Best stories from working at a golf course

For all my current and former caddies, cart boys, assistant pros and head pros ( shout out @ClubProGuy ) what are some of your best and funniest stories from your tenure driving the range picker?

*Note: names and locations have been changed to protect the innocent.

I once caddied for the man that invented the pager when his normal caddy/manservant called in sick. The guy’s Bentley had “Beep1” on the license plate. Picture in your mind a shorter, Hispanic Colonel Sanders. He was the club’s worst offender for pace of play due to always playing a 6-8 man scramble by himself. He couldn’t hit the ball out of his shadow, but would keep hitting until he was satisfied with a shot. I got to ride in the cart and carried a shag bag to pick up the errant shots. I also had to tee up every tee ball for him. The round lasted nearly six hours and his honest score was easily 110+. After cleaning his clubs and loading them into his Bentley I think he’s going to stiff me. Before he would pay me, he asked me to sign his score card so he could turn it in for his handicap. I signed for a 68. My integrity was worth a $100 tip.


Caddying for a member guest at the place I had been looping at for 6 years prior.

A guest of one of the members pulls into the parking lot in a beautiful Ferrari while my member is warming up on the range. Come to find out that we’re paired up with their group for the first match of the day. The Ferrari guy can’t stop talking about how much he loves wine, how he just went to Napa, and is planning to open a couple of the $500 bottles he bought out there while he and the member he is the guest of with are at dinner tonight.

Well, mind you - it’s the middle of summer in the Chicago suburbs. Had to be in the mid 90’s that day. We finish the round and, prior to heading back out for another 9 in a new matchup, my member wants to hit a couple of shots since we had finished playing an hour or so prior. We walk past Ferrari guy going to his car and he opens the driver door to find wine had exploded everywhere in the interior. From peeking in briefly, it looked like the scene in Pulp Fiction when Travolta accidentally shoots that guy in the car (spoilers).


I got accidentally locked in a storage shed for at least an hour or two


I was a junior caddie when I was a kid. Got paired up with a member that had a powerbilt staff bag. The sucker was so heavy and had a lightning bolt on the shoulder strap. The tip of that bolt jabbed me in the neck for 5 hours. Not worth the $12 and hot dog at the turn

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Was a cart boy for a summer. Assistant pro at the club repped TaylorMade clubs and had the big staff bag with all of the latest clubs. At the time, he was posting scores in the high 80’s and getting frustrated with his game. One day he came back to the shop after playing without his clubs on his cart. My buddy asked where they were and the pro said “I got so mad that I threw them in the pond on 18. If you want to go get them out, you can have them.” My buddy spent a while searching the pond in his good clothes before he figured out the deal.

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falling asleep on the fairway mower and waking up 5 feet onto the green. Luckily no grass was harmed


Worked as a cart kid in high school. There was an elevated par 3 and you had to drive down a winding dirt cartpath with a pretty steep grade to get the green.

On the way down, there is a sharp 90 degree turn. A guy floored it down the hill and tried to drift the cart around that corner. He slid the cart on the dirt and launched it into the pond 25 feet down the bank next to the next tee box. We had to call in a crane to come fish the cart out.

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Weed eating along a creek and see a big water snake with a pretty good catfish in his mouth. Told my buddy that we didn’t need the snakes catching all our good fish. I took a ball I had found out of my pocket and fired my best fastball at the snake hoping to scare it into letting it go. Lo and behold the ball hits it directly in the back of its head and it releases the catfish. The snake just rolls over and disappears. My buddy, amazed at my accuracy, tells me “Cart, you’re headed to the majors with that control.”

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I’ve worked at a few courses in my day, but, in college I spent a little time as a caddie at a resort course that shall remain nameless.

One day(after a morning shift), I plucked a used lefty 7-Iron from the lost and found and went to hit some balls for S&G’s. There just so happens to be a resort guest that is hitting balls next to me. This person is, in no uncertain terms, a dick. He proceeds to ask me what I do, and then tells me that he’s glad he doesn’t have me that afternoon because a good caddie has to be a good player. [Side-note: I’ve broken 80 left-handed (fraternity gamble that paid off), and am a right-handed college golfer, and this cat hasn’t hit a solid shot since Grover Cleveland’s first term.] He then proceeds to tell me that he’s a single and has never played the course; I offer to serve as forecaddie. He says ‘sure, bring your clubs, I’ll teach you a few things.’ I apologize and say that my clubs are at home, and I might have to borrow some clubs from the barn. I grab a rental set of right-handed clubs, and upon arrival at the tee, say ‘ah I’m not that good anyway, and we don’t have any lefty rentals, so I might as well use these.’ The guy says, ‘if you hit the fairway I’ll give you a hundred bucks.’

…a 293 yard buttercut into the heart of the fairway later, I picked up a tee to see his smiling face. ‘You lyin’ sonofab$&ch…gotta hand it to you.’ He pulled a $100 bill from his pocket and invited me to play the rest of the nine holes with him. Ended up caddying for him the rest of the week, and he is now a member of the club.

I have yet to use that hustle again.


