In a practice round during her rookie season on the LPGA Tour, she wound up behind someone Pepper would describe as an aging veteran who had no business being out there. Pepper turned to her sister, who caddied for her that summer, and told her, "Don't ever let me get to that point."
Two years after her first shoulder surgery, when those blue eyes didn't blaze with quite as much intensity and Pepper began to realize there was more to life than chasing around a little white golf ball, she announced her retirement at the 2004 U.S. Women's Open when she was 38.
Her retirement Sunday after eight years with NBC Sports was not much different.
"I would have to say this is similar to when Barry Sanders retired because she's going out on top of her game," said Tommy Roy, NBC's executive producer of golf who gave Pepper a chance, coached and critiqued her, and was sorry to see her go. "Her work this year on the FedEx Cup and the Ryder Cup was impeccable. You could take her work and make a 'how-to' tape for future broadcasters."
Her last day at work was Sunday at the Father-Son Challenge in Orlando, Fla., the end of a ride that Pepper, 47, could not have imagined.
It was former NBC staffer John Goldstein who persuaded Roy to give her a shot at the '04 Women's Open, and Pepper took it from there. She started work in 2005 during the Florida swing on the PGA Tour, and then got her big break
"You can't dream up an assignment like that," Pepper said. "My very first Open and I walk in the winner."
Just like her retirement from playing, however, Pepper caught herself pulled in another direction.
She was tired of the travel, for one thing, and she found her passion shifting to junior golf. The PGA of America called on her again, and this time, Pepper listened. She decided at the Ryder Cup to leave her role as the most prominent female golf analyst and join the PGA of America's board of directors, where she can work on developing junior golf programs.
Roy was effusive with praise.
"The great thing about Dottie is not many players could come over from the LPGA and analyze in a critical way how the PGA Tour players and still be respected by those players," he said. "She garnered so much respect from the players. She came over and fit right in."
That's all Pepper really wanted.
Roy said he would like to have another LPGA Tour player work the U.S. Women's Open next summer on Long Island, though it is not imperative for the NBC team to find another woman to fill Pepper's role. It was never about gender, and Pepper never saw it that way.
"It's been the greatest thing because I was treated as a reporter and an analyst, not because I was a woman," she said. "I was expected to toe the line. No matter how bad the weather was, how tough the walk was, I was to do everything the guys did. And that's how I wanted it."
She was never lacking in intensity and honesty, sometimes to a fault. She once was criticized for shouting, "Yes!" when her opponent missed a putt in the Solheim Cup. Roy laughed when recalling her early years with NBC. "Everyone on the NBC golf team was scared to death of her from when she was a player," he said.
That intensity, however, led to her lowest moment in broadcasting.
Pepper was working the Solheim Cup for Golf Channel in 2007 when the Americans kept missing one pivotal putt after another. They had gone to a commercial break, but someone forgot to hit the switch. Thinking they were off the air, Pepper said, "Choking, freakin' dogs!"
Only they weren't off the air, and her commentary got back to the Americans. Pepper didn't remember saying it and she didn't even find out about it until six hours later, when the telecast was over and a producer closed the door behind him and said, "We've got a problem."
"An enormously sick feeling," Pepper said. "The thing that still stings about that is that there were people at Golf Channel who had already packed my bags. They had issued my resignation. And (senior programming director) Don McGuire said, 'No, that won't be the case. That was our fault.' I'll always be appreciative of him for that."
Her sin wasn't being honest, rather it was being a cheerleader.
"That's what hurt the most," she said. "I was bleeding with them, and as a broadcaster, you can't do that. You call your sport."
Pepper wasn't sure she would recover from that, and there are still a few American players who won't speak to her. Once a shoo-in as a Solheim Cup captain, Pepper quickly became an afterthought except in the booth. That changed this year when Meg Mallon chose Pepper as one of her assistant captains for the 2013 matches in Colorado.
Will she be a captain someday?
"Only if I'm wanted," she said. "People have to want you to be a captain."
But she says her decision to leave broadcasting was in no way related to her future in the Solheim Cup.
It was simply time to move on to something else, which in this case is developing young American players at an early age. She has created a mascot called "Bogey," a big range ball who is tired of his dead-end job and wants to be a player. Pepper is bringing "Bogey" to the PGA show next month. She describes him as "a bridge so that golf isn't so scary to kids."
Pepper has no idea how long her stint with the PGA of America will last, but odds are she'll get out when she's ready and not a moment too late.