Secret Life of a Country Club Caddy

From faking holes-in-one for the promise of tips, to indulging the every whim of spoiled suburbanites, one of the golf world’s silent assistants tells all.

Secret Life of a Country Club Caddy

My testicles were unharmed by the force of the descending golf ball. In my final summer as a country club caddy, I stood next to an elevated green while the golfers teed off 150 yards away and forty feet below. One of the players popped his ball up so high I lost sight of it in the hazy sky, forcing me to pretend to follow its path towards the green. All caddies do this. On several holes, such as this one, we were expected to leave the golfers on the green and go ahead to get a better view of the next tee shot. Sometimes we don’t see that shot and have to improvise.

I craned my neck from left to right, pretending to follow the ball as it rose and fell and…smacked me in the nuts. Fortunately — and I can’t stress that word enough — I had taken a wide stance and had my hands in my pockets, creating a trampoline effect in the crotch of my khaki shorts. Instead of suffering the pain you’d expect from taking a golf ball to the groin, I was able to act like nothing had happened.

“Did that get you?” the golfer asked when he arrived at the green.

“Nope, no, just took a weird hop off a tree root.”

I don’t think he believed me.

I caddied at a country club in Westchester County, New York, during my high school and college summers, starting in 2000. My brother had caddied there and said it was good money. Caddying seemed better than the camp counselor jobs many of my friends had. There was no interview and I didn’t have to submit a résumé or even provide ID. I just showed up one day and sat on the bench.

I did a lot of that my first summer. The caddy shack did not have a TV or board games or ping pong tables, and smartphones weren’t mainstream until my last year or so. Waiting for my name to be called one morning, I tried to count the dimples on a golf ball, a nearly impossible task without a marker. There were newspapers caddies had brought in from the city; always the Post or Daily News, rarely the Times or Journal. Given the downtime, it was surprising how few books I saw around the caddy shack. Maybe it’s because we’d have nowhere to put them. The waiting list for the dozen or so mini-lockers was long; if half the caddies had suddenly died I might have gotten one.

The caddies spanned all ages, races and backgrounds, though there were no women. We divided into groups for conversation: The eighteen-to-twenty-five year-olds talked about girls and partying; the thirty-to-forty crowd preferred sports and television shows; the senior group complained about their health problems. Some of the nicest guys I’ve ever met were caddies; others were crude, standoffish or nasty. I once saw a caddy rip a newspaper to shreds just so nobody else could read it.

After days of sitting, the caddy master — has there ever been a more appropriate title for a boss? — felt I’d paid my dues and sent me out for my first loop. There were three golfers and I was paired with a veteran caddy, Tim. As a “super looper,” he’d carry two bags; I’d only get one since I was a rookie, also known as a “rabbit.” Tim was the only caddy I saw use sunscreen. “Puttin’ on the war paint,” he’d say as he applied it to his face.

On the third hole, Tim pointed at me from across the fairway. I thought it was an enthusiastic acknowledgement (Hey, you’ve got this!) so I pointed back. He emphatically motioned again and tapped one of the bags he was carrying. I turned my head and realized his intention — my bag was at such an angle that all the clubs were about to spill out. I fixed it, but things didn’t get much better from there, as I was unsure which flags I should pull and when to go ahead to the next hole. I also lost a ball, the cardinal sin of caddying. And yet I wasn’t fired or even yelled at. Walking off the eighteenth green, my golfer handed me two $20 bills. I cleaned his clubs, put them in the bag room and returned the next morning.

Country club caddying is much different than working for a professional golfer. You are not asked for distances on every shot or to read the green on every putt, nor do you have to be as concerned with the emotional state of your golfer. It has just one requirement: an ability to walk five miles with up to fifty pounds on your shoulders. Patience certainly helps. Even as a veteran, there were times I’d wait for a loop from seven a.m. until noon. There was an internal struggle between wanting to get on the course and knowing that’s just the start of your work. “Gotta make a day’s pay,” Billy, who was also a full-time firefighter, would always say when you asked if he was sticking around.

Leaving was not easy, anyway. Communicating with the caddy master was like deciphering code. I’d ask whether it was worth staying and get a shrug in return. He’d catch me trying to leave and say, “Hey, where do you think you’re going?” and I’d slink back to the bench like a dog who knows he’s misbehaved. Two hours later he’d see me sitting there and say, “You’re still here?” My friend and I were terrified of him and would play rock-paper-scissors to decide who’d talk to him. But he was fair. If he made you wait around one day he’d get you out early the next, often with a high-paying group.

Once on the course, I learned to zone out while still paying attention so I could get from the first tee to the eighteenth green in what seemed like less time than it really was. Splitting the round into smaller benchmarks was key. I’d tell myself, Just get to the fourth tee, then get through seven. I’d get a free Gatorade at the turn (after nine holes) and a hot dog for a dollar if I wanted. After I climbed the big hill on thirteen, I felt like I was heading home.

