Tales of the Shirtless Caddy

The Friday sun hangs lower now, but it still carries the warmth of August. It’s the last workday before the long weekend, the final stretch of summer where a polo and khaki shorts feel like a uniform of freedom. Out on the course, the air is still light, and the fairways are a touch firmer than when fireworks exploded overhead. You walk without hurry, soaking in each step as if the season itself were trying to linger. By Tuesday, life begins again in its familiar rhythm. But today, in this penultimate twilight round, summer remains.

If you want to bring your own caddy to a tournament, choose the right one. Upon further reflection, my 3 loops around Meadow Brook at the Met Open led me to a single conclusion - picking the right caddy is critical if you want to play well. Below is a true story of when I did not heed this advice. Enjoy.

When I was 17, I played in a city junior event; a one-day, 36-hole marathon. I probably should have carried my own bag, but after getting stuck with a poor pairing, I decided to call my friend Hunter instead. He and I were close, and he played on our high school golf team, though I wouldn’t exactly call him a golfer. He wasn’t the most polished guy, but he always managed to make me laugh. In my mind, that made him the perfect caddy.

Anyway, he was a (hilarious) disaster. Looking back, I made a few critical errors:

What did I expect bringing this kid to carry my bag for a 12 hour day? He had no idea what he signed up for. He didn’t know where to place the bag, where and how to walk on the greens (He walked in my competitors lines more than once). I had to teach him how to do the job on the fly. That’s not what you want when you’re playing a stroke play medal event!

As an aside, I was never super competitive in these events. I just wanted to post some reasonable scores in the mid to low 70s to help squeak my way onto a college team. Hunter was actively hurting my chances with each passing hole.

We completed the first 18 in about 4:30 (without any major hiccups) and took a break for lunch. We stepped back out to the 10th tee in the brutal July heat at about 1pm.

I wasn’t super focused on his physical state during the second 18. How could I be? He seemed content with his 2 tins of Grizzly Wintergreen (longcut, he berated anyone that dipped pouches, and this was wayyy before Zyn existed), and I was grinding 4 footers just trying to break 80.

I bring this up because he didn’t drink a single sip of water all day, and on our 30th hole, he hit the wall.

First, he wandered off in the middle of the hole to find water, and returned at the next tee box without his shirt on. Yep, he went tits out, only the caddy bib up top. I think he took the shirt off because he was partially delirious/hallucinating but also because he was fairly sure that taking his shirt off on a golf course was an OK thing to do. Truly remarkable.

Imagine this, a scruffy, pudgy, 5’9 kid with nothing on but a caddy bib, white-rimmed Oakleys, an orange Rickie Fowler Hat, cargo shorts and sneakers. To say it was breathtaking wouldn’t do it justice. Not even AI could recreate what we witnessed that day.

He then went and laid down, fully horizontal on the forward tees of the next par 3 and chugged water.

I carried my bag for the final few holes as he walked alongside me, like a dad walking his son to the first day of school.

You’ve been planning a golf trip with a group of your best friends for the past few months, and it’s now the night before, so what do you pack?

For the sake of this post, let’s say you’re flying out on a Thursday night and plan to return Sunday evening. That gives you three days of golf and two nights of going out. Now, what you wear will be largely dependent on where you’re traveling. Let’s say you’re headed out west to play Bandon.

To start, invest in a nice carry case for your clubs. Alternatively? Pay for ShipSticks if you don’t want to check the bags. It’s a pretty good product.

Please don’t go to an airport without a proper carry bag for your clubs. Do not use the rain gear cover for the top of your bag as the only protection. Best case? Something gets stolen out of the bag. Worst case? Multiple clubs break in transit. I suggest a Club Glove.

Ok, now that the clubs are protected, lets jump into what you can’t forget. Depending on how good a player you are, bring at least 9-12 golf balls. You don’t want to be spending your pro shop allowance on boxes of balls halfway through the trip.

Other items I suggest packing:

Ok, on to the clothes. The goal is to not have to check a bag. I dropped a few weekender bag recommendations (Filson, Halfday) in this post What to Wear this Fall. Those should be easy enough to carry onto a plane. Ok, onto the clothes.

For a trip like Bandon, or any trip up north in the fall, you’re going to want to layer up. I always suggest the layering pieces from Holderness, Peter Millar, and rain gear from Kjus. I tell people to buy from the same one/two brands for this reason: interchangeability. You can blindly grab 4-5 shirts, a few vests, and a sweater and not worry about mismatching patterns or clashing with vibrant ugly colors. This simplifies things, especially when you don’t want to spend a ton of time thinking about what to wear.

Note - I’d suggest packing one pair of golf shoes and 2 hats max to save space. Unless there is rain in the forecast, it’s not worth packing a second pair.

Once you’ve settled on golf clothes for the rounds, I’d pack a few nice button down shirts, some brown loafers, (Shoes for the Modern Gentleman), and a nice belt for the night(s) you decide to go out.

Enjoy the trip!

The Pro Shop is not somewhere to act like a kid in a candy store. I have seen the discourse on Twitter, and will lay out what I believe to be a common sense approach to acting in a pro shop as a guest:

Act like you’re a member.

Would a member of their home club walk out with an assortment of 10 different articles of clothing and 3 head covers? No way. Accounts like “Pro shop bucket list” or whatever it’s called glorify this low-class behavior as if its gospel. Hopefully this publication has given you some insight into how to properly act like a member, and steered you away from this reproachful trend.

Talk soon,

BTG

Email me: [email protected]

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