Playing with a caddie

Playing with a professional caddie adds a layer of depth and delight to any round of golf. It’s more than someone carrying your bag—it’s a partnership shaped by trust, humor, and an almost uncanny understanding of the game. Every time I’ve had a caddie beside me, the round feels elevated, more connected to the roots of golf itself. They don’t just guide you to the right target; they guide you to the right miss—and, just as importantly, the smartest way to recover.

One of my favorite rituals is what I think of as the “committee meeting.” Four people gathered around a ball, pointing into the wind, weighing options. It looks like debate, but it’s really collaboration. By the time you step in, doubt has been replaced by commitment. The caddie isn’t dictating—he’s helping you see the hole the way it was meant to be played.

And when things inevitably go sideways, there’s no judgment. You might find yourself on a slope in thick rough, wondering how it unraveled so quickly. The caddie simply studies the lie and says, “Let’s just get it back down there.” No lecture, no frustration—just a calm reset and a path forward.

What makes caddies unforgettable, though, isn’t only their insight but their wit. A wry, “Where has that club been?” after a great shot, or a quiet golf clap near the clubhouse. They balance humor and honesty perfectly, easing tension while keeping you grounded.

I still remember Neil, my caddie at Royal Birkdale, whose dry English humor and spot-on advice made that round unforgettable. “Nothing else will do here, George, except pure rage,” he said at one point. Later came, “Get your hands up,” and, with a grin, “Stop thinking.” Simple words, but together they became the best playing lesson I’ve ever had.