The singular place caddies hold in the game, the shepherding of players while serving both as psychologist and collaborator, is one with no real equivalent in sports. Golf rightfully celebrates this, particularly the star tandems and the journeyman loopers who have become known by nicknames such as Fluff, Socks, Bones, Pepsi and Killer – but it’s not the full story.
We tend to forget the intrinsic value of caddying itself, letting it float in the back of our collective golf consciousness. Kai Sato (above, right) wants to bring it to the forefront.
Back in February, Sato founded the site Caddyshack to Corner Office in an effort to tell stories of successful people who learned vital lessons through caddying. That list is impressive both in length and caliber, featuring noted golf course creator Mike Keiser, Linksoul founder John Ashworth, johnnie-O apparel founder John O’Donnell and some of the most creative minds in and out of the industry.
Sato’s growing catalogue of caddie narratives has given these reputable figures an opportunity to explore why their experience affected them so deeply. No matter how many years they are removed from running after divots or discerning the amount of grain in a green, that passion comes rushing back with nostalgia.
“It transports everyone back to this transformative time in their lives,” Sato said. “You are in your early teens or maybe early 20s when you’re coming of age and gaining a lot of independence. People have gotten emotional talking about it. They’ve come an awful long way in their lives and caddying was kind of the genesis for them.”
The concept of telling caddie stories came to Sato long ago, but the final push to publish them arrived after the tragic death of NBA legend Kobe Bryant on Jan. 26. Sato wasn’t necessarily a diehard fan, but after watching the Los Angeles Lakers’ tribute video celebrating Bryant, he found himself motivated to put in the work to tell these tales before it’s too late. When former General Electric head man Jack Welch – who grew up caddying at Kernwood Country Club in Salem, Mass. – died on March 1, it only added urgency to the project..
“I was telling my friend recently that I remember ditching one of my accounting classes to caddie for Jeff Brotman, the founder of Costco. I didn’t want to listen to an accounting professor talk about how a balance sheet is going to balance, I wanted to talk to the guy (who) did it.”
The messages from former caddies-turned-CEOs and others who have used the looping experience to bolster their understanding of the world was too meaningful for someone not to share them openly.
It’s a natural fit given Sato’s background. While attending business school at the University of Southern California, he became enthralled with caddying in the summers at Bel-Air Country Club, carving out an added significance in his life.
“I grew up a lot of my life without my father around and I got to spend time with all of these really interesting, successful people in different cross-sections of the world who became mentors,” Sato explained. “I was telling my friend recently that I remember ditching one of my accounting classes to caddie for Jeff Brotman, the founder of Costco. I didn’t want to listen to an accounting professor talk about how a balance sheet is going to balance, I wanted to talk to the guy (who) did it.”
Sato used that experience to grow a career as an investor with an affinity for building companies. Seven years ago, he joined Bel-Air as a member himself and remains close with those in the caddie program at the facility.
Throughout his time in the business world, Sato kept coming across former caddies who had grown to incredible heights. He pitched the idea of telling their stories to others, but ultimately he took it upon himself to “put the jersey back on” and create Caddyshack to Corner Office.
What shines through immediately is how each of these mentors gained empathy from their caddying experience. In a recent piece featuring Bill Doyle, the former chief executive officer of the Canadian fertilizer conglomerate Nutrien, he expressed how making a mistake while caddying for Arnold Palmer taught him an imperative lesson.
“We were on the 12th hole, a par-3 that was 195 yards,” Doyle said of his experience caddying for Palmer at Bob O’Link Golf Club north of Chicago. “That day, it was played dead into the wind, and the pin was all the way back. It was really gusting, probably a two-club wind. He had a fabulous round going so far, and he’d ask me what club to hit since we’d been out together before. He knew that I knew the greens and how to caddie, so there was some trust established.
“It was 195 yards, but I told him it’s got to be playing 220. He said, ‘I can get a 3-iron there.’ I said, ‘I think you’ve got to hit the 2. It’s really gusting, with the pin all the way back.’
“He steps up and smokes a 2-iron right at the flag. It flew the green, leaving him short-sided coming back and chipping downhill. He takes his only bogey of the day. I was devastated. Walking to the next tee, I said, ‘Mr. Palmer, I’m so sorry. I thought the wind would knock that down.’ He put his arm around me and said, ‘Hey, don’t think that way for a minute.’ Despite that lone bogey, he shot 66 that day.”
Doyle went on to explain how golf and caddying are character-revealing, so much so that he would ask to play golf with a company’s CEO when Nutrien was examining a purchase.
Sato’s ultimate goal from reaching out to Doyle and others is to give this community a voice few have heard, which perhaps could inspire others to pursue caddying. He has identified seven billionaires who grew up caddying, and the network within the golf industry is robust. It’s said that a good caddie always leaves his player with a positive thought before each shot; Caddyshack to Corner Office hopes to be the embodiment of that virtue in written form.
Sato has formed natural alliances with the top caddie organizations in the country. He credits Bill Kingore, the senior vice president at the Western Golf Association and Evans Scholars Foundation – the nonprofit group that provides full tuition and housing college scholarships to around 1,000 caddies at 18 universities – for being instrumental in the venture.
“Kai is a superstar who believes in caddying because he was one,” Kingore said. “The Evans Scholar Foundation has had 11,000 alums and given over $400 million of scholarships beginning in 1930. We really believe in the lessons learned in the caddie yard, so it naturally led to Kai and I becoming friends.
“In our program, we have many, many examples of people who have gone from that yard to the corner office. People like Tom Falk, the former CEO of (manufacturing company) Kimberly-Clark who was an Evans Scholar who went to the University of Wisconsin. People like Sam Allen, the former chairman and CEO of John Deere who went to Purdue. Being able to share stories from people like that will open a lot of eyes.”
The aim of stories at Caddyshack to Corner Office is not only to show what can be accomplished, but also to describe the origins. In Kingore’s mind, that’s the most important aspect of all.
“Being able to caddie as a youngster is really like having a four-hour internship,” Kingore said. “It’s learning when to speak, when not to speak, how to act around adults, learning about people you want to emulate or don’t want to emulate … ”
All of it is valuable in the moment. Passing along those lessons may be even more valuable.