Sometimes I’d lose both my focus and sight of the ball. It was never good when I turned my head as if the ball was passing, only to hear it land twenty yards behind me. But even worse was when I didn’t hear or see it at all. This warranted one of several stall tactics. The key was to let the golfer lead me to his ball, presuming he saw it. I’ve untied and retied my shoes, gone to the nearest water fountain to wet my towel, cleaned every club in the bag, stretched — anything to kill the time until the golfer walked towards his ball. Of course, if neither of us saw it, I was screwed.

When the round was done, I’d put the money from each golfer in separate pockets. Once they were out of sight I counted it. A veteran looper told me the rate was $37.50 a bag when he started in 1996. It was $40 to $50 when I started and $60 to $70 by the time I stopped in 2008. Now it’s up to $80 a bag, minimum. The super loopers doing two a day are making at least $320 in cash.

After a summer of single-bag loops and occasional one-and-ones (one bag and one putter from a cart-riding golfer, for half the fee of a bag), I graduated to doubles. The difference between carrying two bags compared to one is less than you think, physically, and if you’re going to spend two hours sitting and another four on the course, you’d rather get $100 than $50.

Although, working for two golfers meant twice as many complaints. There are a few I’ve heard more than a hundred times: “I barely touched it” — said when a golfer hammers a putt ten feet past the hole. “That’s not fair. I hit that sooo well” — said after a shot lands in a sand trap or the rough or some other undesirable location. And my favorite: “The ball’s just not travelling well today” — said when a golfer’s shots repeatedly come up short of the green. I’ve never heard a golfer say the conditions were making the ball travel farther than usual. One time a woman I was caddying for hit a tree — in plain sight no more than thirty yards away — and yelled at her husband, “Why didn’t you tell me that tree was there?”

It was always amusing when a horrible player would ask how far away a hole is and I’d tell him “about 135, 140,” and he’d say, “Well, which is it? 135 or 140?” as if it mattered. More often than not he was going to shank it sixty yards anyway. And when he did, he’d likely blame it on his clubs. As I heard one golfer tell his annoying partner, “It’s not the arrows. It’s the Indian.”

I saw caddies cheat for their golfers by moving a ball from the rough to the fairway. I even heard about a “hole-in-one caddy,” fired a few years before I started, who turned good shots into lifetime memories on holes where the golfer couldn’t see the green’s surface, in the hopes of getting better tips. It sure as hell wasn’t worth losing my job over something like that and I didn’t care enough about how well my golfer played.

That was true of most caddies. For every Doug, who could give you a shot-by-shot recap of entire rounds, there was a Jimmy, who once said, “I don’t remember who I caddied for yesterday and that’s because I don’t give a flying fuck. I remember how much I got paid though.”

Pay was the most important factor in determining a loop’s quality, but a really hot day was no fun, especially during the summer, when they made us wear thick green bibs that served no ostensible purpose. The heaviness of the bag matters, though perhaps more so for the 150-pound high school kid I was than for most. When I first started, a bag stand was a luxury; now it comes standard. You couldn’t trust a bag to remain upright on its own, a lesson I learned when a bag I had left standing near the green came crashing down just as my golfer was attempting what should have been an easy putt. He missed, and shot me a stare that implied it was my fault.

Club covers were annoying; we expected them on woods, since they prevent nicks and loud clanking, but they started to appear on putters in my later years. I stressed over whether to hand the putter to my golfer with the cover on or off or if I should stuff it in his bag for the entire round. With both hands usually full, covers were just another thing to deal with and possibly leave behind. My feelings about the golfer with covers on his entire set of clubs are unprintable.

But a good payday makes caddies overlook most things.

We all got paid nicely when a company brought employees to play the course. These outings occurred a few times a month and caddies would often get the standard rate from the caddy master, plus tips from the golfers. They often took carts, so all we had to do was carry the putters and point the players in the right direction.

Outings always began the same way, with the caddy master arranging for more caddies than he needed to show up. He held his clipboard and read off our names: “Diego, hole six. Barnes, seventeen.” We felt like prospects at the NFL Draft. Once he sent the unfortunate extras home, he’d give us a speech about not drinking on the course — there was usually alcohol stocked in the coolers for these events. “Can he fire us all?” a rebellious caddy once joked. The caddy master shot back, “You don’t want to find out.”

There were often Dewar’s or Coors Light models serving drinks during these events. The golfers tried to act smooth around them and show off. One time a particularly bad golfer hit a beautiful shot off the tee where the girls were stationed. A few holes later, again with the ladies looking on, he put one close to the pin.

“If there was a vagina on every hole you’d be a scratch golfer,” one of his buddies said. Another added, “No, he’d be a snatch golfer.” This kind of humor was not uncommon in an arena devoid of females. One afternoon, one of my golfers was peeing behind a tree and my fellow caddy fought back laughter to tell me, “You gotta go the extra mile. Go hold his dick and shake it for him.”

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Drew Weing draws comics and illustrations, lives in Athens, Georgia, and is married to cartoonist Eleanor Davis.