Wainwright is a former Glynn Academy standout who went on to become a household name in Major League Baseball as a star pitcher for the St. Louis Cardinals from 2005 through 2023. 

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Wainwright was a pitcher and outfielder while playing under coach Chuck Fehr at Glynn. He batted over .400 three straight seasons including .515 as a senior. With a fastball clocked over 90 mph, he attracted the attention of professional scouts especially as a senior when he was named the Gatorade Georgia Player of the Year in 2000. 

He also played football for the Red Terrors and was a standout receiver and kicker, earning all-region honors at both positions.  

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Wainwright had baseball scholarship offers from both Georgia Tech and Georgia among others, but was chosen with the 29th overall pick in the first round of the 2000 MLB draft by the Atlanta Braves, his favorite team growing up. Despite Baseball America naming him the Braves top prospect in 2003, he was traded to the Cardinals after that season in a blockbuster, multi-player deal that sent him to St. Louis where he became a fan-favorite and one of baseball’s top pitchers during his long run with the franchise.

He made his major-league debut late in the 2005 season before making the Opening Day roster the next spring as a relief pitcher for the Cardinals despite always being a starter in the minor leagues. Early in the 2006 season, he hit a home run on the first pitch he saw in his first at-bat in the majors to become only the 22nd player in history to accomplish that feat. 

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That season, he ultimately became the St. Louis closer and saved the final game of the National League Division Series, then famously struck out New York Mets’ star Carlos Beltran in the NL Championship Series to send the Cardinals to the World Series, where he also struck out Detroit Tigers’ third baseman Brandon Inge to lift St. Louis to its 10th world championship. 

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Wainwright went back to being a starting pitcher the next season and would establish himself as the Cards’ ace for the next several seasons. He won 14 games his first season as a starter - the most in franchise history for a first-year starter. Among his best seasons was 2009 when he recorded an NL-best 19 wins while posting a 19-8 record. He won the Players Choice Award as the NL Most Outstanding Pitcher and was one of the top contenders for the NL Cy Young Award. 

Wainwright won 20 games the next season and was the runner-up in the NL Cy Young voting that year.He missed the 2011 campaign while recovering from Tommy John Surgery but watched as the Cardinals won the World Series again. 

Two years removed from the surgery, he was as good as ever in 2013 when he led the National League in wins while helping St. Louis to another World Series where the Cards fell to Boston in six games. He again was second in the Cy Young voting. He won 20 games a second time in 2014 and again finished third in the Cy Young race. 

For his career, Wainwright, also known as Waino and Uncle Charlie for his amazing curveball, won 200 games and recorded 2,202 strikeouts. He is one of only 122 pitchers in baseball history to reach the 200- victory milestone. He is third all-time in wins for the Cardinals behind only legend Bob Gibson and Jessie Haines. Wainwright’s strikeout total placed him among only 66 pitchers to notch 2,200 strikeouts in a career. 

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Also noteworthy, he was a three-time All-Star, two-time Gold Glove winner and also a Silver Slugger Award recipient. Wainwright and his longtime teammate and friend, catcher Yadi Molina, also are the most successful battery of all-time with the most wins and starts together. 

Wainwright was chosen as the 2020 recipient of the Roberto Clemente award which is presented  annually to the MLB player who “best exemplifies the game of baseball, sportsmanship and community involvement and the individual’s contributions to his team.” 

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He participated in the 2023 World Baseball Classic with Team USA before completing his career in the 2023 season which he said would be his last before it started. He was inducted into the Missouri Sports Hall of Fame shortly after his final big-league season.

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 In retirement, Wainwright is living locally with his wife Jenny and five children. While pursuing a career in country music, he has worked as a studio analyst for the MLB Network and is also calling games as a color commentator for Fox Sports.