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

8. Chris Carpenter

7. Mark McGwire

6. Matt Carpenter

5. Scott Rolen

There are two players on this list of the twenty-five greatest players of the last twenty-five years who were traded as minor league prospects to the St. Louis Cardinals. For one of them, David Freese, the news was surely a dream come true–the opportunity to play in the organization of his youth and the promise that, if and when he made it to the big leagues, he would play in his hometown. For the other, Adam Wainwright, it was probably a nightmare.

Wainwright’s dream moment came in 2000, when the Atlanta Braves drafted him in the first round of the MLB Draft. Wainwright, a Georgia native and lifelong Braves fan, grew up idolizing Greg Maddux, Tom Glavine, and John Smoltz, and he would now have the opportunity to be teammates with them. He would eventually become teammates with Smoltz, but not in the way he expected. Wainwright ascended through the minor leagues with the Braves, and in 2003, in his age-21 season, he went 10-8 with a 3.37 ERA for the AA Greenville Braves. He was materializing as a worthy first-round pick with the potential to credibly succeed the trio who had dominated NL batters for the previous decade in Atlanta, but in the meantime, the Braves were preparing to compete in 2004 and they desperately needed another outfielder. And when J.D. Drew became available via trade, the Braves made the move, acquiring Drew and Eli Marrero for MLB pitchers Jason Marquis and Ray King, along with Wainwright, who was months away from being named MLB’s 32nd best prospect entering the 2004 season.

In the short term, the trade worked spectacularly for the Braves. J.D. Drew had an MVP-caliber season while Wainwright battled elbow issues and struggled in his early starts with AAA Memphis. But with Drew a free agent who went on to sign with the Los Angeles Dodgers, the Braves would be relegated to watching Adam Wainwright go forward and seeing the trade look worse and worse in hindsight. Wainwright bounced back in 2005, throwing 182 innings in AAA before receiving a September call-up. He struggled in his MLB cameo, but he did get in just under the wire of pitching at the old Busch Stadium, one of only two current (and this has been the case since 2013) Cardinals to have played at multiple Busch Stadiums in a Cardinals uniform.

For 2006, the bullpen-hungry Cardinals decided to let Adam Wainwright get acclimated to the big leagues gradually by letting him spend a year as a relief pitcher. Not only was Wainwright able to hold his own, but he became a valuable contributor to the eventual World Series champions. By both ERA and FIP, Wainwright was the team’s best relief pitcher throughout the season, and when Jason Isringhausen suffered a season-ending hip injury in September, Wainwright was elevated to the team’s closer. While the Cardinals stumbled into the playoffs, nearly squandering a seven-game division lead they held on September 20, they were eventually able to seal the division.

In each game the Cardinals won in the 2006 NLDS against the San Diego Padres, Wainwright finished the game. In each appearance, he struck out two batters. In only one game–game two–was the game close enough to make it a save situation, but regardless, Wainwright was able to close the door on each of these games with ease. In the next series against the New York Mets, Wainwright finished games 2 and 5, including a save in the latter, but it was his Game 7 performance which went into Cardinals lore. Inheriting a two-run lead, Wainwright allowed the first two batters to reach on singles before recording two outs, but following a walk of Paul LoDuca, Carlos Beltrán, one of the most famously clutch playoff performers in recent history, came to the plate with the bases loaded, the tying run on second base, and the pennant-winning run at first base. But Wainwright regrouped, striking out Beltrán looking on three pitches, with a tough curve down the heart of the plate sealing his fate. Wainwright would pitch three times in the World Series, including a Game 5 save which culminated with a strikeout of Brandon Inge to give the Cardinals their first World Series in twenty-four years.

Despite Wainwright’s coming out party as a closer, the team never seriously considered making him a closer in the long term–they knew what potential he had as a starter. Wainwright earned a spot in the 2007 rotation, and with Chris Carpenter’s season limited to a single start, Wainwright became the team’s de facto ace. In 2008, though he dealt with some injuries of his own, Wainwright was even better, with a 3.20 ERA. Once 2009 came around, Chris Carpenter was ready to once again make a meaningful contribution at the Major League level, and Wainwright elevated his game to keep pace. While Carpenter wasn’t quite ready for workhorse-level innings, Wainwright led the National League in starts, innings, batters faced, and wins. With a career-best 2.63 ERA, Wainwright led a crowded three-way field in first-place Cy Young votes, but he ended up finishing behind both Carpenter and eventual winner Tim Lincecum for the hardware.

In 2010, Wainwright was somehow even better. Roy Halladay’s move from the American League to the National League meant that Wainwright wasn’t a serious Cy Young candidate, but he was the rightful second place finisher thanks to a 2.42 ERA, a career-high 213 strikeouts, and his first twenty-win season. Chris Carpenter pitched respectably in 2010, but it was clear that Adam Wainwright had become the team’s best starting pitcher by the end of the campaign. But then in Spring Training the next season, the injury bug which had so thoroughly afflicted Chris Carpenter struck Wainwright, and in early March 2011, he was forced to undergo season-ending Tommy John surgery. Somewhat paradoxically, while Wainwright was a statistical nonfactor during the team’s improbable 2011 World Series run, the season may have been a net positive for how beloved he would become in St. Louis. He claimed in August (mind you, when the Cardinals were 10 1/2 games back of a playoff position) that he hoped the team would come back so that he could contribute to the team’s postseason run–while this may have been sarcasm regarding the team’s playoff odds, and it certainly wasn’t a realistic depiction of the timetable of returning from Tommy John surgery, the words were nevertheless exhilerating. And where Wainwright couldn’t contribute on the field, he did in the clubhouse, where he remained a mainstay as a team leader.

