Our recurring list of the twenty-five greatest Cardinals of the last twenty-five years will run daily leading up to Opening Day 2021. In case you missed it, here are the prior entries.

Honorable Mentions

25. Todd Stottlemyre

24. David Freese

23. Andy Benes

22. Lance Lynn

21. Paul DeJong

20. Tommy Pham

19. Darryl Kile

18. Ryan Ludwick

17. Kolten Wong

16. Carlos Martínez

15. Woody Williams

14. J.D. Drew

13. Brian Jordan

12. Edgar Renteria

11. Ray Lankford

10. Matt Morris

9. Matt Holliday

Bob Gibson is the greatest pitcher in St. Louis Cardinals, and the gap is frankly astonishing given how old and successful the Cardinals franchise has been. Because of Gibson’s ubiquity, he became the gold standard for Cardinals pitchers not only in terms of his incredible productivity, but in terms of his persona. There is nothing inherent about St. Louis that it specifically prefers pitchers with a little bit of an edge, guys who are allowed (and preferred) to be gentlemen 99% of the time but are competitive maniacs when on the mound; it is simply that St. Louis is where Bob Gibson played.

Chris Carpenter isn’t the greatest St. Louis Cardinals pitcher post-Bob Gibson (though he is probably #2), but he almost certainly conveys Bob Gibson more than any other. His 6’6″, 230-pound frame contributed more to his reputation than his relatively finesse pitching style–he didn’t hit a ton of batters and his strikeout rates were never exceptionally high. But he was never shy about yelling on the mound nor about staring daggers at his opponents. Rival fans hated Chris Carpenter, which may have contributed more to St. Louis’s adoration of him than anything else.

But despite Carpenter’s iconic status with the St. Louis Cardinals, he was just weeks shy of his 29th birthday when he debuted for the team. And this wasn’t because Carpenter was a late bloomer in terms of getting to the big leagues–he made his MLB debut two weeks after turning 22 and accumulated 135 starts with the Toronto Blue Jays. Over the last quarter-century, Carpenter actually holds the same rank–third–on a list of most starts for both the Blue Jays and Cardinals. But in Toronto, Chris Carpenter was extraordinarily ordinary. Some seasons were better than others, but on the whole, by Fielding-Independent Pitching, Carpenter was exactly league-average, and by ERA and xFIP, he was slightly worse than average. In 2002, Carpenter was ravaged by injuries and he would be unable to pitch until mid-2003 at best. So when the Cardinals signed Carpenter in December 2002, to a one-year deal with an option for 2004, some fans were confused. Most fans didn’t care.

It turned out that Carpenter’s injuries were more serious than many had hoped–despite an attempt at minor league rehab starts, he was eventually shut down for the 2003 season with the team hoping he could bounce back in 2004. By this point, he wasn’t even assured a spot in the team’s starting rotation. Had Carpenter become what fellow 2004 rotation addition Jeff Suppan became as a nearly-thirty reclamation project–a perfectly competent back-end starter–it would have been a victory. Instead, Carpenter became the team’s best starting pitcher in 2004. He had a career-low walk rate and a career-high strikeout rate, and he sailed to a 3.46 ERA with a 15-5 record. Unfortunately, Carpenter wasn’t able to avoid injuries altogether in 2004–a mid-September injury sidelined Carpenter for the entirety of the 2004 postseason. His Cardinals postseason legacy would have to wait.

In 2005, bouncing back once again from an injury, Carpenter was even better. He overcame the obvious constraint of the inventor of the modern bullpen being his manager to lead the National League in complete games, he went 21-5, and his 2.83 ERA put him in a prime position to win the 2005 Cy Young Award. Additionally, Carpenter won his first two postseason starts–Games One against the San Diego Padres and Houston Astros–and was spared a loss in his next start when Albert Pujols hit a Brad Lidge pitch to The Woodlands. In 2006, Carpenter took an ever-so-slight step back–he was once again an All-Star, but he had to settle for being a Cy Young finalist rather than a Cy Young winner. At 15-8 with a 3.09 ERA, Carpenter had once again solidified himself as the team’s best starter–while the team had traded for Mark Mulder after the 2004 season to give the team a solid ace, Carpenter had taken that role. And Carpenter once again excelled in the postseason–he won two games in the NLDS and pitched a gem in Game 3 of the World Series, fanning six Detroit Tigers in eight innings while allowing just three hits and zero walks.

By 2007, expectations for Chris Carpenter were that he would be a Cy Young candidate. But in his first start of the season, on Opening Day following a World Series victory, Carpenter suffered yet another injury. At first, it was thought to be relatively minor, but he aggravated the injury in rehab starts and in July, he had Tommy John Surgery. Carpenter wouldn’t start another game for the Cardinals until July 30, 2008. He made three solid starts before suffering another shoulder strain. He made one more start and then was shut down for the season.

