Chris Carpenter
After Gibson won his second Cy Young Award in 1970, no Cardinal would win the award for the next 34 seasons. There were some close calls, which will be discussed later. However, nobody could snap the drought, which lasted into the new millennium. Enter Chris Carpenter.
Carpenter, 22 at the time, debuted in Toronto in 1997 and the results were uninspiring. Six years later, he was still an unremarkable pitcher, although he now lacked the leeway often extended to young players. Over his six seasons in Toronto, he made 135 starts, posting a 4.83 ERA. He lost 50 games and won just 49. The Blue Jays released him following the 2002 season. Just two months later, he was signed by the St. Louis Cardinals for $300,000.
Carpenter made his Cardinals debut 18 months later and broke out in 2004. He looked like a completely different pitcher. Carpenter showed vastly improved control and his strikeout rate increased significantly. By 2005, he was one of the National League's premier pitchers. He pitched excellently that season and was the ace of a 100-win Cardinals team. Carpenter, not previously known as a workhorse, led baseball with seven complete games that year en route to the Cy Young Award. Moving forward, Carpenter was a dominant pitcher. He was a Cy Young finalist again in both 2006 and 2010 when he absolutely should have won the award.
Perhaps the best moment of Carpenter's career came in 2011 when he guided the Cardinals to their 11th World Series title. Carpenter carried the team at times and turned in multiple iconic performances, including his NLDS Game 5 complete-game shutout in Philadelphia. By the time of his retirement after the 2012 season, Carpenter had won a Cy Young Award, two World Series titles, an ERA title, and had been selected to three All-Star Games. His dramatic transformation between 2002 and 2004 resurrected a dying career. Carpenter is a member of the Cardinals Hall of Fame and will always be remembered for his heroics during the postseason runs of the early 2000s.