Dos and Don'ts

9 things I wish I knew before caddieing in a serious event

This is a big time of year for qualifying events. There are few events bigger than the U.S. Mid-Amateur, and last week I had the pleasure of caddieing for a buddy, Curtis Loop, who is a former colleague of ours and probably the best golfer I’ve gotten to play with (including pros and former tour winners), in the qualifier at Knickerbocker Country Club in Tenafly, N.J.

I knew he had a great chance, and I was incredibly nervous with the serious stakes: Curtis is a member at Sleepy Hollow Country Club, which is the host of the U.S. Mid-Am this year, so this was a qualifier he had circled for years. To set the stage further, Curtis was an accomplished junior player in the area then played at Cal, when current pros like Max Homa and Brandon Hagy were there, before finishing his career at Georgetown.

/content/dam/images/golfdigest/fullset/2023/8/hennessey-curtis-loop-caddie-qualifier.jpg

The player in this group is to your right.

Though Curtis missed out by one, we had a great day—and I left thinking that there were a few elements of the day I wish I had thought about beforehand. I'll list my biggest takeaways below. I hope these things help you the next time you get asked by a buddy to loop in a qualifier with stakes on the line.

Be really good at raking bunkers.

Let's be honest, there were few things I was actually responsible for on the day. This was one of them. Do it poorly, and you might negatively affect competitors behind.

If you’ve never been taught the proper way to rake a bunker, try to pick the brain of someone who caddies or used to caddie at a club. The way it was explained to me is that work on the rake until everything is as smooth as when you entered. You might use the opposite side of the rake to smooth out the sand, depending on the type of sand used at the course. Whatever you do, don't leave any footprints—and double check you didn't miss anything.

It sounds silly, but cleaning golf balls is probably the most important thing you’ll do.

I took this one for granted. No, it ain’t too hard to clean a golf ball … but it does require a wet towel and some elbow grease. Make sure you bring a towel and keep it wet throughout the round. If it resorts to doing a spit shine on the golf ball, you gotta do whatever it takes to get the dirt off the ball.

Knowing exactly the type of things your player wants to hear can be crucial.

Be mindful about exactly what motivates your golfer. There’s nothing like hearing the wrong thing right before you’re about to address the ball, such as “remember, there’s OB left” right as he’s addressing the ball. If you feel your player needs to know something, make sure it’s at the beginning of when they’re starting to strategize. Last-minute advice should be simple as: “OK, put a good swing on it,” or “you got this.”

Curtis isn’t a very analytical player when it comes to data and all the green-reading stuff. I showed him the StrackaLine app the day before, and he quickly looked but handed it back to me—explaining that more important to him was taking his mind away from the grind of competition in between shots. My goal for the day was to treat the down time in-between shots just like any other round, chatting it up with a buddy.

Do some scouting on the greens.

I caddied for Curtis at a course where I was fortunate to be a junior member for a few years. So I came in knowing the general breaks and tricks to the greens. But even better was getting out there for a practice round the day before, and there was a tiny red spray-painted dot on each putting surface where all the pin positions would be located the next day. That allowed me to do some advance scouting on the specific spots on the greens. That level of preparation made me more confident entering our qualifying round.

If you want to go above and beyond, make a conforming green-reading book.

If there was one thing I wished I did, I wish I had either prepared a handwritten green book based on the specific pin positions we saw the day before. I could’ve created a makeshift drawing for each green with the general breaks. Or, you might find a website or an app that has mapped out all the undulations (StrackaLine is a great one) and print it off to use. (Just double check the dimensions are conforming with USGA rules.)

Bring a caddie bib.

/content/dam/images/golfdigest/fullset/2023/8/curtis-loop-hennessey-caddie-qualifier.jpg

I underestimated the value of a caddie bib, but I was so glad I had one, thanks to my guy Bryan, another caddie at Knickerbocker who happened to have two bibs! You’re constantly juggling so much stuff the entire day—a rangefinder, a towel, tees and a divot-repair tool, water bottles—essentially anything your player asks, and you can't push back. I would’ve looked like a baffoon trying to balance that all amidst my two shorts pockets, so if I were to caddie again, I’d definitely invest in a caddie bib. Plus, they made me look official.

Know the details of the facility.

Curtis started on the 10th hole, which is a solid 10-minute walk from the practice putting green, or a two-minute golf cart ride. So he made sure to be done practicing 20 minutes before the tee time. Golfers are creatures of habits, so Curtis found it helpful to know the day before that he should build in an extra 10 minutes into his routine for the trek over to Hole No. 10.

You need to be very clear with your advice—and if you don’t have full conviction, let that be known.

Again, an area I struggled with. Though I’ve observed hundreds if not thousands of tour pro-caddie interactions, I’m not assertive in general. I could’ve stepped in and disagreed with Curtis on a few decisions, but I also knew that this was his qualifier, and I was mostly just an observer. Still, I could’ve been clearer about my knowledge of a few greens and how I knew they tilted. And a few times, he asked me if I liked a particular club off the tee, and I could’ve voiced my opinion a little clearer. Next time I’m in this position, I’ll be more decisive with my advice.

Conversely, I think it’s also important to make it clear when you’re not sure about something. If the player takes your advice and it was wrong, but you didn’t make it clear you were just using an educated guess, then that’s on you.

Know before the round, whether or not your guy wants to know where he stands.

We talked about this the day before, so I knew that Curtis didn’t want to look at the leaderboard at all. I decided I wouldn’t either, knowing that maybe something I said or my attitude could give him a clue as to where he stood.

It turned out that it was a little slower on the last two holes, and I was looking at text messages from friends who are asking for updates, so I did end up looking for at the leaderboard over the last two holes and had a feeling he needed a birdie on one of the last two holes. I think I did a good job at concealing the info, but if I wasn’t as subtle, this could’ve really affected his mind-set. Make sure you guys are on the same page.

Bonus tip: Stick around till the end.

Especially if your player is in the afternoon wave, have a nice cold drink and wait for the last groups to come in. There’s something satisfying about being there for closure after the emotions you’ve put into the day. Curtis did have to hang around until the end because there was a chance there’d be a playoff for an alternate spot, which didn’t come to be, but we were still happy we hung around to talk to fellow competitors and get that sense of closure.