It’s the best of jobs and the worst of jobs, depending on whether one is at the age of wisdom or foolishness. If one is only 19, with two whole years of college left and plenty of time to figure out the next step, there are few places better than the caddyshack to waste away a summer. But if one is already 19, with a declared major and a career in mind, the caddyshack is the most constricting straitjacket, with straps of untaxed $100 bills and locks whose only key lies in an internship offer.
This was the sixth summer I’ve wasted in a caddyshack and I was somewhere between yanking on my locks and drooling from the drip of the doctor’s IV that has drawn me back, summer after summer, to carry two 20-lb bags in the hot sun for four hours. I’ve been humiliated, demoralized, verbally abused, and I’ve been given business cards, beers, and insight into the psyche of 50-something-year-old children.
My experience with the asset-slinging and stock bell-ringing began in the spring of eighth grade, when my parents realized summer was approaching and I was at an awkward age–too old for summer camp, too brashy for Teen Travel, and too young to entertain myself every day. But there are few jobs for teenagers, and even fewer for those too young to obtain working papers.
Neither of my parents golf, and the starter club set Santa had brought me the previous year was still collecting dust in the corner of my room. But for some reason, they figured caddying might be a good job for a 14-year-old with too much energy (I had been cut from all travel sports teams at this point and had yet to begin my remarkably underwhelming high school football career).
I looked up “Golf Clubs” in the yellow pages, called the first club alphabetically, and received an invitation to come train once a week before starting in June. In the spring training sessions, I caddied for the caddymaster, who told me where to put the bag down, how far to place the bag from the golfer, and when to pick the bag up. That isn’t to say caddying is easy, but it’s not hard to imagine an Air Bud caddy—and he might even be better than most humans because he wouldn’t understand the golfers’ backhanded remarks.
But caddying is much more than dog work, and requires a forbearance I never anticipated needing when I first started. Caddying is not following the golfer for 18 holes, but leading him, hoping that with the right information about the wind, the distance from the hole, and the uphill trajectory, this middle-aged, decrepit, lonely, crusty millionaire might relive the athleticism of his high school days, before he shipped out for World War I.
Indeed, it takes a couple to caddy, both a golfer open to criticism from an adolescent, and a caddy willing to take the most vitriolic verbal degradation, in a mutual hope that the golfer might finally feel better about his self-esteem, and the caddy might have enough money for beer for the entire school year.
I did not come to this realization the first few summers I caddied. I quickly assumed I was to speak only when spoken to, and this allowed me to almost entirely remove myself from the game emotionally. I was a robot carrying a bag, announcing a distance to the hole, and moving on to the next shot.
I had been wired and programmed to behave this way by the other caddies in the caddyshack. The average caddies at my first job were 37, and had worked at the club since they were 16. Wide-eyed and curious, I was fascinated when they’d chain-smoke Newports, scratch-off lottery tickets, and itch at their track marks. Mother would not approve of this.
I quickly picked up on their work habits, although I had no reason to have any such habits. I slugged up hills carrying the bag, not because I was hungover but because I was lazy. I didn’t talk to members, not because I was slurring my words, but because I was scared to use them. I sulked when there were no loops, not because I needed to score before withdrawals kicked in, but because I had been spoiled into expecting a perpetual flow of untaxed income.
Caddying was nothing more than work, and grunt work at that. I learned to resent the early-morning wake-ups because I watched cab drivers, deadheads, barbacks, stoners, and dropouts—all caddies—resent the early morning wake ups.
That changed in summer 2016, after I graduated high school, and my parents decided I was old enough to spend the summer at my grandparents’ house on the East End of Long Island, in one of the last hidden neighborhoods of the Hamptons, called Noyac.
In Noyac, hedges are looked down upon, and convertibles are parked in front of cottages that could double as garages. During the day for kids, it’s a bike track more intricate and storied than the Tour de France; at night, it’s a playground lit by fireflies and scored by hide-and-seek counts. Crickets are interrupted by the cracks of teens’ first beers, and the moon is never taken for granted. It’s a community of bungalows—the antithesis of the shallow flash of East Hampton, which has three separate Ralph Lauren stores on Main Street.
In Noyac, there was once a club as casual as the neighborhood. In the 1990s, new members at Noyac Golf Club payed $8,000 to join. But spots at nicer clubs in the Hamptons dried up as more rich people made partner at Goldman each year. The newest members, who paid six figures to join, are in the process of manicuring Noyac to the standards of the authentic WASP country club, into which they so desperately wish they could get admitted.
One of the marks of a real country club is the caddy program. If a club has real rich people, the kind who employ millions of workers in sweatshops throughout Asia, it will employ professional caddies—grown men who carry bags for members half their age. At such clubs, people work in hospitality for careers. But Noyac’s clientele isn’t elite enough to attract such a workforce. Instead they hire kids like me.
In the shady corner of the service lot, the caddyshack at Noyac Golf Club is a wood deck with high picket fences on three sides, and a tarp roof to block the sun. In the middle is a glass patio table rescued from the side of the road. Around the table are four comfortable patio chairs, and three white, wooden folding chairs, and in them sit a band of adolescents as loyal as The Sandlot, as sophomoric as Jeff Spicoli, and as enterprising as Ferris Bueller.
The caddies at Noyac were not junkies, but juveniles—normal kids from down the block who played golf for the local high school, went sledding down the ninth hole in January, and snuck Cuban cigars out of the snackbar, which they knew was unlocked weekdays after Labor Day.
But with this coming-of-age innocence existed a level of shrewdness not typically found among teenagers who work retail for the summer. Untaxed cash raged like fire in our khaki short pockets. More money circulated across the caddyshack table than the average Vegas blackjack table, and four hours of hard work could disappear with the roll of the dice.
The love for gambling often coexisted alongside a love for golf. We were allowed to play the course Monday through Thursday after 3 p.m., and with this freedom came a newfound appreciation for the game. I had playing privileges at the first club I worked at, but never coworkers who were sober enough on their days off to golf.
At Noyac, I didn’t develop a love for playing golf, but by playing every once in a while with caddies who knew how to golf, I realized, and grew amused by, how difficult the game is, and how much it tormented my clients.
After three years of walking in silence, I was now working with guys who could advocate for a low 5-iron instead of swinging for the fences with a 3-wood. I didn’t need to know the difference between the shots so I wouldn’t get fired, but I wanted to know so I could laugh at the member with the other caddies in the shack. The most common caddyshack talk often revolves around the immense stupidity exemplified on the course by some of the world’s most savvy businessmen.
Over the course of my days caddying, I’ve found the best way to decompress after a sweaty Summer Sunday afternoon slinging bags and selecting clubs is to sit in an air-conditioned room and turn on a PGA tournament. The best remedy for watching so much bad golf is to watch a little good golf. I could never do anything close to what Phil Mickelson does on TV. But I can kind of tell a member how to do it.
Featured Graphic by Anna Tierney