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

By no measure was Woody Williams the best St. Louis Cardinals pitcher of the last twenty-five years. But he was probably the most St. Louis Cardinals pitcher of the last twenty-five years.

The Cardinals acquired Woody Williams just a few weeks shy of his becoming eligible to be United States president. Most of the players on this list concluded their careers in St. Louis before Gregory Scott “Woody” Williams began his. And it’s not as though Williams was a John Lackey-esque rental, where his time spent with the Cardinals was going to be inevitably finite but proof of concept existed that he could be a great Major League starting pitcher. Despite the Cardinals only ranking third in terms of teams where Woody Williams pitched the most innings, it was the team where Woody Williams accumulated the most Wins Above Replacement, and easily the team with which he achieved his highest peaks.

A Houstonian through and through, having been born, raised, and attended both community college and university (he attended Houston in their old Southwest Conference days) in the area, Williams was nearly 22 years old when he was drafted in the 28th round of the 1988 Amateur Draft (ironically, he was later traded for the other player drafted in that round who had a long MLB career, Joey Hamilton). Expectations were low, but at 26, he reached the big leagues with the organization that drafted him, the Toronto Blue Jays, where he pitched in 30 games. He was a decent, mid-to-low tier relief pitcher for the defending World Series champions, who later went on to repeat as champions that October, though he appeared in neither the ALCS nor the World Series. Over the next two seasons, Williams was a decent middle reliever for a Blue Jays team in decline–perfectly adequate, but not exactly a player that fans were clamoring for to get a chance to start. In 1996, however, he was promoted to the starting rotation, where he pitched three more seasons for Toronto. His ERAs sat in the mid-fours, moderately above average for the era, and in his latter two seasons, he gravitated around the 200 inning mark. He was, through age 32, the definition of “fine”.

The aforementioned swap with Joey Hamilton sent Williams to the San Diego Padres. After a middling 1999, Williams had what was to that point the best season of his career in 2000, when he went 10-8 with a 3.75 ERA. Sure, the Padres were a pretty lousy team, but he was certainly the team’s best starting pitcher that season. But in 2001, he got off to a rough start, with a 4.97 ERA in 23 starts. The Padres were a middling team, but the Cardinals were seeking a starting pitcher. And two days after the formal trade deadline, the Cardinals made an astonishing waiver-wire trade, sending Ray Lankford to San Diego.

2001 Ray Lankford was post-prime, though still a rather good hitter, albeit one without an obvious spot in the everyday lineup due to the increasingly common outfield of Albert Pujols, Jim Edmonds, and J.D. Drew. But more importantly, Lankford had been the best Cardinal of the last decade, perpetually underrated and overlooked outside of St. Louis (where he was still fairly underrated). And Woody Williams was just a guy.

Emphasis on was just a guy.

Woody Williams finished out the 2001 season looking like a legitimate big-league ace, with a 7-1 record and 2.28 ERA in eleven starts. He did this despite nearly identical walk and strikeout rates as in San Diego, but with shredding his home runs allowed rate. Was this luck? A little, but it wasn’t entirely–his transformation fit squarely within the Dave Duncan pitching template. Woody Williams was never a strikeout pitcher, and this wasn’t going to change in St. Louis, but he always had decent control, it was generally improving before he came to the Cardinals, and he was able to harness this into greatness. Maybe not sustainably 2.28 ERA greatness, but…let’s just say “very good-ness”.

In 2002, the final season of Woody Williams’s contract that the Cardinals had inherited, he dealt with injuries, but when he did pitch, he against all odds managed to more or less carry over his 2001 success. His ERA ticked up a little bit from his 2001 run with the Cardinals, but a 2.53 ERA in 103 1/3 innings at near the height of the steroid era’s home run craziness was extremely acceptable. His strikeout rate went up and his walk rate went down, too, so while 2.53 was still probably a bridge too far, it wasn’t as crazy to see.

In 2003, Woody Williams, who began the season at 36 years old, set a career-high in wins with 18, innings with 220 2/3, and he earned his lone career All-Star Game appearance. Despite no major changes to his peripheral statistics, Williams did suffer an ERA jump, to 3.87, but in this era, it still made him a definitively above-average starting pitcher. But the warning signs of decline were there–prior to the All-Star Break, Williams had a 3.01 ERA and 3.37 FIP, while after it, those numbers were 5.23 and 4.28. Williams did bounce back in 2004 from his second-half of 2003 lull, but with a 4.18 ERA and 4.10 FIP, he was finally starting to pitch like the tremendously average pitcher the Cardinals had expected him to be. By the 2004 season, Williams was now teammates with Ray Lankford, the player whose St. Louis exodus brought Williams to the Cardinals in the first place, as if re-signed as a means of dunking on the Padres for what turned into an unqualified win for the Cardinals.

Woody Williams was integral to the 2004 postseason run for the Cardinals–he was, despite his declining numbers, the team’s choice to start its first playoff game, which the Cardinals won after he allowed just two runs in six innings against the Los Angeles Dodgers. He then started in Game 1 of the NLCS, where he pitched less well but still got the victory, and Game 5, where the Cardinals lost on a ninth-inning walkoff to the Houston Astros but his seven innings of one-hit shutout ball could hardly be blamed. And then, he started the first World Series game for the Cardinals in 2004. As was the case for almost every Cardinals player in that World Series, the Boston Red Sox absolutely rocked him, but he did start it, so he has that going for him.

At this point, Woody Williams was 38 years old and, against all odds, still a moderately coveted free agent. He went back to San Diego on a two-year deal, and while he struggled in 2005, and while his run prevention recovered in 2006 to the tune of a 12-5 record and 3.65 ERA, his already moderate strikeout totals were plummeting even further. But still, the Padres won the NL West twice in his two seasons back in San Diego, and Williams was rewarded with being the losing pitcher in both elimination games. And both came against the Cardinals.

Williams signed a one-year deal for the 2007 season with his hometown Houston Astros, but now into his 40s, he was clearly a shell of his former self and he retired after the season. In 2013, he made it to the Hall of Fame ballot, and unsurprisingly received zero votes, but the fact that he even so much as made a Hall of Fame ballot, particularly given where he was at thirty, is a resounding success. And he made over $50 million in his career, so he certainly succeeded in navigating the Major League Baseball financial labyrinth. For that, and for his ability to find his best self as a Major League pitcher in his mid-thirties, Woody Williams deserves a ton of credit.