Caddying Your Way To The Top
originally published in The Billfold
August 10, 2016
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Ever since a young errand boy named Andrew Dickson first carried golf clubs for the Scottish Duke of York in 1682, caddy programs have lent an air of democracy to a place defined by its exclusivity. From the window of the clubhouse, where golfers and guests mingle over coffees and cocktails, the caddie shack offers a visible, if partially obscured, path by which any hard-working outsider can step in, prove their worth, and move up in the world.
Following my freshman year of high school, I spent a summer caddying at a small country club in the northwest suburbs of Chicago, just a few miles west of the fictional Bushwood Country Club (the setting of the 1980 cult comedy film Caddyshack, whose tagline quips: “Some people just don’t belong”). Both of my parents grew up in the area, where it was common for a local golf course to serve as a kind of elevated public square, a place for a town’s pushers and movers to gather, eat, drink, and conspire.
This crowd paid handsomely for people to help them play golf: as an entry-level “A” caddy, my pay consisted mainly of tips, and I could earn anywhere from $50 to $250 a day, depending on the generosity of the caddymaster’s assignment. Frugal club members tipped the minimum appropriate amount of ten bucks, while a particularly chipper guest might feel compelled to share a fifty- or hundred-dollar bill.
Beyond the lucrative pay, the biggest boon for a caddy has always been the opportunity to meet someone important. The country club where I worked hosted weekly banquets and golf outings, bringing together small business owners, real estate developers, corporate executives, state politicians, wealthy retirees. In a town adjacent to my own, the mayor’s office was literally attached to the clubhouse, overlooking the opening fairway.
Many self-made titans of industry cite caddying as an important chapter in their formative years, even as the job exposed uglier sides of the society they sought to join. Former General Electric CEO Jack Welch claims that he witnessed “every aspect of human behavior” on the golf course, and his own caddying career met an abrupt end when a club member asked him to fetch a ball from the middle of a pond. Jack responded by tossing the man’s golf clubs into the water.
Like any service-oriented profession, the art of caddying is more psychological than physical. Anyone can carry a golf bag, polish a set of clubs, track a golf ball as it sails through the air, or sweep away the footprints in a sand trap, ensuring the earth appears unscathed. Caddies of the highest order learn how to read a golfer’s temperament, anticipate their behavioral quirks, and supply advice (when appropriate) that emphasizes their strengths and downplays weaknesses.
Proper caddying demands unwavering respect for the golfers, even when their behavior becomes morally dubious. Not every golf course mirrors the caricature of upper-crust snobbery portrayed in movies and TV shows. But even at the relatively modest and tolerant country clubs that surrounded my hometown, startling acts of ignorance could be an ordinary occurrence, and that presented unsettling realities to an idealistic teenager.
Over the summer, my fellow first-year caddies and I learned to listen and nod every time Dr. Z ranted about the town’s new housing developments and how they attracted the wrong kinds of people. We smiled politely when Mr. Bailey joked that Jose and Luis, two of our caddy counterparts, probably “play fought” with knives at home. When a hot-headed golfer hurled his club towards the trees after a bad shot, we obediently retrieved the thrown object and returned it to its owner.
The most enduring lessons from my time as a caddy came during these fleeting moments, when a golfer’s unfiltered thoughts revealed a clear, unassuming, and semi-public prejudice. I often found that the highest forms of business and politicking that surrounded me were not a matter of tireless grit or clear-headed logic, but rather an immensely emotional exchange between strong personalities. Success was not necessarily a matter of working hard, but working the right people in the right way. In the words of Roger Sterling, the free-wheeling patriarch from Mad Men who inherited an advertising agency, “Half the time … business comes down to ‘I don’t like that guy.’”
This rarefied world is fading, or potentially awaiting transformation. The country club where I worked has since shuttered its doors, as have hundreds of other clubs across the country. Young Americans aren’t playing golf at nearly the rate of previous generations, and every year, more courses are closing than new ones are opening. But if you live in a pocket of the country where the golf course maintains its relevance, caddying can still present a transformative opportunity.
Despite the declining popularity of the game, caddy scholarship programs are expanding, supported largely by donations from deep-pocketed golfers who remain enchanted by the story of scrappy young individuals working their way up through the rungs of society. The largest and most prestigious of these programs is the Evans Scholars Foundation, which provides full college tuition and housing stipends to scholarship recipients, and is on pace to enroll 1,000 new caddies by 2020, up from today’s annual classes of roughly 850.
Although winning scholars continue to be disproportionately white and male, there is a growing number of recipients from outside this narrow demographic: women and young people of African-American, Hispanic, Chinese, Korean, and Indian descent. Pictures of these cohorts capture the jarring nature of progress, diverse groups of people set against the backdrop of a place that has long been the symbolic distillation of white privilege.
The scene evokes both the possibilities and limitations of our striving culture. Ladders of success are, and probably always will be, stratified and unevenly structured around pre-existing social networks, like the country club. But at least in the near-term, there will be hundreds of bright young caddies, from a greater variety of backgrounds, embarking on their ownHoratio Alger-like journeys, offering a narrative to again lift our spirits and carry us forward.