Jack Flaherty reunion would give the Cardinals rotation flexibility in 2027

The St. Louis Cardinals have sure liked their reunions in recent years, and while sometimes they felt a bit too convenient, Chaim Bloom going after Jack Flaherty on a "prove-it" deal would make a lot of sense.

Jeff Jones presented Flaherty as a potential target in his subscription newsletter, "Words About Birds", which is 100% worth your time if you have the ability to support his work. I'll let Jones present his argument in the mold of Steven Matz's signing back in November 2021, but I want to talk about how Flaherty fits a lot of what I've been hoping the Cardinals would consider this offseason.

Jack Flaherty can have a "Dustin May-like" impact on the Cardinals in 2027

Since being traded by the Cardinals at the 2023 trade deadline, it's been an up-and-down experience for the recently turned 31-year-old right-hander from California. In 2024, Flaherty posted a 3.17 ERA (13th-best in baseball) in 28 starts, covering 162 innings and producing 3.4 fWAR, tied for 17th among all qualified starters.

He repeated the frequency of starts and number of innings in 2025 to a worse ERA (4.64), though many of the advanced metrics were similar to his 2024 campaign. Flaherty only made 19 starts (and one relief appearance) in 2026, and posted a 4.48 ERA in the process. His strikeout stuff has declined the last two seasons, though it's still at a well-above-average 26 K%.

I don't imagine Flaherty is going to be commanding a multi-year deal this offseason, and if he did, the value should be very manageable. My guess is he'd be looking to rebuild his value, and given his familiarity with St. Louis and their proof of concept with Dustin May, a reunion could make a ton of sense.

Entering this offseason, the Cardinals have Kyle Leahy, Michael McGreevy, Quinn Mathews, Andre Pallante, and Matthew Liberatore returning as starting options, with Tekoah Roby, Cooper Hjerpe, and Richard Fitts all likely to challenge for spots in spring training. Gordon Graceffo and Brycen Mautz could join that conversation as well, and at some point in 2027, names like Tanner Franklin, Liam Doyle, Jurrangelo Cijntje, and Mason Molina should all factor into the conversation.

So, why add Flaherty to that group? I'm glad you asked.

1. Adding Flaherty to the Cardinals' rotation only adds more options to their mix. It's true, you can never have enough pitching, so adding a veteran arm to that mix wouldn't be a bad idea at all, especially one with the kind of swing-and-miss that Flaherty has.

2. Whether it is Flaherty or another starter, adding a free-agent arm makes it even easier to trade one of their young starters like Andre Pallante or Michael McGreevy. They are both good players, but it is unlikely that both will be in the rotation beyond 2028, so maximizing their value now makes a ton of sense with higher-upside replacements on their way.

3. If the Cardinals are contending in 2027 and experience a number of pitching injuries, Flaherty can help them push for the postseason all year long. If they fall out of contention, he could become a top trade chip like May was. And if the Cardinals are in contention but have young arms ready to debut like Franklin or Doyle, they can flip Flaherty to another contender to clear the way for their own young arm.

4. Flaherty is an arm that presents a level of upside that can both raise the play of the Cardinals' rotation and make him an attractive trade chip come July. His ability to miss bats is real, and if he can regain his feel for his slider and/or curveball in 2027, there's a good chance he looks more like the 3.17 ERA that he had in 2024 rather than his recent production.

Flaherty's fastball has dipped a bit in velocity lately, but it actually played much better in 2026 than it had in seasons past. There seems to be more in the tank for the former Cardinals' first-round pick that is waiting to be tapped into again.

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