The St. Louis Cardinals are on the right track despite missing the postseason four straight years. The team is looking much better thanks to the rebuild they have initiated, and just because they're rebuilding doesn't mean that they can't make some upgrades to their roster for 2027.

The starting rotation is a place they could look to upgrade, and former Cardinal Dustin May could be an option for the 11-time World Series champions after the World Series reaches its conclusion. However, Will Leitch of MLB.com listed another former Cardinal that a reunion with would make sense, Jack Flaherty.

"Perhaps a reunion would make some sense for both parties. Flaherty is no longer the electric young phenom he was seven years ago, but he still has good stuff, with a 26% strikeout rate in 88 1/3 innings in 2026," Leitch wrote. "Flaherty didn’t pitch much this year because he went on the IL in July with right forearm flexor inflammation and didn’t return until the season’s final day. He just turned 31, which is relatively young, and only slightly older than May was when he signed his deal with St. Louis last year."

How Jack Flaherty Fits in St. Louis

May signed a one-year contract with an option last December to join the Cardinals. Perhaps a similar deal could be on the horizon for Flaherty.

The veteran right-hander began his career in St. Louis in 2017 and even received Cy Young votes after a dominant second half of the 2019 season. In 2021, injuries became a problem for the right-hander, so that is something the Cardinals are going to need to look out for.

The right-hander made 19 starts and one relief appearance for the Detroit Tigers in 2026, going 3-8 with a 4.48 ERA and striking out 103 batters in 88 1/3 innings pitched.

If he can stay healthy, he could be a perfect addition for the Cardinals based on where they are in their rebuild. He could be a trade candidate at the deadline if things go south, but he is also somebody who could benefit from the pitcher-friendly environment of Busch Stadium.

He helped the Los Angeles Dodgers win the World Series in 2024, so he does have a little extra postseason experience since leaving St. Louis. He also won the clinching Game 5 of the NLDS in 2019 for St. Louis.

Flaherty will likely command a similar deal to what May got last year.