Postseason Context and Roster Strategy
The St. Louis Cardinals are currently navigating an offseason focused on roster construction despite missing the postseason for four consecutive years. According to reporting, the organization believes it is on the right track following a rebuild initiated in recent seasons.
Reports indicate that the team is looking to make upgrades to its roster for the 2027 season. This interest extends beyond new free agents, with former players emerging as potential targets for reunion deals.
Jack Flaherty Emerges as Reunion Candidate
Will Leitch has written that a reunion between the Cardinals and pitcher Jack Flaherty might make sense for both parties. Flaherty, who began his career in St. Louis in 2017, received Cy Young votes after a dominant second half of the 2019 season.
Flaherty won the clinching Game 5 of the NLDS in 2019 for St. Louis before later helping the Los Angeles Dodgers win the World Series in 2024.
In 2026, Flaherty made 19 starts and one relief appearance for the Detroit Tigers. He finished the season with a 3-8 record and a 4.48 earned run average, striking out 103 batters in 88 1/3 innings pitched.
Leitch noted that Flaherty posted a 26% strikeout rate during his 88 1/3 innings in 2026. However, the pitcher's workload was limited due to health issues. He went on the injured list in July 2026 with right forearm flexor inflammation and did not return until the season's final day.
Flaherty turned 31 this offseason. Leitch suggested that a similar deal to one offered last December could be on the horizon for the pitcher, noting that he is only slightly older than Dustin May was when he signed his deal with St. Louis last year.
Injury History and Team Considerations
While Flaherty remains a viable target, his medical history presents factors for the Cardinals to weigh. Injuries became a problem for Flaherty in 2021, a period that the organization needs to consider if he returns to St. Louis.
Dustin May Also Linked to Cardinals
Alongside Flaherty, right-hander Dustin May is being viewed as another potential reunion candidate for the Cardinals. May could be an option for the 11-time World Series champions after the 2026 World Series concludes.
May was active during the postseason, throwing a pitch against the Tampa Bay Rays during the fifth inning in Game 2 of the 2026 World Series at American Family Field on Oct. 24, 2026.