Official Caddying Story: Jack Druga

Jack Druga is the head golf professional at one of the world’s most distinguished courses, Shinnecock Hills Golf Club. He was previously the head pro at the Country Club of Fairfield and The Creek Club, but it was caddying as a teenager in Pittsburgh that first introduced him to the game. An advisory board member of both Titleist and Peter Millar, Jack has done just about all there is to do in the game, including helping guide Tiger Woods around Shinnecock for 36 holes leading up to the 2018 US Open. He not only supports the game as a member of the PGA of America but also through the Metropolitan Golf Association (MGA) and on the board of the Amateur Golf Alliance (AGA).

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

Oakmont Country Club when I was 14 years old.

Why were you compelled to become a caddie?

I was more into baseball as a kid, and we weren’t members at a club. But my dad would take us out on a par-67 course, called Schenley Park, that was walking distance from our house. It was as public as it gets: pull carts, no bunkers, artificial turf tee boxes, and a mix of kids and older retired guys who’d also play cards in the clubhouse. It was next to Carnegie Mellon’s campus and is still there today.

Then, in 1973, the US Open came to town, and my dad got us tickets for the last round when Johnny Miller shot 63. I had never seen anything like Oakmont. It was pristine. On top of that, you had Jack Nicklaus, Arnold Palmer, and Lee Trevino all in contention. I found out that I could caddie there when I turned 14, which would be the next year, so that’s what I decided to do. The money didn’t even matter; it was the fact that I could play the course on Mondays. The chance to play Oakmont, are you kidding? I played until dark, sometimes 40 or 50 holes in a day. I basically just played until I got picked up. We made between 7 and 10 dollars a bag, but that wasn’t much of a factor until I got a little older and wanted to save up for a car. That’s really how I got started.

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

It’s pretty crazy because my first day as a caddie occurred during Bob Ford’s first year as an assistant, working for Lew Worsham, the longtime head pro and the 1947 US Open winner. Fast forward to today, Bob’s my best friend and was the best man in my wedding. At the US Open in 2018 at Shinnecock, I’m the head pro, and he’s the starter. I said to him that it would be impossible to imagine that happening back in 1974, when I was 14, and he was 21. We were just so happy to be at Oakmont.

That first week caddying, the caddie yard was pretty unique. The steel business was still going, and most of the caddies were older guys who also worked in the river towns. They would work the night shift and then come straight to the club to caddie. After the loop, they’d get some rest and go straight back to work. It was intimidating. Those guys were intimidating. I remember thinking “You guys are working all night and then coming up to caddie. When are you going to sleep? What do you do for fun?” Those guys weren’t caddying as a summer job; they were caddying to pay the bills and feed their kids. Talk about work ethic, it was a really interesting group, and you had to earn your stripes. But my dad was a boilermaker, a hard working strong work ethic guy. I learned a lot from them.

There were some kids caddying but way more older guys. The caddiemaster was a scary old guy, Joe Stoner. After my first couple of loops, he liked me and started to give me better loops. You know the drill. You start out with the ladies, two 36-handicap ladies. They see how you do, and I worked my way up. It didn't take long for me to become a regular guy, and I got out everyday. Oakmont was caddie heavy. Everyone walked. There were only 5 to 10 guys who had to play in carts. The members were working people. That’s Pittsburgh. The guys playing during the week were retired. That’s what I remember about my start, actually broke in pretty quickly. 

I caddied for five years, even caddying for Bob in section events back then. I went on to win caddy of the year in 1977, and there was a big banquet and even a trophy. There was no voting or anything; the caddiemaster just picked a guy. But I remember getting 150 bucks for merch in the golf shop.

What was it like working for Lew Worsham?

He was great, an old school guy. Lew soon asked me to work the range, after caddying in the morning. He said, “You’re here everyday. Why don’t you pick the range afterwards, so you have a place to practice?” He knew I had no place to practice. The course I played at had no range. So he gave me this job and even paid me in cash. I’d bring him the money, and he would never even count it. He just said, “You take half and I'll take half.” No time cards. No paychecks. 

The range job helped a lot. I was able to hit balls every day. I was chipping and putting at Oakmont for god sake! I became a pretty good amateur in the area and wound up going to Florida International University on a golf scholarship. Even though we were DII, we played a lot of great players, like Mark Calcavecchia, Paul Azinger, John Cook, and Jodie Mudd.