Wainwright returned in 2012, and on the surface, it was a mediocre year. Excepting his two-game cameo in 2005, his 3.94 ERA was the highest of his career. When manager Mike Matheny could select any Cardinals starter in their winner-take-all Wild Card Game against the Atlanta Braves, he opted for Kyle Lohse. And while Wainwright pitched very well in Game 1 of the NLDS against the Washington Nationals, striking out 10 in 5 2/3 innings, he was a disaster in their winner-take-all Game 5–the offense surged to save the game for the Cardinals, but Wainwright allowed three home runs and six total runs before being chased in the third. But peripherally, Wainwright’s walk and strikeout rates remained more or less intact, and his 3.10 FIP was actually the second-best mark of his career, trailing only his dominant 2010. There was reason for optimism, and in 2013, everything came back together–Wainwright shredded a full walk off of his walks-per-nine rate on his way to a 2.94 ERA and 2.55 FIP with an NL-leading 241 2/3 innings pitched and a second-place Cy Young finish. In the postseason, despite a somewhat dubious 2-3 record, Wainwright recorded four quality starts (and in his one non-quality start, he still only allowed three runs over five innings–hardly a disaster) and in his second winner-take-all NLDS start in as many years, this time against the Pittsburgh Pirates, Wainwright allowed just one run in a complete game victory.

Adam Wainwright was once again dominant in 2014–his 2.38 ERA was a career-best, he tied his career high with 20 wins, and while his FIP did go up, it trailed only 2013 and barely 2010 in terms of the finest marks of Wainwright’s distinguished career. For the fourth time in his career, Wainwright was a Cy Young finalist–while you could squint and find some cases for Wainwright among these, voters probably got each of their Cy Young choices correct. Despite his regular season success, come playoff time, there was intense media speculation that Wainwright was battling through injuries. The decision by Mike Matheny to start Game 5 of the NLCS against the San Francisco Giants was heavily scrutinized, but Wainwright gritted out seven innings while allowing just two runs, and Matheny would instead be criticized for bringing in Michael Wacha in relief in the ninth inning for the rest of time.

Over his first four starts in 2015, Wainwright looked to once again be a Cy Young-caliber pitcher–he sported a 1.44 ERA and 2.05 FIP. But then, a freak injury immediately ended the Adam Wainwright–Cy Young Candidate era: he suffered a torn left achilles while batting. He was initially believed to be out for the season, though he did return in late September and for the postseason to pitch in middle relief for the Cardinals, and he performed reasonably well. But while Adam Wainwright as relief star was refreshing and exciting in 2006, it felt incomplete in 2015.

2016 was the worst season of Adam Wainwright’s career–his 4.62 ERA and 3.93 FIP, while not terrible for a back-end starter, was hardly befitting his lofty status. He was decidedly worse in 2017, a season plagued with multiple DL stints and ineffectiveness when healthy–his 5.11 ERA and 4.29 FIP were both below league average. And while his 2018 metrics were marginally better, it felt even more like the end of his career was rapidly approaching–he made three April starts before being shut down for a month, he walked six in 2 1/3 innings in his return, and was then sidelined for an additional four months. When Wainwright signed an incentive-laden one-year deal for 2019, it felt like a goodwill gesture from the Cardinals, and perhaps a mere public relations stunt to keep Wainwright from ever playing for another team.

To say that Wainwright returned to form in 2019 would be an exaggeration–his ERA and FIP were each worse than any of his pre-2016 seasons. But for a pitcher who seemed absolutely cooked and incapable of remaining healthy for several seasons to pitch 171 2/3 innings with almost exactly league-average numbers was a victory. By this point, Jack Flaherty was the undisputed best starting pitcher on the Cardinals; the team didn’t need Wainwright to be a superstar, they merely needed innings. For good measure, Adam Wainwright even supplied a gem of a start in Game 3 of the NLDS against the Atlanta Braves, pitching 7 2/3 shutout innings while striking out eight batters. At this point, he had virtually no velocity–late-career Adam Wainwright is the one of the most notoriously soft-tossing pitchers in the sport. But he made it work. As he always has.

In 2020, Adam Wainwright easily led the Cardinals in innings pitched, with 65 2/3 (this would put him at around 177 1/3 on a 162 game pace), and his 3.15 ERA and 4.10 FIP, while still a far cry from his absolute peak, were superior marks to those of the presumed staff ace Flaherty. By FanGraphs Wins Above Replacement, Wainwright was the most valuable pitcher on the Cardinals in 2020, making him the only pitcher in franchise history to hold such an honor for seasons in three different decades. At this point, Wainwright is almost certainly the second-greatest pitcher in St. Louis Cardinals history, and while he will probably not make significant noise when it comes time for Hall of Fame voting (assuming he ever retires), he will rightly be regarded as one of the great Cardinals lifers. And in the end, he seems pretty happy he got traded to the Cardinals.

3 thoughts on “The twenty-five greatest Cardinals of the last twenty-five years: #4–Adam Wainwright

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