The first thing I learned when I caddied as a teenager is that no matter what you never have any change. If you’ve just finished hauling some tanned banker’s bag and he asks if you can break a $100 bill—so he can give you $60 or whatever—always tell him you don’t have any cash. He won’t be thrilled about it, but he’ll almost always give you the hundo.

In time, older caddies taught me other tricks, like keeping extra balls in my pocket. If the golfer was playing Titleist 3s, I’d have those fuckers ready to go, and if he shanked his shot into the woods, I’d pretend to search for it for about a minute before dropping a backup ball casually out of my pants and claiming I had discovered the real one. It was a lie that kept us both happy: I appeared to be closely paying attention to his game; he didn’t have to knowingly cheat.

These were some great life lessons, but perhaps the best thing about caddying was that I got to see the One Percent in their natural element. I’ve spied on presumably trust-funded bros as they dumped woodchips into the water cooler at the turn, just for fun. One particularly dreary evening, a mean and hostile gentleman left part of his bag unzipped, and as he walked up a hill, money started falling out. I gathered it all up without question.

I recently asked some current and former caddies what they’ve witnessed the upper class do on the course. Most of the resulting stories were pretty horrible, because as a caddie, those are the ones you remember. As one interviewee noted, “It’s always hilarious to see rich, old white men threaten to kill one another.”

Without further ado:

Peter

I rolled into the country club one morning at my normal start time, 6 AM, to find a black Suburban parked outside of the building we used as a hotel for members and members’ guests. The car was running, and there was driver in it. I couldn’t figure out why this vehicle was waiting outside, and I felt I should ask if he needed anything. When I approached the guy to figure out what was up, he didn’t roll down his window to say anything. He looked at me, turned away, looked at me again, and went back to staring at his cellphone.

Turns out, he was a pimp. One of the wealthy members, on a weekend getaway with some buddies, was renting out the hotel. This member—let’s call him “Mr. Smith”—decided, after getting sufficiently plastered, that it was time for a little extra fun in the carnal sense.

The only issue, though, was that I was caddying for the township’s chief of police that morning. I mentioned how I thought it was strange the driver in the Suburban wouldn’t roll down his windows. When the chief went over there to ask him about his business, the driver responded that his girls were inside, and he was waiting for them to finish up with a client. Without me knowing, the chief then arranged, later that morning, for the police to arrest Mr. Smith and the prostitutes on their way out of the hotel.

By 8 AM, word had gotten out about Mr. Smith’s activities. Not long after, a call came over the walkie-talkies that Mrs. Smith had just arrived to hit some golf balls and play a quick round, despite the fact she knew her husband was on a guys’ weekend.

The employees thought it best to inform Mr. Smith of his wife’s arrival and that it was probably in his best interest to get the fuck out of there. A valet pulled up his car to the back of the hotel, so nobody would notice him leaving. He made it to the gate, along with the pimp and the two prostitutes, where he was detained by the cops.

Later on, housekeeping filled in some of the details. Mr. Smith, apparently, was very into “ass stuff,” they said,” and it got the room pretty messy. However, he picked up the tab, and it was soon cleaned, repainted, and redecorated.

Mr. Smith is no longer a member of the club, as he was kicked out for “indecency.”

Kevin

Growing up, I caddied and worked in the bag room at a prestigious private golf club in central New Jersey. Here are three things every caddie knows: The best golfers are the least asshole-ish guys; if someone’s filthy rich and has no need to show off wealth, he or she is always nicer than the people who are moderately wealthy and have to brag about it; finally, most people cheat.

Every year, the club hosts a golf outing and hires strippers to go around with the players. On each tee, a girl in a short skirt would bend completely over and tee up the ball for the golfers. On one occasion, another caddie and I saw a guy finger one of the strippers while his friends were putting.

After another tournament, during the banquet dinner, a guy had sex on the first tee box. At a different party, a member and his wife were complaining about the meal, and the chef came out of the kitchen, punched the man in the face, and quit. The owner of the club also pissed in the icebox next to the bar that night.

