Cleveland: Roy Oswalt a Mississippi Baseball Legend

Roy Oswalt
Photo courtesy of Camden Depot

Best pitcher in Mississippi high school baseball history? Great question, and I have no definitive answer. But I know of only one pitcher for whom a high school baseball team was created, and he became a three-time Major League All-Star. His name: Roy Oswalt.

Tiny Weir High School, which no longer exists, was known for its remarkable football program, which won six state championships. Indeed, Oswalt was a safety and wide receiver on the Weir state champs of 1994.

“We allowed seven yards total offense in the state championship game,” Oswalt, now 37, said. “I think that’s probably still a record.”

But Weir had never had a baseball team until Roy Oswalt came along, a skinny 10th grader with a rocket for an arm. He was throwing 90 mph when he was 15 years old and didn’t weigh more than 140 pounds.

So was the baseball program at Weir really created because of one skinny kid’s right arm?

“That’s the way the story goes,” Oswalt says, chuckling. “My dad pushed for it and helped get it in front of the school board. They passed it. My daddy (a logger) cleared some trees for the field and we had us a team.”

That first Weir team played 16 games. Oswalt pitched 14 of those.

“I can’t remember our record, but we made the playoffs,” Oswalt says. “We made the playoffs all three years. Never could win the state.”

Oswalt, who started school a year early, graduated at age 17 and at 5 feet, 11 inches and 150 pounds. Remarkably, a guy who would later win 163 Major League games, was not recruited by a major college and not drafted by a professional team out of high school.

He went to Holmes Community College on a half scholarship “probably mostly because of a friendship between my football coach at Weir (Joe Gant) and the coach at Holmes.”

At Holmes, he grew two inches and put on about 20 pounds of muscle his freshman year. His fastball went from around 90 to a 97-98 mph. That got everybody’s attention, including the Houston Astros who drafted him after his freshman year and Mississippi State who signed him to a letter of intent. The Astros, who had drafted him in the 23rd round, signed him before the draft for close to first-round money.

“I had always wanted to pitch for State, but it was just too much money to turn down,” Oswalt says. The Astros were pitching rich at the time and it took Oswalt four seasons to make the Major Leagues. Once there, Oswalt became one of the most accomplished pitchers in the sport, 14-3 as a rookie in 2001, three times an All-Star, two times a 20-game winner, five times a top five finisher for the Cy Young Award. He was known for his competitiveness and for being at his best in the biggest games. He was the MVP of the 2005 National League championship series.

Before all that he was the pitching star of the U.S. gold medal-winning baseball team in the 2000 Olympics. His numbers — 163-102 record, 3.36 career ERA before his retirement in 2013 — certainly should merit consideration for Cooperstown. He is a cinch for the Mississippi Sports Hall of Fame. He will become eligible in 2018.

Oswalt, father of three girls all under age 10, now makes his home in Starkville. Yes, he says, he misses the competition Major League baseball provided.

“I do miss being on the mound with the ball in my hand and having control of a game,” Oswalt says. “I’ll always miss that. But I don’t miss the travel, not at all. I like having my clothes all in one place.”

When he’s not hunting deer, turkeys, squirrels, etc., Oswalt works as a baseball players’ agent with his former agent, Robert Garber.

Says Oswalt, “Baseball’s still part of my life; it always will be.”

Rick Cleveland rcleveland@msfame.com is executive director of the Mississippi Sports Hall of Fame and Museum.