Golf caddies at America’s most exclusive clubs are privy to conversations that you or I could never imagine. Our nations’s finest golf clubs are home to America’s empire makers, the ‘Too Big To Fail’ CEOs with generation’s worth of fortunes so vast that no man can accumulate that much wealth in one generation. The caddies get to listen in on business meetings that are too secret for the board room (like when one person cannot be seen in the office), the caddies also get to see things like drug use and overhear talk of infidelity.
On the golf course your caddy is there to advise you on the best club for every shot, where to aim, and what (if anything) you are doing wrong, as well as carry your clubs for you. Other than that the caddy is expected to keep his mouth shut and not participate in casual conversation, they are supposed to act like flies on the wall until you need them. These caddies got together in an AskReddit thread to discuss the most WTF things they’d ever seen/heard on the golf course, and while I expected ‘So and so murdered a hooker and buried the body’ it’s a pretty damn good collection of stories, most of which involve lots and lots of blow…So let’s get reading:
Been a caddy for 11 years at a very high end resort. Been a great job. I’ve heard a lot of stock tips, seen a lot of drug use (pills, cocaine, mushrooms ect.) and seen a lot of celebrities and have witnessed 5 hole in ones.
I caddy for my girlfriends dad for extra cash here and there. Mostly for his doctor friends and a lot of them are fucking their nurses and hygienists. Oh and he’s fucking Tim’s wife, but Tim doesn’t tip so…
I wasn’t a caddy (they didn’t seem to have any female caddies at that club) but I did drive the drink cart. I just got hit on by a lot of gross older dudes and bros (usually college boys whose parents belonged to the club) who thought they were hot shit. I made pretty good money in tips.
I saw a guy beat a goose to death. And I heard guys brag about sex and drug use although I never actually saw any.
There was a foursome of women who would play the front 9 twice a week and be totally shitfaced by the end. They shouldn’t have even been driving the carts. I think they meant to play 18 but were always too drunk to continue.
I used to be a caddie. I overheard a group of wealthy business owners asking about strippers and cocaine and where they could find some. The club I worked at had something considered cottages where wealthy guys would stay for the weekend and get drunk and play golf. Needless to say we found what they were looking for and charged a premium.
I was “Golf Services” for a few summers. Basically it meant cart maintenance and caddying services at a 5 star resort in my hometown.
Things that I saw:
— Sinbad (the comedian) trying to convince a guy to quit smoking pot.
Two gay guys “golfed” together twice a week. Both were married and their families frequently came to the club with them the rest of the week. They never actually left the VIP Private sauna, and loud sounds of gay sex frequently were heard from right outside the door. One was a local church Pastor and the other ran a drywall company.
— An old woman who golfed twice a week died on the course once. Just fell over and had a heart attack somewhere on the 10th or 11th tee box. She was found by our cart girl, who happened to be her granddaughter. She tried CPR and failed.
— Overheard two guys talking about solar energy (this was 1996-7) and they were both concerned about the amount of light it absorb from the atmosphere. Direct quote: “Too many Solar panels and it’ll be dark year round anywhere north of the Mason-Dixon line.”
— Saw a super passive aggressive couple who would come in each week, hire two caddies, and proceed to badmouth their spouse to the caddy the entire time. “Oh, nice hook, John. Looks like all that practice paid off.” “Go ahead and tap the ball further onto the fairway with your foot, Sarah. I mean, cheating is what you’re good at, right?” I think they got off on it, because we’d always see them making out in the bar afterwards.
— An Asian dad trying very hard to teach his 7 year old daughter how to golf, every day from 7:30am they would show up and golf the same 9 holes. She seemed to hate it. He was very strict.
I was a caddy during high school. Only job I’ve ever walked out on during a shift. Old dudes hitting on teen age girls. Drunk old guys talking about cheating on their wives. One guy beat a snake to death with his putter.
I was a caddie/bagboy in highschool for a CT Country Club. It was a ton of fun, but I never really got to hear any juicy business gossip.
Best/oddest thing that happened while I was working was seeing people care more about their own golf tournament vs major sporting events. What I mean is I once got tipped box seats at a yankee game only because the date conflicted with the annual club tournament.
There were other things that happened that were awesome, but nothing business gossip-y
A friend of mine drives a golf cart for a few rich people and he made 20 grand two years ago by listening to the stock advice one guy gave to the guest he brought.
and last but not least…
Caddy for 6 years now and still going (part-time now, show up when I want to, or they really need me kind of deal)
I’ll list off some of the best things I’ve witnessed and heard.
Hearing 2 lawyers talk about each others clients and having one tell the other how his client admitted to killing the person but he’s got a solid defense to get him off of it.
Heard multiple members both men and women talk about their adventures of infidelity in their marriages.
Seen members when very intoxicated just whip it out and pee in the middle of a round on tree or such, while having a teenaged girl for a caddy with them in seeing distance.
One guy who worked for the FDA was talking about a massive investigation before it was public knowledge of a certain restaurant starting soon because of E-Coli.
During one of the clubs bigger yearly tournaments, 2 members decided to play bumper cars with the golf carts after that days round was over and one guy (who was in second overall for the 3 day tournament) was ejected and screwed up his hip and it cost him the game.
Well bros, as always I invite any of you bros who are or ever were a caddy to fill out our anonymous ‘TIP OFF‘ form and send us your stories, or if you’d prefer you can just hit me up down below in the comments! And if you want to read more of these comments/stories from the AskReddit thread you can follow any of those links above to head on over.