Mathias

I’m a caddie who frequently works on the Latin American PGA Tour. Once, in the Dominican Republic, I caddied for this guy from the South. He loved God and his family, because he told me, repeatedly, that he loved God and his family. He talked about how much he wanted people to come to Bible study. While he played, he recited verses from the Bible. He struck me as a stand-up guy, and it didn’t bother me that he was so vocal about his religion.

On the 17th hole, though, he smashed a driver farther than I’ve ever seen, and I’ve seen a lot of drives. I said “nice shot,” or something to that effect. He responded with, “We have a saying down in the South: I wouldn’t even hit a nigger that hard in the face.” It was, to this day, the most racist thing I’ve ever heard.

Michael

I recall an interaction on a wide-open par five fairway between the a randy member of a foursome and a concessions cart driver. This was at a private course in New Jersey, where the clubhouse was an old fox hunting manor and Wall Street executives would helicopter in for an afternoon of golf.

The driver was a young girl, about 20, and cute in a sexy way. She wore white Chuck Taylors and short shorts. The randy man, who was handsome and probably like 45, ordered four beers with a smooth, bedroom voice. She smiled and went to the cooler, where she bent over to reach the bottles of beer. She handed the beers to the men, and the smooth guy paid her. She then said, “Thank you, sir.” I assume the tip was large.

The guy wasn’t finished, though. He dropped a ball onto the fairway: “Listen, sweetheart, if I hit it on the green, you’re coming to dinner with me.” He had a thick Italian-Jersey accent. I could see her round cheeks. He took a practice swing. He took another. He stepped up to the ball, cleared his throat, and maneuvered his body into pose for the shot. He drew the club back and came hard down on the ball, striking it at the toe of the club, launching it straight at the concessions driver, rather than toward the green. The girl had been standing in front of the cart but wasn’t hit. The men rushed toward her, making sure she was OK, panicking at how close she could’ve been knocked out. The randy man’s smooth voice went up a few octaves.

Sammy

The summer before freshman year of high school, I caddied at this course in an extremely wealthy part of Denver. I don’t have much experience with other country clubs, but I can’t imagine you could get any more cliché than this Stepford-esque fuckhole. The clubhouse looked like the hunting lodge that the woman-hater in the OG Disney Snow White hung out. I’m 13 or 14 or whatever, questioning my sexuality, super into punk rock and rap and anything that would piss off my suburban parents and peers. My best friend was into the same, and his mom forced us into this caddie program.

The next morning, my friend and I showed up on the practice green in ripped black jeans, surrounded by khaki-wearing assholes. The caddie master’s name was Skip and he was all kinds of racist and anti-Semitic. The dude never looked me in the eye once, and he was always doing terrible shit, like uncomfortably hugging the only two girls who worked there for horrendously long periods of time. Yeah, I fucking hated Skip.

There was a lot of despicable shit, but the worst of it really was the fact that I didn’t get paid. Skip operated on the “chit” system. After you worked your round for the day (if you were lucky enough to get a round), you handed your chit to golfer whose bag you carried. He would rate you and write down the amount he wanted to pay and tip, and then you would cash out in the caddie shack with Skip.

Not a completely terrible idea, except I never got paid. Skip would say the safe was broken, or locked—stupid excuses. I can’t claim it was discrimination, but whatever the fuck was going on, it didn’t happen to anybody else. After a while, my mom (who should never be fucked with) realized something was wrong. I told her what was happening—that I wasn’t getting paid—and she stormed in there, got all the money I was owed, and I never fucking went back.

A few years later, my mom was telling a coworker about the whole Skip situation, and it turned out this lady was the wife of one of the loaded higher-ups at the club. He said something, and they fired Skip. So I guess not all rich people are terrible. Just an overwhelming majority are.

*Last names have been omitted, and some names have been changed, at the request of the subjects, for privacy.

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