-iron, stop and think: Is that how far my 8-iron usually goes or just when I catch all of it? Most golfers let the latter dictate the shot when it should be the former. Next time you’re at the range, note how far your average shots travel, not just the pured ones, and that’s your stock number. I guarantee you’ll start hitting more greens.

Stop blaming your caddie. If I give you a bad read, I’ll let you know it. Same if I misjudge the wind. If you want to get mad at me when that happens, I don’t blame you. But often, when a shot doesn’t go the way the player envisions, there’s a glare or mumble in my direction, and suddenly the player who was chummy seconds before is now a sourpuss. More infuriating is when a player hits a good shot and acts like my buddy again, as if what happened before didn’t happen. That’s no way to treat people, especially on a golf course. The worst thing I’ve heard? “You shouldn’t be a caddie if you can’t make that read.” Took a hell of a lot of willpower not to toss his clubs into the fescue.

You’re bringing too many damn balls. I don’t care how bad you are. You don’t need more than six. If you feel secure with three sleeves, that’s fine. But if I see another golfer stuff three dozen balls—and in case you’re wondering, the record is five dozen—into the side carriage, I’m going to lose it.