Good caddies are patient.
This might spar with the qualities you’ve come to expect from loopers: nomadic, cash-crazed, jittery. Those characteristics are pretty standard. But like any animal in the wild, feverishly searching for their next meal, a good caddie will recognize when it’s better to play the waiting game than spend valuable time and energy chasing a dead end.
There’s no such thing as a sure thing in the shack. If you’re hoofing bags at a resort like Bandon Dunes, Pinehurst, or courses that golfers will hop on planes to reach, tee times and subsequently caddie-player pairings are relatively predictable—caddies will have some advance notice on their schedules for the upcoming weeks.
At everyday clubs however, where walk-up, spur-of-the-moment play fills in a sizable chunk of the daily tee sheet, it’s borderline impossible for caddies to predict what their next day on the job will amount to. And in a profession where hierarchy, tenure, and accountability dictate who makes money and who walks away with air in their pockets, riding the bench to show you can stick it out is a surefire long-term strategy.
Let’s break this down: say 50 caddies roll up to the shack at 6:45 a.m. on a Thursday morning, sniffing the ground for loops. They bum-rush the caddie master, frothing at the mouth, scouring for the day’s tee sheet. Only seven foursomes teeing off between 7:30-10:00. Shit. That means at maximum only 14 caddies are getting out in the morning. In most cases, those 14 loops are going straight to the seasoned vets—the bag bandits who grind it out every day, who know every yardage on the golf course from memory, and who can tell you where every putt is breaking without even looking at it.
The remaining caddies have a calculation to make: how long am I willing to wait for a potential walk-up loop in the afternoon? Inevitably, a chunk of caddies who rose at the crack will mutter a “fuck this” and head back home to sleep. Others will stick it out. The potential payout—upwards of $200 for the day—is just too tantalizing. This ecosystem demands optimism, breeds patience, and necessitates some bench-riding.
This hours-long waiting room period turns the caddie shack into an equal parts gambling arena, mental hospital, trap house, philosopher’s den, and beat laboratory.
You learn to tolerate—almost enjoy—these long stretches of downtime, despite knowing all-too-well that you’re not making a dime. Everyone has something to say in the caddie yard, and with nothing but time and a pack of smokes on-hand, you’ll look for any form of entertainment possible: outlandish conspiracy theories, freestyle rap battles, sex stories, sob stories, sobriety stories, drug stories. If you’re lucky, your caddie shack will have some amenities to spur the heavy-onset boredom of waiting for a loop to turn up. We had a ping pong table, a couple rank couches, a glitchy ten-channel TV, and a basketball hoop.
During rain delays or slow days at the course, the shack’s back room would be packed tight—young caddies swinging from the light fixtures, the humid New England summer air beading on the cloudy windows and recycling into musty vapor once more. Thirty caddies huddled around the ping pong table, putting single dollars, loose joints, and future loop earnings on the match in front of them. Wimbledon-inspired silence settled before each serve, erupting in pandemonium with every point.
A fourteen-year-old caddie attempts to pass through the gauntlet and reach the bathroom in the corner, only to get shoved out of the way and smashed with a paddle. “Interference! Redo that point!” yells one spectator. “Fuck that, there’s no way he was returning that anyway,” rebuts another from the back, who clearly had a couple bucks or half a sandwich riding on the action. The best case scenario would result in the caddie master bursting into the back room to interrupt the game with some fresh loop assignments. But that was a rarity.
Once the round robin tournament wrapped up, the hoard would meander back out to the fresh air—several breaking away to go get high, one or two hanging back to work on their rhymes, others deciding they’d hung around long enough for the day. Fine by me, piss off—less competition. Some caddie would be in the corner freaking out because his new headphones were just stolen. And despite knowing exactly who the culprit was, nobody’s going to help the kid out because, well, a good caddie ain’t a snitch either.
Some caddies would take the opportunity to run errands in delay periods. One day, when I was 16 and still fairly new to the hustle, we got hit by a chunky thunder and lightning cell on the course. Everyone was shepherded off, and we had a minimum wait time of an hour before we'd be allowed back. We had some time to kill, and an older caddie in the yard asked me for a lift to a nearby store to grab something to tide him over. Eager to please, I agreed, and we skirted over to a small strip mall. I waited in the car. A few minutes passed, and the guy hops into my backseat with a six-pack of Dos Equis. "Alright, let's get outta here," he said, as he popped top on his first of what would be all six beers. It was 10:15 a.m.
Some of these long waiting days paid off with a late-afternoon job. Most amounted to nothing more than hanging around and swapping white lies and hot takes with fellow loopers. But despite driving home with just as little money as you started out with that day, chances are you learned something about somebody. Maybe you got a little better at telling your own story. Regardless, you’re ready to lace up the boots and do it all over again tomorrow.