Entering the 2009 season, Chris Carpenter was a complete wild card. Thanks to the emergence of Adam Wainwright, the Cardinals no longer needed Chris Carpenter to be “an ace”–they just needed a starting pitcher. This could easily be the difference between another long, long summer in St. Louis and a postseason berth. But Chris Carpenter not only returned as a regular in the Cardinals rotation, but arguably surpassed the performance of Adam Wainwright–at least the Cy Young voters seemed to think so. Things began inconspicuously for Carpenter–he made two starts before missing a month of action–but then, upon returning on May 20, he rolled. He didn’t miss another start for the remainder of the season, on his way to an NL-best 2.24 ERA. He and Wainwright finished second and third in NL Cy Young balloting, and the duo seemed to certainly be the best one-two punch in the NL, at least until the Philadelphia Phillies traded for Roy Halladay. More on him later.

2010 was a forgettable season by Carpenter’s standards, though a 3.22 ERA and an All-Star Game appearance are hard to knock. Perhaps most importantly, though, he stayed healthy–Carpenter led the NL in games started and threw 235 innings. At this point, Adam Wainwright had clearly passed Carpenter as the team’s best pitcher, but Carpenter was a more-than-worthy second banana. But a late February 2011 injury to Wainwright, one which forced the two-time Cy Young finalist to miss the upcoming season with Tommy John Surgery of his own, changed things. Once again, in his age-36 season, Chris Carpenter was going to have to be an ace.

2011 was an ordinary regular season for Carpenter on the surface. His 3.45 ERA was good, if not spectacular in the relatively dead offensive era. His 11-9 record looked unspectacular, but given his rough start to the season–through June 17, he had a 1-7 record and a 4.47 ERA–his recovery was admirable. By peripherals, he was nearly as good of a pitcher as he had been in 2009–his strikeout rate was the highest it had been since 2006 and his walk rate had been trimmed as well. But more than anything else, 2011 was a season of bulk–Carpenter led the National League for the only time in his career in innings pitched, with 237 1/3. Early in the season, when the bullpen struggled, sticking with Carpenter seemed to be the best option. Late in the season, when the bullpen became a strength of the team, Carpenter still went deep to allow the bullpen to save itself for the team’s other starters.

Over Carpenter’s final five starts of the 2011 regular season, Carpenter was spectacular–of his five runs allowed, four came in the same game (a game the Cardinals eventually won). And with the Cardinals tied in the Wild Card standings entering the final game of the season, the team leaned on Carpenter heavily in a two-hit complete game shutout against the Houston Astros–he struck out a season-high 11 Astros batters in the game. Although Carpenter was less effective in Game 2 of the NLDS, pitching on short rest, the Cardinals still squeaked out a victory over the Philadelphia Phillies, and four days later, in a winner-take-all game against former teammate Roy Halladay, Carpenter once again dealt a complete game shutout, in a game in which the Cardinals scored just one run. He was less dominant, striking out three, but it would become the most iconic start of his career, which is a tall order considering what would come three weeks later.

Chris Carpenter was only required for one game against the Milwaukee Brewers, which he won. He got the start in Game 1 against the Texas Rangers, where he allowed two runs in six innings and produced an iconic highlight, diving head-first into first base on defense to beat out Elvis Andrus. In Game 5, he once again allowed just two runs, but this time, the Cardinals were unable to come away with a victory. A weather postponement for Game 6 allowed the Cardinals to give Carpenter, albeit on short rest, a Game 7 start, and like clockwork, he went six innings and allowed two runs. But this time, it was enough, and the Cardinals won their second World Series with Chris Carpenter as the team’s unquestioned ace.

In mid-September 2011, Carpenter had signed a two-year extension with the Cardinals to stay on the team through 2013. But as it turned out, his Game 7 triumph would be his final victory at Busch Stadium. In Spring Training, shoulder and neck discomfort required Carpenter to have thoracic outlet surgery which sidelined him until September 21. As yet a final wrinkle to his career’s folklore, Carpenter had a rib removed in order to relieve stress while pitching. Although the Cardinals lost all three of Carpenter’s late-season starts, he pitched reasonably well in all three, going at least five innings and allowing no more than three runs. Carpenter earned a spot in the postseason rotation and managed 5 2/3 shutout innings in a Game 3 NLDS victory over the Washington Nationals, during which the always light-hitting Carpenter managed two hits, including a double. In his two NLCS starts against the San Francisco Giants, however, Carpenter only went four innings in eeach, allowing five runs (though only two earned) in each, and taking a loss in each.

Unfortunately, despite Chris Carpenter’s legendary status as a Cardinal, his career went out with a whimper. In February 2013, he once again began experiencing pain in his right shoulder, and although he tried to rehabilitate in the minors following a Disabled List stint, he was quickly shut down for the season, and in November, Carpenter’s inevitable retirement from baseball was made official.

At the time of his retirement, Chris Carpenter was the longest-tenured player in the St. Louis Cardinals dugout. Although Yadier Molina had debuted in 2004, Carpenter was the last true major contributor from the 105-win Cardinals on the team. And despite his late start on developing Cardinals lore of his own, Carpenter spent a decade in St. Louis and became a beloved ambassador and a worthy through line connecting the early-aughts sluggers of the former Busch Stadium with the new generation which brought the Cardinals five consecutive postseason appearances at the new Busch Stadium. And while he is on this list as a result of his production, he lives on in Cardinals lore as a result of his essence.