The Caddie Diaries: Round One

The first look into my experiences as a caddie…

Like most kids about ready to graduate college, I had no idea what I wanted to do with my life. Like every other college golfer, I had always aspired to turn pro after college, but under the circumstances I had no intentions of making a run at the mini tours. 

To my surprise, a friend of mine landed a job at a real estate firm in LA. I had been to California a couple times to golf before, and had always dreamed of living there one day. He convinced me to take a leap, and about a month before graduation I decided I was going to move to LA and search for a job. 

I got to LA, and finding a job was a lot harder than anticipated. I guess a degree from a mid-major school in Indiana didn’t mean much compared to the UCLA and USC degrees. I had heard caddying may be lucrative in LA, so I thought I might do that for the time being to earn some cash while I look for a job. I soon made a call to one of the more exclusive clubs of LA and was asked to come out for an interview. After my interview, I was given the green light to caddie. I’d have to go through some training rounds with the assistants first, but I was good to go. 

After my training rounds, I sat around the caddyshack for a couple of days before I got work. I loved the caddyshack. It consisted of people from all over the world, and all nationalities. We had actors, comedians, teachers, aspiring writers, waiters, lawyers, and college kids. There was always something special about sitting down in the caddyshack and shooting the breeze with the guys. I felt like you could learn so much from each guy about life or golf in general. One of my favorite lessons learned was, when you’re a caddie, you don’t have to be a golfer. I thought I was probably hot shit being a former D-1 golfer coming down to caddie, but some of our best caddies couldn’t hit a ball 100 yards. Each of the top guys seemed to know the course and game like the back of their hand. Each break and each slope, like they had sat there and studied it for hours. I was proven sooo wrong.

Then I got the call up to the first tee…

I got to the first tee and found out my first loop was going to be singling in a group of 5 (one other caddie did a 4-bagger). I got to the tee and started shaking hands with a couple of the group members. I always believed the old rumor of how a nice firm handshake is important. As I was shaking hands, I came across a guy who I felt I barely gripped his hand. I thought, “Shit. Here we go. First loop and this guy already thinks I’m a weenie.” At a second glance I realized this guy was huge, and not just a normal guy because I sort of recognized him, but who was it?

Everyone teed off, and we were on our way. Walking down the fairway with my guy, I found out he was the QB at UCLA during the 60’s. He would go on to be one of my favorite loops, and all around one of the friendliest guys at the club. A couple holes later I found out another member of our group was the Vice President of Marketing at Travis Mathew, and his dad, who was playing with us as well, was gold medal winner in volleyball in the Olympics and also volleyball play-by-play guy for NBC. I was in awe of my surroundings, and I was sneaking texts to my Dad at every chance I could to ask if he knew these famous guys I was around. Just a kid from a small town in Indiana, and now I’m rubbing elbows with these guys?! But who was that big guy?

So, I finally had to ask. Walking up the long 12thfairway I asked who that guy was in our group. My guy said, “Well, you’ve probably heard a lot about his story. He just had a documentary come out on ESPN a couple of months ago, but I met him and was really inspired by what he’s done, so I invited him out.” It was Ryan Leaf. All the crazy stories I had heard, and all the news stories I had seen, but he was honestly such a joy to caddie for and a real good dude. Plus, if he gets ahold of one off the tee… so long ball.

In one of my favorite memories of caddying, I had made an effort all round to make sure I shook Ryan’s hand well on 18, after flubbing on the first tee. As everyone putted out on 18 and I went to shake his hand, it happened again. This time I realized it wasn’t my fault. I was afraid that I wasn’t giving a firm handshake, but his hands were just that BIG that I couldn’t even get my own hands around them. It felt like I shaking a giants hands. Like I was a baby trying to shake a grown ups hands.

This story probably sounded better in my head then how it came out, but that was just round 1. I have so many great stories to share and some that I won’t, for private reasons. Caddying for that year of my life was one of my best life experiences so far, and one that I’ll never regret doing. I met a lot of great people who I felt will help shape my future self, because I saw a lot of people who I wanted to be like, and a lot of people who I didn’t want to be like. I look forward to sharing those stories with you with time.


Published by golfcourseraterguy

Sports fan with a passion for golf, basketball, and the Chicago Cubs.

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