Working at the same course, one of our assistants had to have been part of the inspiration for @ClubProGuy. Some of his highlights:

Missed the member-guest because he chose jail time en lieu of paying numerous parking tickets.

Had his car stolen from his apartment. A few months go by where he walks to work and makes us pick him up in a cart outside the gate. Me and a few other cart guys crank call him saying we were the police and his car had been found. His elation was quickly dashed when guys audibly lost their composure.

His fiance signed them up for “round up for savings” at their bank where each debit card transaction is rounded to the whole dollar and placed into savings. This over drafted their account before the week was out.

Giving a lesson to a new member he borrows the member’s brand new Titleist 907 D1 (triangle driver). He immediately hits a reverse shank between his legs and the club snaps.

Spent most of the 1980’s playing in a KISS cover band.


I marshal at a very nice course every Friday morning just to help out the head pro because the course I work at is technically a resort and most weekends are “Stay and Play” players. This resort has attracted a lot of celebs over the last 10-15 years. President George W .Bush, Aaron Rodgers, and Johnny Manziel all have pictures and memorabilia in the pro shop. Pat Summerall hit the first shot ever on the course. Anyways, you get the point. So I am marshaling (aka finding golf balls and watching guys hit shots when a man with long white hair and a big white beard gets of out of the cart to hit his ball. He hits your average golf shot and says something to his buddy and they climb back in without sanding his divot. Remember, the course I work at is nice, I mean really nice. Number 1 on most of the top golf courses in Texas nice. So I drive up to the divot and fill it in and then drive up to the green and just politely get out and remind the gentleman to repair their divots in the fairway. They all nod and the man that looks like Santa Clause walks up and shakes my hand and apologies and it’s Buddy Garrity (Brad Leland is his real name) from Friday Night Lights the TV show. ( He’s also in the movie as well but isn’t as well known for that part) Anyways I am in complete shock because I’m in Texas where football is king and I have just told this man to replace his divot and it turns out he’s the main character in my wife’s favorite TV show. Pretty embarrassing. He was a super nice man and he is exactly the same kind of guy in real life as Buddy Garrity.

Needless to say I have not told anyone to fill in a divot since.


Thank you for coming forward and sharing your story.


This thread is giving me life. Please keep them coming.

I’ve worked at courses since I was 12 and I’ll keep thinking on some good stories. The only one that keeps making me laugh is a really simple one. We had this ranger at our course that was a huge lovable klutz (a la Kevin from “The Office”) and we would constantly set him up for embarrassment in front of large crowds. Our favorite recurring trick was to back his cart (he always insisted on having the fast one) in front of something loud and/or fragile (a trash can, a set of rental clubs, etc). Then we would put the cart in reverse and disable the reverse buzzer. He’d waddle over to his cart and make some quip like a movie character and then slam on the gas. He’d get jerked backwards and whatever was behind him would come crashing down. We probably did it 100 times and he never checked beforehand to see if the cart was in reverse.

Simpler, more sociopathic times.


Bear with me here…I was working at a club in the midwest. The members voted to rebuild the club house so for one season we had to work in a dusty back parking lot using gas carts out of a pro shop that was a double-wide trailer.
We had a small but faithful membership that was 99.995% Jewish and many of the members had close ties for generations. There was one group that received extra special service- they were like the elder statesmen of the bunch. These men were all in their late 70s and 80s and from the old country. One of them was a child survivor of a WWII concentration camp. For the sake of story, we will call him Saul.
Saturday mornings were men’s shotgun 8:30 start. The members would pull in the lot, open trunks and we’d load their bags and they’d go park wherever. It was mess. Picture 40 golf carts and 80 Mercedes S550s all in a dusty lot the size of a basketball court with our double-wide pro shop in the corner.
One fateful Saturday we had all the carts loaded up and the players started driving out to their respective holes when, suddenly and unexpectedly,Saul flips his cart into reverse to go around the cart in front of him. He doesn’t realize that his 85 year-old friend Hershel is walking up behind the cart. I see the whole thing unfold and I am screaming STOP as loud as I can, but Saul can’t hear me and he nails Hershel. Totally floors him and runs half of his torso over before realizing what he’s done. Hershel is in horrible pain, he’ s shocked and part of me thinks he’s dying under a green EZ-GO. I’m freaking out and the rest of the staff is freaking out. Saul, meanwhile, bails the scene. He was probably halfway down the fairway in the foursome-turned-threesome that is group 13A when the ambulance arrived. Marinate on that for a second. Saul ran over his 85 year-old friend he’s played with for 25 years and he just goes right to the tee as if he ran over a branch.
Herschel goes to the hospital and we have to call his family. It’s just terrible. These were tough phone calls to make. About three hours later Saul comes into the double wide as he’s turning to 10 tee. He calmly asks “How’s Hershel?” And I say something like “He’s at the hospital, we’re not sure how serious it is or if he’s even going to make it.” Saul, grabbing a handful of bite-size Snickers from the snack bowl, looks at me , shrugs his shoulders and says “He had a good life.” And then he walks out to go finish his round. He just leaves. I was amazed at how cavalier Saul talked about his friends life. I’ll never forget that day.

