Don't Bogie That Beer! Secrets of a Hamptons Caddyshack

“It’s kind of a different way of life, because you can really just live your life one loop at a time,” said Gunner of his life caddying at a very exclusive private Hamptons golf club which is often bathed in a nice ocean breeze. He’s 25; back home in Glasgow, he’s studying to be a dentist. “You always know you’re going back out the next day. So it’s quite a surreal environment. ”

“It’s just something you do between sessions,” said Coco, Gunner’s 22-year-old friend from Glasgow. By “between sessions” he means between bouts of drinking.

While the work itself—digging around for balls in the fescue, lugging two sets of golf bags, praying for the moment when you put that flag in the 18th hole—might at times feel like grunt work, the way of life in the shack—two long pine planks that run along either side of a covered tent, tucked away behind a well-groomed hedge—is rarely dull.

“It’s really cool because it’s quite multicultural,” said Coco. “There’s Irish, Scottish, Argentine, American and Antiguan guys. We’re all hanging around together.”

“It’s quite a tightknit group,” said Gunner, sipping on a Heineken on a recent night at a local dive bar called Wolfy’s.

There are about 37 caddies altogether working at this particular club. And some days for hours on end, when there’s no play for whatever reason, they will all be lined up on the pine planks, waiting.

“It’s very funny; you have the Antiguans, who are always like the loudest in the morning,” said Coco. “Always shouting at each other, but that’s their culture, you know, arguing. They’re always trying to sell you stuff—sell you their golf clubs or buy your golf clubs.

“I bought a 5-wood,” he admitted. “You haggle all day and they’ll be like, ‘One fifty.’ And you’ll be like, ‘No way. Sixty.’ And they’ll be like, ‘Coco, I don’t like that price but let me get back to you in a few hours and I’ll see what I can do.’”

“One of the guys tried to buy Beano’s sunglasses,” said Dee, 22, of her older brother; they’re from just outside Dublin. “He’s like, ‘They’re not for sale.’ The guy’s like, ‘I’ll give you a really good price.’”

Dee is a cute, sun-kissed blonde. She has a year left of university, where she is studying exercise counseling. She arrived a week before her brother.

“I came over alone—didn’t know anybody at all,” she said proudly. “And I walked into the shack, met Coco. Everyone was just kind of looking at me going, ‘What is she doing here? There’s no way she’s going to be able to carry bags.’ The guys had bets on if I would be able to last 18 holes.”

“She’s turned into quite a dirty-minded girl up over at the shack,” Coco said.

“Well, if you sit in the shack with 40 guys or so every day, they start treatin’ you like one of the guys,” said Dee. “You have to go with it.” She’s adamant, however, about the guys saying please and thank you when they ask her to move down the bench.

The conversations Dee would prefer not to hear generally revolve around the events of the previous night. Most evenings, they roll out in force, a posse 25 caddies deep. Kobe Club, Rowdy Hall, Tavern, Talkhouse, Syros and Sloppy Sunday’s, and The Point in Montauk. The night before, Coco had dropped $200 on bourbon and beer. He’s the reigning lady-killer, having smooched 10 and made sweet caddy love to two.

He and several other guys are living in the basement of a nice house; Gunner lives in a tent on the lawn. In less than a month, Gunner has already lured a “completely hot blond girl” into the tent. “I fell asleep,” he said, shaking his head.

“One of our friends—just say he was an Irish caddy—he went out one night in Montauk,” Coco said. “And he couldn’t remember the end of the night. And he woke up on a yacht with his pants off, next to a sleeping 60-year-old woman.”

“That got a lot of laughs in the shack,” said Dee with disapproval.

The Antiguan guys are always admonishing the Scots for drinking too much rum. Meanwhile, the Argentine boys are always groomed to the nines, making everyone look bad.

A few weeks back, they were all having a jolly time at The Point in Montauk. There was this American kid who started giving one of the Argentine caddies a hard time. “The kid threw a cigarette in his face,” Coco said. “So we went over and said, ‘Well, man, I think you better go home now. There are about 40 of us.’ And he was like, ‘O.K.’”

Don't Bogie That Beer! Secrets of a Hamptons Caddyshack