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What A Caddie Learns About You Just From A Handshake

What A Caddie Learns About You Just From A Handshake

Your caddie does so much more than carry a bag — they’re more like your personal shrink for the day. To learn more about how they read minds, Connor Laubenstein went to Bandon Dunes, the Mecca of American caddying, and played with one named Squid.

Connor Laubenstein

In the caddie shack, praise is often the mere absence of criticism. But at places like Bandon Dunes, caddies are idolized. 

Caddies have played an integral role in golf for more than 500 years, and the program at Bandon Dunes is among the best in the world. Where your average shack might contain 30, 50, or even 100 caddies, Bandon is teeming with 400 hungry sharks, ready to walk six or more miles a day with a bag strung over each shoulder. The loopers at Bandon are independent contractors—mercenaries who scour the sand dunes for errant shots, cash, dropped headcovers. And like good caddies everywhere, Bandon’s loopers are professional observers, making dozens of snap judgements about how best to take care of their players for the day. 

Bandon looper Jason Calamaro — affectionately known on property as “Squid.”

Bandon is an epicenter for the modern golf experience; it’s where every devout golfer makes pilgrimage. To call Bandon a resort is a slight. This isn’t your all-inclusive, strawberry daiquiri slurp-fest, where guests shuffle past you in search of the dinner buffet and tonight’s Dolly Parton impersonator. A more understated beauty exists here: “Golf as it was meant to be,” its well-earned slogan. 

Caddies at Bandon Dunes are tasked with knowing how every square foot of ground moves at the complex. While each course has its own pro shop, Head Professional, and maintenance crew, caddies move fluidly across them all, like ghosts, intimately studying the earth in its contours and wind directions; stockpiling data with little more than a naked eye, and a perked ear. The caddies are also studying you: indexing your sense of humor, supposing your priorities for the day, judging how you take direction. Don’t worry, it’s all to improve your experience.

Caddies are wizards at reading people, and it all starts with a handshake.

Say you and three friends brave the journey to Bandon for a week of golf. You plan on “touching them all,” and playing all of the six courses on property. If your group hires caddies, you’ll likely have the same loopers shouldering your bags for the duration of your stay. This not only gives the caddies some added schedule predictability, but allows a relationship to be forged between both parties—for you to feel comfortable with someone shepherding you around the place, and for the caddie to tailor their communication to you. 

Caddies are wizards at reading people, and it all starts with a handshake. “If their hands are on the softer side, I can guess they work an office job, or don’t really spend a ton of time outdoors. But if they’ve got strong hands or calluses, it signals to me that they could work in construction, or might want to be more independent on the course,” Bandon caddie, Jason Calamaro, shares. “It sounds weird, but it’s important for me to get as much information about people I’m caddying for as I can, even if it’s an assumption. It makes their experience better.”

Squid pictured on his daily commute.

Carrying bags is just the tip of the iceberg for a caddie’s role. A good caddie offers equal parts physical relief, golf course architecture lessons, stand-up comedy, strategic advice, emotional support, libations management, full-tilt psychotherapy, and hijinx stories. It’s up to them to gauge your personality and figure out which balance of those skills will enhance your playing experience.

The goal of any caddie should be that their players enjoy themselves: whether that means supplying the stories and laughs for an on-course party, or approaching each shot with the care and direction of a professional tournament round. It’s therefore the caddie’s responsibility to assess where their players fall on that spectrum, without directly asking—it’s got to feel intuitive. You look for little things to determine what type of caddie you’ll be today: is the player meticulously studying the scorecard and yardage book on the first tee, figuring out how to pick apart the golf course? Do they have nearly a case of beer stashed in their bag? Are they asking you questions—about yourself, your family, your work, the course?

In my time as a caddie, I prided myself on correctly assuming how a player’s first tee shot would end up, squarely based on my first impression of their bag. Mixed set of mud-caked irons, five woods, and all sloppily organized? Yeah, that’s going in the swimming pool off the right side of the first hole. But if the player’s sporting a trusty set of old Titleist muscle backs, the sweet spots tinted sepia from hours of banging balls at the range: I’m in for a straightforward day, quite literally. 

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A good caddie offers equal parts physical relief, golf course architecture lessons, stand-up comedy, strategic advice, emotional support, libations management, full-tilt psychotherapy, and hijinx stories.

Calamaro is one of the top caddies in Bandon’s shack, but out here he’s known simply as “Squid”. It’s common for caddies to have nicknames, pseudonyms, aliases, even. “Your nickname has to be earned,” Squid says; bestowed upon you by the tribe of 400, for one reason or another. Caddies who saunter in trying to nickname themselves aren’t exactly met with open arms—but that’s another story for another time. 

Curious, now being on the other side of the bag, I asked Squid how he’d sized me up: what were some impressions he’d made from our first few holes together? “I’m caddying for you, aren’t I,” he responded diplomatically. “I could’ve said no. Could’ve said I was busy today.”

Caddying at Bandon, an establishment that draws repeat—even yearly—visitors, allows caddies like Squid to form long-lasting relationships beyond a guest’s week on property. Despite his work being at the mercy of golfers, Squid’s schedule is often booked out months in advance; visitors from around the country requesting his services well ahead of their trips. So while Squid and other top caddies at Bandon aren’t jostling for loops in the caddie shack every morning, they’ve got to continually make good impressions, read handshakes the right way, manage existing client relationships, and on occasion, turn requests down when they don’t have room on the calendar. 

I know you’re in a tough spot, but how does that lie make you feel?

Caddying is a job that sticks with you. It fits to your bones, calluses your tendons. If you’ve spent a few years lugging bags around, toiling, and fighting trench foot in the caddie shack, you walk—or, perhaps limp—away with an irrefutable set of stripes that others in the industry will instantly recognize. The fairways at Bandon are home to 400 of these guns-for-hire. So take one with you when you make your pilgrimage: you’ll learn more about the courses than you ever would on your own. And you might learn something about yourself on the way.

View Comments (5)
  • An excellent essay. I’m curious how well the caddies get tipped by blue collar guys vs techies/lawyers/doctors. Also, I’d imagine they don’t get a lot of blue collar guys playing Bandon. I’ve never used a caddy myself, I play Munis.

  • Had the distinct pleasure of having squid caddie for me a couple of weeks ago at Bandon. He is as good as they get!

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