When the 1978 PGA Championship was held at Oakmont, the range job took on a whole new meaning. It was the biggest week of my life, getting to see all of the Tour players up close. It was eye opening. You saw not only how good they were but also how they treated people. Tom Watson, who wound up losing in a playoff, was amazing to us. I’ll never forget. He was leading after the third round, where there was a lightning delay, so he finished in the dark. He did his interviews and then all the sudden, we heard metal spikes walking toward us. It must have been 10 o’clock at night, and frankly, we were having a couple of beers after a long day working the range. It’s Tom Watson with his glove on and a 7-iron in his hand. He said, “Can I hit a few balls? I know you’re closed up, but I’d appreciate it” The range was completely dark, so he took his bag of balls over to a grass patch near a street light in the parking light. He must have hit 30 or 40 balls and then gave us 100 bucks! He said, “Thanks, I know you probably wanted to go home.” If you don’t think we were rooting for Tom Watson the next day! How impressive, the dedication, it was a pretty good Saturday night story.

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

No, I’ve never made a mistake. Just kidding! There was one instance that stands out. I played tournament golf, so I was psycho about counting the clubs while caddying at Oakmont. I was working for a guy in the club championship, and I swear I counted the clubs. But sure enough, we get a couple holes in, and there’s an extra wedge in there. Maybe it was under the towel. Maybe I was nervous. I have no idea. There may have been others, but that’s the only one that I blatantly remember since there’s only one thing that I needed to do before we teed off. I can’t remember if we lost the match or not. Probably lost and I'm trying to forget!

What did you most enjoy about caddying?

I just loved everything about it. First, it was Oakmont, the bunkers and the beauty of the place. Back then, there were trees everywhere; it was almost getting unplayable with the trees. But it was a big, perfect grass park that was great to walk. I also enjoyed the banter between the people, watching the guys bet. I was able to learn about golf when caddying for the good players, which helped with all of the competitive golf that I was playing. As caddies, we were treated very, very well, by the members and the golf staff. 

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

My regular loop was a working guy, named Gene Farrell, who was in the food distribution business. He was a past club champ at Oakmont but actually grew up playing the same little public course that I did. He knew where I was coming from because that’s where he came from. He even knew my father. I was usually out with him when he played. I picked up on a lot of little things from him, how to treat the members, staff, and caddies.

The Oakmont members all treated me great. In 1977, I qualified for the US Amateur at Aronimink as a senior in high school, but I didn’t have enough money to play. The members passed the hat and raised a couple thousand dollars for me to compete. It was more money than I could even spend. They were so generous. Once you were part of the family, they took care of you. I qualified again two years later, and they did it again. 

The Tour players I caddied for also made a huge impression, like Arnold Palmer, Jack Nicklaus, Greg Norman, and Lee Trevino. I got to caddie for Norman in the early 80s when he was the top player in the world. It helped you understand what good really was. I was so stupid that I thought I was good! I later got to play with both Jack and Lee. Jack was my idol growing up. Caddying for him and how he treated me, he made me feel at ease. Arnold was the same way. Trevino was not as interested in me but amazing to caddie for him because of how good he was.

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

The way you treat people and the work ethic, especially those steelworkers in the caddie yard.

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

Jimmy Dunne, he’s an unbelievably interesting guy and caddied at Southward Ho on Long Island. We’ve played a lot of golf together. Nobody is more generous to the caddies and staff, and he was heavily influenced by the guys that he caddied for, especially the ones who would let him get anything that he wanted at the snack bar. With some guys it was just a soda or a candy bar, Jimmy wanted to be like the guys who told him to get whatever he wanted. 

He says that he can tell within two holes of playing with someone if he was once a caddie. How fast they play. How they treat the caddie. How they handle themselves. And he's usually right. He’s so successful and such a golf guy, but he relates to the guys who caddied as a kid. I think he lied about his age to get the job, and that got him started in golf.

Know another great caddying story? Enter their information below:

Kai Sato

Kai Sato is the founder of Kaizen Reserve, Inc, which exists to foster innovation and unlock growth. Its primary function is advising family offices and corporations on the design, implementation, and oversight of their venture capital portfolios. Another aspect is helping select portfolio companies, both startups and publicly-traded microcaps, reach $10M in revenue and become cash flow positive. Kai is also a General Partner of Mauloa, which makes growth equity investments into cash flow positive companies; an advisor to Forma Capital, a consumer-focused venture firm that specializes in product-celebrity fit; and a fund advisor to Hatch, a global startup accelerator focused on helping feed the world through sustainable aquaculture technologies.

Previously, Kai was the co-president & chief marketing officer of Crown Electrokinetics (Nasdaq: CRKN); the chief marketing & innovation officer of Rubicon Resources (acquired by High Liner Foods); a board member of SportTechie (acquired by Leaders Group); and a cofounder of FieldLevel. He’s the author of “Marketing Architecture: How to Attract Customers, Hires, and Investors for Any Company Under 50 Employees.” He has been a contributor to publications like Inc., Entrepreneur, IR Magazine, Family Capital and HuffPost; he has also spoken at an array of industry conferences, including SXSW and has been quoted by publications like the Associated Press and The Los Angeles Times. He is also the board chairman of the University of Southern California’s John H. Mitchell Business of Cinematic Arts Program. Follow Kai on LinkedIn or Twitter.

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