Most Little League World Series Players Dream of the Big Leagues. He Dreamed of Dentistry

When Robert Woolery played in the LLWS 66 years ago, his highest ambition was to become a dentist. This is his story.

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This story was originally published on Aug. 25, 2022. It was included in a year-end list of SI’s best stories of 2022.

In 1956, Sports Illustrated surveyed players at the Little League World Series. The question was, “What is the height of your ambition?” And the answer, for almost everyone, was, “I want to play baseball.” In other words: Exactly what one might expect.

But not for Robert Woolery of Colton, Calif. The 12-year-old pitcher knew just where his ambitions lay: He wanted to be a dentist. Well, sure, a ballplayer, too. But a dentist first.

“A dentist,” Woolery told SI. “My uncle is a dentist. He tells me that’s much better for a boy than to play baseball for money. So I told him O.K. But most of all I want to play baseball. If I am any good and if dentistry interferes with baseball, I’ll give up dentistry like [dentist turned pro golfer] Cary Middlecoff did. There’s a smart guy.”

Even with Woolery’s acknowledgement that, ideally, he’d still be a ballplayer, his answer stood out: It’s a rare 12-year-old who leads with the most practical version of his career plan when asked to describe his ambitions. It probably goes without saying that he was the only player at the 1956 Little League World Series to harbor dreams of dentistry (or, at least, the only one to admit as much on the record to SI). But he stood out in another way, too: He actually fulfilled his dream. A major league future did not await Ronald from Michigan, or Fred from New Jersey, or Tom from New Mexico. But Bob from California? He did it. He was a dentist for 50 years.

So: How’s it feel to be the one kid who got to grow up and live the (reasonable, well-considered) dream?

“You know, you say things when you’re 12, and they may not come to fruition,” Woolery says now, reached by phone at home this week in California. “But I really thought I could do something with my hands and my brain at the same time.”

And so he did.

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He realized, even back then, his answer was a bit unusual for a 12-year-old: He didn’t know many other kids with an interest in dentistry. But Woolery had his reasons. His father was a mechanic. His uncle Chuck, like he told SI in 1956, was a dentist. The two had a deal: When they visited one another, his father would handle his uncle’s car, and his uncle would take care of the family’s teeth. The arrangement led to a revelation for the young Woolery. He watched his father work on his uncle’s car on and off over the course of an entire week. He watched his uncle handle all the family teeth cleanings in one afternoon and then go fishing. It was clear for Woolery: Yes, he admired his father, but he knew which job he would rather have. So began a lifelong interest in dentistry.

Woolery never wavered. (Not even when a high school counselor said he didn’t have the aptitude to become a dentist.) And even after years of working toward the job—what he’d wanted since childhood—he found that it lived up to his expectations.

“You’d have a patient come in, and after so many years of experience, you could tell when they were in supreme pain,” Woolery says. “And when you could see all that pain go out of their eyes, it was probably one of the most rewarding things I think I’ve ever done, just to be able to help people like that.”

Woolery retired in 2018 after five decades of practicing in California. He still thinks of his years as a dentist fondly—and his years as a Little Leaguer, too.

The details of that 1956 World Series still resonate for Woolery. He remembers being so nervous ahead of the first game that he threw up before taking the mound. He remembers the feel of his brand-new glove—a special gift from his father—and how he realized after fielding just one grounder that he’d better switch back to the trusty old glove that got him there instead. The game went into extra innings, and in a time before youth pitch counts, Woolery pitched all eight frames. He still remembers the name of the boy who hit a home run off him in the top of the eighth, and of course, he remembers how it felt to watch his team come back to win it in the bottom.

Woolery pitched eight innings in his team’s first game in the 1956 Little League World Series at Memorial Field in Williamsport, Pa.

Courtesy of Little League Baseball and Softball

Woolery’s team lost its next game and was sent home. But the memories of that summer always remained precious. He returned to Williamsport in 2016 with his wife for the 60th anniversary of his World Series trip and even threw out a first pitch at a game.

“The whole experience was just mind-blowing for a 12-year-old kid,” Woolery says. “I just felt so proud to be able to do that—and to see all those kids now, to look at that audience, that beautiful stadium.”

He still watches some of the Little League World Series from afar each summer. The kids on the field now are living the same dream he and his teammates did so many years before. And Woolery, of course, is living proof: Some dreams do come true.

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