When Jim Benepe gets dressed for his job as a sales executive with Phoenix Fuel in Sheridan, Wyoming, he slips on a Rolex watch, a daily reminder of a remarkable feat from 20 years ago.

In the summer of 1988, Benepe was a 24-year-old mini-tour pro who received a sponsor’s exemption into his first PGA Tour event, the Beatrice Western Open at Butler National Golf Club outside Chicago. Incredibly, he edged Peter Jacobsen by a shot. The records of the early years of the PGA Tour are incomplete, but Benepe is the only player in the past 50 years to win in his first PGA Tour event.

Although the victory itself was the stuff of fairy tales, how he did it was far from heroic. Benepe wasn’t in contention until the last several holes, and he three-putted the 72nd hole. But Jacobsen doubled the same hole, giving the title to Benepe.

That lightning bolt of a win helped him become the Rookie of the Year, for which he received the watch that he still wears. Unfortunately, the win was not an early  indicator of a successful career. Over the next three years on tour, the injury-plagued Benepe only had two top-10 finishes, and by the mid ’90s, the Northwestern grad had returned home to Wyoming to sell real estate.

Several years later, Benepe made a comeback, finishing 29th on the 2001 Nationwide Tour money list. But an ankle sprain that left him struggling to walk derailed his second chance at golf. “I was almost 40 years old, injured and not really going anywhere,” he says. “I had a daughter beginning high school, my father was aging, and I wanted to do other things than chase a golf ball around 30–35 weeks a year.”

Benepe’s final golf hurrah was qualifying for the 2005 U.S. Open at Pinehurst, where he missed the cut. Today, the man who made one of the most auspicious debuts in golf history struggles to break 90—but only because he often plays left-handed when he tees it up with his wife or friends. He likes the challenge of relearning the game from the other side of the ball.

“A lot of the fun I still get from the game is playing lefty,” laughs Benepe. “I’d like to become a bogey golfer someday.”