Longtime Player, First-Time Looper
- Updated: August 24, 2026
I stood there in awe with a Callaway staff bag slung over one shoulder and a damp towel draped over the other as John missed wide right for his fifth three-putt of the day. It didn’t even come close to touching the hole.
I had spent the last seven years working the carts and the bag room at a private club.
A job often conflated with caddying by those outside the business. But it’s not the same, and it really isn’t even close.
In the bag room, we got the members ready for their round. We got their clubs out and set up on a cart if they were riding. We made sure the carts were charged, clean, and stocked with all the essentials: towels, tees, scorecard, pencils, divot mix.
When they finished their round, we greeted them with a smile whether they deserved it or not. We unloaded the bag onto the bag rack and cleaned their clubs. The quality of the clean typically depended on a combination of tip amount and whether or not we actually liked the member.
We had little involvement in anything in between the first tee and driving off the 18th green.
I would come to find out that caddying was very much the opposite.
John was a long-time member of the club.
He had been there long before I started working there, and probably before I was born. He was in his mid-sixties and a really solid golfer from what I could tell. We always had a good rapport – he was one of the ones that got a full brush and water bucket clean no matter what he tipped. He was one of the good ones.
So I suppose I shouldn’t have been surprised when he approached me one day with a proposition. He was playing in a Connecticut state amateur tournament and needed a caddy.
I was about 23 years old and had been playing golf seriously for most of my life. As a kid I would spend entire days at the local muni in the summer, getting dropped off by my mom on the way to work and picked up on the way back. I loved everything about the game and was certain I would knock this out of the park. I agreed to the job with full confidence that I’d be fast-tracked to becoming the next Bones.
The event was at a high-end private club in southern Connecticut. The drive down was long and awkward as we each mentally prepared in silence.
Within the first three holes, I caught on to his yardages.
He was about three clubs behind me, but knew exactly where it was going. That was easy enough to remember. I was amazed at how consistent he was and how easy he made ball striking look.
Mostly I carried the bag. I helped him pick some clubs and gauge the wind. I helped read some putts and made sure there were no women in the vicinity while he took a leak next to the tee box.
Then the first three-putt came. He missed a two and a half footer after a good lag from about thirty feet. Then again on the next hole. And the one after that.
As the caddy, I couldn’t help but feel partially responsible. He did call me in on the reads and they were mostly wrong. But still in my young, naïve mind, I felt like I would have drilled every one of those shorties he missed.
I started wishing I had brought a gray wig and a fake mustache with me so we could pull off some kind of switcharoo on the walk up to the green. Maybe I could distract the other guys in the group and hit the putt real quick while they weren’t paying attention. Anything to stop this.
We missed the cut by a mile and drove home in even more silence than we drove there in.
But this time I was thinking about how caddying wasn’t for me.
I am simply too engaged in the round and all I want to do is play. I want to hit putts. I want to hit chips. I want to hit driver so we could get it within 30 yards of the guys we were playing with, even if it’s not in play. It was painful for me to watch and help someone else play, even if he would beat me by 10 shots straight up on any given day.
Since then, I haven’t carried another person’s bag on the course. I grew up to three-putt five times in a round on my own. To take a leak in the trees keeping a lookout over my shoulder for a rogue beverage cart. To silently blame caddies for missed putts and misjudged yardages.
It turns out I was never meant to become Bones, but instead was meant to become John.
Two Inches Short is a place where amateur golfers can unapologetically be themselves. It’s where we can all relate to the greatest game ever played at a level we can all understand.
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