After a tumultuous introduction to golf, Thomas Trinchitella has carved out an unlikely career as Pinehurst Resort’s most trusted caddie
Few people would develop into avid swimmers if their introductory lessons included being thrown into the deep end of a pool and being told to figure it out. But that was how Thomas Trinchitella learned to play golf.
In his early 20s, Trinchitella and a buddy went out to Ole Bluff, a par-3 course in Hope Mill, N.C., “just for kicks.” Equipped with an antiquated set of clubs that belonged to his friend’s grandfather—and having never hit a golf ball—they set out to see what all the fuss was about. “Neither one of us knew what the hell we were doing,” he recalls with a chuckle.
As you might expect, it didn’t go well.
“Oh, it was horrible,” Trinchitella says. “I couldn’t hit a driver 100 yards.”
Every weekend, Trinchitella was back at Ole Bluff, shouldering a bag of five uninspiring rental clubs “trying to make it happen.” In the beginning, he was entirely self-taught. “That’s what drove me,” he says of the motivation to figure out how to do it. “Golf really grabbed me.”
In many ways, such a trial by fire conditioned Trinchitella for his eventual career as a caddie—a professional chapter that began during the early 2000s at Pinehurst and has never wavered. Today, the soon-tobe 52-year-old is one of the longest-tenured caddies at the resort, but when he first started looping at America’s cradle of golf, it was only a part-time job. He’d responded to an ad in the local paper promoting opportunities as a caddie, but once he was laid off from work in the furniture and cabinet industries, he looked to pick up more bags. “I fell into it full time waiting for the next best thing,” Trinchitella says. “Who would’ve guessed that caddying would be it?”
Asked what it’s like to play a round on the No. 2 course, the Donald Ross-designed gem where Trinchitella spends most of his time—at least when donning the customary white caddie jumpsuit—he answers with more ambiguity than clarity, despite more than two decades of experience there.
“It’s indescribable,” he says. “You cam’t play No. 2 and then describe [to someone who hasn’t played the course] the good and the bad that happened to you. They wouldn’t understand it. You hit the best shot of your life and you’re 20 feet off the green even though it landed five feet short of the flagstick. That sort of thing happens on every shot.”
Over the years—in part for his ability to navigate the challenging course that is set to host its fourth U.S. Open, but mostly for his interpersonal skills—Trinchitella has become the man in Pinehurst’s caddie corps that both Tom Pashley and Don Padgett II, the resort’s current and former presidents, respectively, have trusted to shoulder the bag for VIP guests. That list includes major champions such as Tiger Woods, Rory McIlroy, and Annika Sorenstam, as well as President George H.W. Bush. “Anytime we ever had a special person, for whatever reason, who needed a caddie,” says Padgett, “I always said, ‘I have just the guy.’”
Trinchitella also served as the regular caddie for Pinehurst’s owner, Bob Dedman Jr., for more than a decade. During one of those rounds, on the No. 4 course, Trinchitella retrieved a wayward shot from under a holly tree on the 16th hole. To Dedman’s surprise, the five-foot-six caddie was able to walk beneath the bottom-most branches without ducking. That prompted the owner to dedicate the tree with a sign that reads, “In honor of Thomas Trinchitella: a faithful caddie—short in stature and long in wisdom.
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