He missed the 2011 season due to Tommy John surgery, but emerged as an ace, leading the National League multiple times in wins, innings pitched, and games started.

[5] His parents divorced when he was seven years old and his father moved to Florida, leaving only Wainwright's mother to raise him and his older brother Trey, now an attorney in Atlanta.

[6] The Atlanta Braves selected Wainwright 29th overall in the first round of the 2000 MLB draft, using a compensatory pick from the Arizona Diamondbacks for signing Russ Springer in the offseason.

He pitched for the Macon Braves in the South Atlantic League in 2001, where he broke the team record for strikeouts, previously held by Bruce Chen, with 184.

[7][8] In December of that year, the St. Louis Cardinals acquired Wainwright and pitchers Jason Marquis and Ray King in a trade that sent outfielder J. D. Drew and utility player Eli Marrero to the Braves.

[7][10] Wainwright made the Cardinals' Opening Day roster as a relief pitcher after having been a starter for his entire minor league career.

He saved two crucial games on September 27 and 30 as St. Louis held off the Houston Astros' late charge and won the NL Central Division championship.

Shortly after losing ace Chris Carpenter for the year due to elbow surgery, Wainwright emerged as the Cardinals' most reliable starter.

[18] On September 26, Wainwright pitched eight innings and struck out eleven for a 6–3, NL Central division-clinching victory against the Colorado Rockies at Coors Field for his 19th win.

He faced five batters, throwing 17 pitches for ten strikes and seven balls, and allowed no runs with just one hit—a double off the glove of fellow Cardinal All-Star Matt Holliday—one walk, and two strikeouts.

Three days later, the Cardinals announced that Wainwright would miss the entire 2011 season—and possibly the first three months of the next season—after finding that ulnar collateral ligament damage necessitated Tommy John surgery (TJS).

[30][31] Wainwright's contract featured options for 2012 and 2013 totaling $21 million with a provision that they would not automatically vest if he ended the 2011 season on the disabled list.

[48] Two days later, Wainwright, who was second in the league with 18 entering the game, defeated the Chicago Cubs in his final start of the season to tie Zimmerman for the lead in wins at 19.

[50] The Cardinals faced the Boston Red Sox in the World Series, and called upon Wainwright to start Game 1 against Jon Lester.

Wainwright struck out 10 in seven innings, becoming the first Cardinal to reach double digits in strikeouts in a World Series game since Gibson against the Detroit Tigers in 1968.

[61][62] However, he missed his June 16 against the Mets due to elbow tendinitis, but an MRI showed no structural damage to the Tommy John surgically repaired ligament.

[63] After leading the NL with a 1.79 ERA and 11 wins through July 6, Wainwright was selected to his third All-Star Game at Target Field in Minneapolis, Minnesota.

After working diligently to accelerate his recovery, the Cardinals announced on September 21 that he was cleared to resume baseball activities, two weeks prior to the conclusion of the regular season.

[82] Making his first appearance of the season since April, Wainwright pitched a scoreless inning of relief in the first game of a doubleheader against Pittsburgh on September 30, an 8–2 loss.

[88] In each of four consecutive plate appearances spanning April 27 to May 7, he became the first Cardinal pitcher since 1900 to garner an extra base hit while batting, per Elias Sports Bureau.

[90] Wainwright pitched a three-hit, complete-game shutout and 5−0 win against Miami on July 15, 2016; the first hit he allowed was a double to Adeiny Hechavarria in the sixth inning.

[95] Wainwright pitched six scoreless innings versus Los Angeles on June 1, while hitting a two-run home run facing Brandon McCarthy, for a 2−0 win.

[110] On April 26, Wainwright pitched a complete game against the Philadelphia Phillies in a 2–1 loss as Rhys Hoskins hit two solo home runs off him.

In an interview with Fox Sports Midwest, Wainwright remarked that the program combined his love of fantasy football with his passion for helping the less fortunate.

For a registration fee, all of which goes to charity, fans can assemble their own fantasy team and compete throughout the season against not only Wainwright but his current and former Cardinals teammates Allen Craig, David Freese, and Matt Holliday.

[143] Wainwright was the recipient of the 2020 Roberto Clemente Award due to his work with Big League Impact alongside his contributions in helping build Haiti's Ferrier Village Secondary School.

The majority of the work done was completed in 2015, after the opportunity presented to Wainwright due in part to the Achilles tendon injury he had suffered early in the season.

[150][151] On March 30, 2023, Wainwright surprised his teammates by performing the national anthem prior to the Cardinals' home opener against the Toronto Blue Jays.

"[152] Wainwright aspires to be a country music singer after his baseball career concludes; he held a concert in Springfield, Illinois, in January 2023 for approximately 500 fans.

[6] In a quirk of fate, he was in the midst of proposing to Curry in December 2003, when a telephone call interrupted him to inform him he'd been traded from the Braves to the Cardinals.