The Caddie Wore a Rolex

Several years ago, my friend (and self-made millionaire) Nate offered to pay me $6,000 a month to follow a story he believed would make a gripping book and movie. My job was to track the story’s progress, scribble notes and wait to see whether certain events panned out in a way that would make them worth writing about. At the time, I was between book contracts and struggling to finish a novel, and found his proposition too sweet to pass up.

Nate’s story was about Jerry Major, a 41-year old golfer who’d qualified for the U.S. Open 20 years earlier but, under the squeeze of family pressures, had given up his TOUR aspirations to teach lessons at a local muni course. Now, two decades later, Major had roped a sponsor and was training balls-out for Qualifying School and his second– and likely final– shot at playing on tour. As an afterthought, Nate admitted that he was the sponsor. And confessed that he’d be carrying Jerry’s bag. He’d even developed a title for the project: “The Caddie Wore A Rolex.”

It was a good tale: in addition to the Tin Cup drama of Jerry’s quest, each of these men possessed something the other needed. Jerry, blessed with astonishing natural talent, had struggled financially most of his life. He also lacked confidence. He could spank 350-yard drives and conjure magical recovery shots from off in the tulies, but he could also blow up on the easiest holes and sabotage his own chances of winning. Jerry engendered a childlike uncertainty and seemed somehow incomplete. In many ways, he yearned to be more like Nate.

Nate was a gregarious Midas– funny, loping, the kind of guy that waiters love, a former European-tour basketball player who still got juiced on sports. He enjoyed hanging with other athletes, and after retiring at age 42 and taking a year’s sabbatical, he craved a physical job where he could work outdoors. Nate also recognized that his own greatest skill was promoting other people’s talent. He’d decided that becoming a PGA TOUR caddie would be fun, and he believed Jerry’s ability was a fast cab to his destination.

I joined them as they scouted and played golf at various possible Q School locations to determine which best suited Jerry’s game, and as they competed in several local and Nike Tour events. From the first tee, I sloughed all pretense of journalistic neutrality and cheer-led for Jerry’s unlikely success. Then, when I got to know him better– witnessed his angry temper, watched him behave badly in public, and saw him abuse his caddie (who good-naturedly left Jerry to carry his own bag after such outbursts)– I began half hoping he’d fail.

But under the tutelage of sports psychologist Chuck Hogan, Jerry– not much of a philosopher– pivoted inward and began to examine his life. He quit drinking. He took on some lifelong demons in straight-up match play. Nate and Chuck weren’t just remaking Jerry into a better golfer. They were shaping him into a better man. How could I not root for a guy who was retooling his entire personality under the metaphorical guise of trying to play the best golf of his life? I became vulnerably entangled with my subject; emotion replaced analysis as my tuning fork. I stood behind Jerry without realizing that he wasn’t the only one being transformed.

Of course, our story was about the caddie, too. One of the most poignant moments in the project occurred at a Nike Tour event in Olympia, Washington. It was storming hard when I arrived at the golf course. Nate greeted me and we walked up to the clubhouse together to find out when play might resume. At the front door, he said he’d wait for me there, out in the rain; as a caddie, the millionaire wasn’t allowed inside. This amused Nate, who always knew who he was.

For three months I walked fairways and shared meals and traveled alongside the golfer and the millionaire. Jerry played erratically, outdriving young studs half his age and then throwing petite mal tantrums when he yipped a short putt or chunked an approach into the sand. In the first round of Q School in Llano, California– a place Nate joked was where they send people in the witness protection program– Notah Begay trounced the field and Jerry Major missed the cut by one stroke, in a playoff, thus ending what had finally become our mutual quest. It was not a failure of ability as much as of ambition. Golf only allows us to accomplish what we believe ourselves capable and deserving of.

Ultimately, I’d begun hoping that Jerry might actually sail through Q School and earn his PGA TOUR card. But just by allowing myself to feel for him despite his imperfections, I had moved on to my own next round. I’d swapped out judgment for sympathy– something the best writers always seem to manage, and a lesson I’d long needed to learn.

When it was over, Jerry wasn’t able to reclaim his teaching job so he launched a new career selling windows– an apt metaphor– at which he excels. Nate succeeded in a way nobody could have foretold but which we should have figured on anyway. Through contacts he made during our sojourn, he was offered a chance to carry David Ogrin’s bag on the PGA TOUR, which he tried out and decided wasn’t for him, after all. I used the money Nate had paid me to help with the down payment on my first house– something that had always seemed beyond my reach.

It’s taken me several years to see that our strange triumvirate’s time together was mostly about the vagaries of success. Quantifying victory in dollars or by golf scores, I learned, means overlooking a parallel universe in which the very best thing a man can accomplish is to be fully himself, improving upon that where possible and accepting his own– and other people’s– limitations with humor and grace, as Nate always did. I also learned that at times we all need someone to help us choose the right stick.

Nate, I finally came to understand, is a man who carries things– and not just golf clubs and tees, towels and energy bars. In Jerry and me, he saw some things that needed carrying, and for a while, he toted us, too.

One Response to “The Caddie Wore a Rolex”

  1. David Gould

    On a standard mid-week tour of the mighty APosition I came across this yarn of yours. Searched the brain for any recall of it, in pitches you may have sent me, or just phone conversation. Such a cool and prototypical guy-story. And very nicely told, amigo. Glad I glimpsed it. DG

Leave a Reply

You must be logged in to post a comment.