Official Caddying Story: John O’Donnell

John O’Donnell is the founder of johnnie-O,  a branded lifestyle apparel company that embodies living your best life. The johnnie-O brand has come to define west coast prep and can be found in most of your favorite golf pro shops as well as upscale retailers, like Nordstrom and Bloomingdales. But long before he sought to redefine your wardrobe with inventions like the “Tweener Button” and even before he played golf for the UCLA Bruins, John found his rhythm by caddying at one of Chicago’s most esteemed golf clubs. He even earned a spot caddying in the Western Open and is still friends with his former caddie master, Steve Mocogni. Enjoy learning how caddying helped shape one of the great gentleman players in the game of golf.

At which golf course did you first caddie and how old were you when you started?

Bob O’Link Golf Club in Highland Park, Illinois when I was around 14 years old and probably weighed 110 pounds.

Why were you compelled to become a caddie?

We always had summer jobs, and it was a progression of sorts. At first, it was a paper route in 3rd, 4th, and 5th grade, then lawn cutting from 6th through 8th grade. But, around high school, I got the golf bug really bad, so I started caddying. The north shore of Chicago is loaded with great golf courses, and we were members at Exmoor Country Club. But I’d heard that Bob O’Link paid higher rates, so I went over there and signed up. For four summers, I’d caddie six days a week, making good money, like 35 bucks for a double bag. It worked out really well since I’d usually be able to hitch a ride or take the bus from Winnetka, where we lived. 

Take us through your first day on the job, who was your first loop?

Not sure about the first loop but I know that I was nervous. It was those golf bags, those seriously big, heavy leather bags. I swear I was probably carrying 80% to 90% of my body weight each loop. It was so bad that members would ask, “Can we help you?” I’d say, “Nope.” But when we’d get off of the 17th green and I’d give them the driver for the 18th’s tee shot, I’d go lean up against a tree in the rough, forecaddying. I remember thinking, “I’m just so glad this is over.” Those were some hot days in Chicago.

The caddie yard was also a good scene, a whole bunch of guys packed in there playing cards. You wanted to get out as soon as possible, but you also wanted to get the best loop that you could. So it was a dance. You didn’t want to get stuck with some jerk. To top it off, this was the golden era of tennis. Borg, McEnroe, Connors, Lendl and we’d all watch Wimbledon and the US Open down there. Everyone was into tennis. So sometimes you’d have Borg playing McEnroe into the 4th or 5th set, and it’s triple break point. All of the sudden, the caddie master calls your name for a loop, and you’re like, “I can’t leave!”

What was the biggest mistake that you made during your caddying career?

I can’t remember making any big mistakes, but I can tell you that I just tried to get out of the way when a player would get angry and lose it out there. One time, a guy choked a 4-wood and then started beating it into the ground before chucking it towards me. It was kind of intimidating, so I just tried to make sure that I didn’t get hit in those situations.

What did you most enjoy about caddying?

It was great to be around the game, making my own money. I liked the freedom and independence. I may have been 15 years old but looked like I was 11, so I just kind of shut up and did my job. But it was hard work. It was steamy out there during those summer days. 

Would you mind telling us about your experience caddying in the Western Open?

You bet, it was a great experience. This was back when the Western Open and The Masters were the only two tournaments where the pros couldn’t bring their own caddies. There was only one caddie representative from Bob O’Link, so it was a real honor to be chosen. But I was a hard-nosed, very dedicated caddie. I also played a lot and had a good relationship with the caddie master, which helped. After getting selected, they brought all of the caddies to the course, which was Butler National that year, so we could decide who was caddying for whom that week. It was a really big field, maybe 120 players, and they wrote all of our names on pieces of paper. Then, all of the pieces of paper were placed into the winner’s trophy (a big cup), and they drew names, like a draft. So the first name drawn got to pick any player in the field, like Tom Watson or Seve. My name, of course, was pulled around 106 of 120, so the pickings were slim. I glanced at the roster and selected the only name that I recognized: Larry Rinker.

Larry and I had an incredible time that week. He was a younger guy out of the University of Florida, and being inside the ropes with him was a privilege. He taught me how to read uphill yardages, as I lugged around his big McGregor bag, which was probably 70% of my body weight. He had this wooden Cobra Baffler that he’d just hit on a rope; I still think of him whenever I see one of those things in someone’s garage.

But “Rink” was a total party boy. He played guitar in Payne Stewart’s band. He was kind of a renegade, not in a bad way but edgier than the norm on tour back then. We really hit it off and were walking down the fairway during the tournament, when he said, “Check out those two babes over here along the ropes.” I looked over, and sure enough, the two girls happened to be my sisters! In his defense, they were totally cute, drinking beers in their Ray Bans. So I introduced him to them after the round, and everyone got along. My sisters were like 21 and 19 at the time, so they told Larry to join us at the 4th of July BBQ our family was hosting the next day. He came over to meet the family, and we were drinking beers. I thought to myself, “This guy really loves me,” not realizing that he was only there to chase my sisters. At the end of the night, my sister, Julie, and I drove Larry back to his hotel near Butler National. We got there, and I still didn’t fully catch on when he told me to go through his golf bag and pull out anything that I wanted, while he said goodnight to my sister. So, I’m pulling out gloves and balls, happy as can be. Meanwhile, Rink was just trying to isolate my sister for a make out session!

Later when I attended UCLA, Larry would call me up when he was in town to play the LA Open. One time, he borrowed his friend’s red Ferrari, and we zipped around Westwood while he was maybe even burning a joint. I remember thinking to myself, “What am I doing here!?!”

Forty years later, we still keep in touch. I just talked to him three months ago. He has a great family and very successful kids. He went on to enjoy a very long PGA Tour career and is now a golf instructor, splitting time between Florida and Colorado. He even has a show on Sirius XM radio.

Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?

Well, I caddied for Elroy “Crazylegs” Hirsh, but he was probably before your time. There was a funny situation where I was dating this gal but not to the point that I’d met her parents, and her dad was a member. So I was looping for him one day and had actually been hanging out with his daughter the night before, doing our thing. I remember thinking, “oh, if he only knew.”

I remember caddying in the big member-guest, called the Hullabaloo. We got free food, like oranges and cold plums. I was so psyched. You’d meet all of these different guys and hear great stories, as well as some off color jokes. You saw a whole new dimension to the adults, some of whom you’d known your whole life. I guess it’s a lot like guys caddying for us now!

For johnnie-O, specifically, there wasn’t really anyone who opened doors since it got started so many years later. It’s not like, as a 17-year old kid, I could say to some guy, “Let’s keep in touch,” and social networks didn’t exist. But I will say that my caddie master, Steve Mocogni, helped me get out on the course when I’d visit Chicago and would swing by the booth in Orlando. He’s the best and is now the general manager of Bob O’Link. But, he teased me about my sisters, too. He’d say, “O’Donnell, get your sisters up here to pick you up, or you’re not getting out today!” I’m like, “OK, Mac.” 

What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?

Just the work alone was a big lesson, honestly. I had to play through a lot of pain, so to speak, with those heavy ass bags in 92 degree heat. I hate to play old man, and I was very fortunate to come from a nice, upscale community. But it wasn’t even a question if you were getting a summer job. We all worked. From the paper route to cutting grass and then the caddying, we all gained a lot of discipline from working.

The other thing that you learned was about different personalities. I was more in-tune with and admired the gentleman player, not the pricks with bad tempers who maybe thought they were better players than they actually were. 

If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?

Oh boy, let me get back to you on that one. There are some great stories out there, and I’ll try to get you someone good.