Where are they now:
Hershel survived the blow. He broke a hip and never quite made it back to the course. He’d play a few holes here and there, but the accident effectively marked the end of his playing days. He died about 2 years later.

Saul, being a Holocaust survivor, was always was given a certain sense of honor and privilege at the club. The accident didn’t change that, but he did find it very difficult to find someone to fill Hershel’s place in the foursome. Saul is alive and still has a driver’s license.


Nothing too crazy. A couple short ones.

  1. A local bar had a Halloween tournament at the public course I worked at. They also had “employees” from the local gentleman’s club come out to drive around and serve drinks. They were all pretty sloshed obviously. Surprisingly no one was injured, but they did roll one of the carts down a 20 foot hill next to the 12th hole.

  2. Just a regular day and we get a call that a cart was wrecked. We go to check it out and the cart is 20 feet down a ravine, 3 of the 4 posts holding the roof are broken, GPS is 10 feet away, and the thing is done. Guy says he hit a wet spot! There is no way to put a cart in this ravine unless you are super drunk and or driving really fast at it and put it in there on purpose. The best part is that he stayed in the thing down to the ravine. Dummy could have gotten killed, but only had a sore wrist.

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Clear Eyes. Full Hearts. Can’t Lose.


Summer job in high school was working grounds at a local course…the superintendent, tired of working of 65-plus hour weeks, had me, a high school student, water the fairways by box. Mind you this was a public course and fairly busy so you had to follow the golfers up the fairway with the sprinklers so you were always just behind them and not delay golfers coming from the tee. Anyway, I punched in the wrong sprinkler head number and I completely drenched a foursome of old ladies. The sprinkler was literally two feet from the back wheel of their carts. I did not even realize what was going on until they started screaming at me. By the time I cancelled the sprinkler, their carts and clubs were soaked.

Almost 20 years later, I still remember them calling me an idiot and them driving away to tell the pro shop. Of course, nothing happened to me because the superintendent knew I was the only one on grounds that he could trust to properly water the course. Those women are probably dead now and I am still here…joke’s on them.


Ahh. The good old days of being a cart boy. My story isn’t very funny nor does it involve anyone that interesting, but it is stuck with me forever.

I was out managing the lot; assisting golfers coming into the club with their bags and cleaning clubs on 18. The pool was right next to the clubhouse, so you could see plenty of pool-goers coming in an out in their personal carts.

The son and his girlfriend of a notorious family at our club (30 years old+ and lived at home) were drinking heavily all day by the pool in the hot Midwestern son. They rip out of the pool area and start driving up the street back to their house - hooting and hollering the whole way.

For some crazy reason, the girlfriend decides to stand up in the cart while they are moving (keep in mind this is a personal cart so they have extra giddy-up). She turns around so she is now facing the back of the cart while standing up and hanging outside of the cart. She looses her balance, misses the “oh-shit” handle, and falls out of the cart smashing the back of her head on the pavement so hard that I could hear it from 100 yards away. Somehow she gets up and wobbles over to the grass along the back-side of 18 green - she did not look right. The guy is screaming bloody murder.

I hop in my cart and fly down there. This was my first time calling 911.

Come to find out, she ended up breaking her skull and blew a .31 when she got to the hospital. She wasn’t able to work or go to school for 12-18 months after the incident due to short-term memory loss. I will never forget the sound her head made hitting the pavement.


Here’s another…I grew up in rural Ohio so the county fair was a pretty big deal to my high school friends. I tagged along for an evening of fun, you know, a 17-year-old kid drinking Rumple Minz (100 proof) out of a water bottle walking around with his buddies talking shit to girls. Fast-forward to being dropped off at my house at 1 a.m. and having to be at the golf course for a 6:00 a.m. start. I am still not sure how I woke up for my shift but I made it to the course in a haze.

The superintendent drove me around in a cart and showed me specific areas he wanted me to hit with the rough mower. After showing me a couple of spots, we went back to the garage and he handed me a weedeater. He looked at me said, “Kid, I don’t think having you on a mower is a good idea right now.” Oops.


I spent my summers in college working in the bag room and caddying at a private club that was known as the top players club in the area - most scratch 'caps, state am champs, even a finalist at the US Am who went on to a middling tour career. They took pride in not giving any favors in the membership process, and one rule was that new members did not get full golf privileges immediately - they had to wait their turn for a full golf membership to open up and that meant they had to pay dues as “social members” who were only allowed to play Mondays, when the course was only open after noon, with no carts and occasionally some heavy maintenance going on.

During the time I worked there, one of the new social members also happened to be a local sports hero who had retired young due to some traumatic lower body injuries. He was beloved by fans as a tough competitor and is now in the Hall of Fame. The club seemed to take a perverse pride in showing him no special treatment, and he dutifully showed up to play on Mondays, often accompanied by famous teammates, and was never permitted to take a cart, instead forced to hobble around the course on his bum wheels.

At first, caddies jumped at the opportunity to take his loop, as everyone knew who he was, but one by one they began to beg off after learning how unhappy he was to be forced to walk and perhaps taking it out on the lads under the straps in the form of subpar pay and general grumpiness. By my second year there (still a social member), he was often relegated to hauling his own sticks.