Jack Flaherty and the Tigers have kept in touch but a reunion seems unlikely

The former Tigers right-hander discussed the topic on the Foul Territory podcast, but a fit for the right-hander remains unlikely.

The relationship didn’t last long enough to get attached, but Detroit Tigers fans had some good times with right-hander Jack Flaherty in 2024. Of course, it didn’t hurt that Flaherty had perhaps the best four month stretch of his career under the watchful eyes of Tigers’ pitching coach Chris Fetter and his staff. Still, Flaherty is a likeable, thoughtful individual not afraid to speak beyond cliches. Performance is key, but his personality didn’t hurt in making him a popular player during his short time in Detroit.

Clearly Flaherty’s market hasn’t developed as he would’ve hoped in free agency this offseason. After firing 162 innings in 2024 with a 3.17 ERA and a 3.48 FIP, one might expect that nine figure offers would be on the table for the 29-year-old. That seemingly hasn’t been the case. He struggled through some concerning velocity dips down the stretch and in the postseason with the Dodgers , and that, coupled with a history of shoulder trouble, has presumably scared teams away from offering the big long-term deal. So it’s natural that thoughts have returned to the possibility of a short-term reunion with the Tigers.

Flaherty has had the same thought, as he discussed recently on the Foul Territory podcast. He spoke highly of his time in Detroit, saying that he loved it there and that “I’ve wanted to stay in Detroit.”

He went further, mentioning that he and his representation have had some conversations with the Tigers’ front office this offseason. The problem for the Tigers is that they’re still involved in the game of chicken with Alex Bregman and Scott Boras. Without knowing how that’s going to play out, and seemingly still holding that interest in the one player available that really fits a major need, it’s difficult to pivot to other options. On Flaherty’s part, he’s still hoping a sizable multi-year deal comes his way. The Dodgers are out of the picture, but there are plenty of teams like the Blue Jays, Cubs, and Red Sox, among others, who seem fairly serious about contending and still need real help in their rotation.

The Tigers’ success in helping Flaherty unlock a new level of performance does make a decent argument for a reunion, assuming he becomes more amenable to a shorter deal than the five year, $100M pact that seemed like his expectation this offseason. That may lend credence to the idea that they can get more out of him that other suitors might. At very least they have a lot more information on which to make a good evaluation of his health and likely future performance than anyone else out there.

The main adjustment in 2024 came when the Tigers coaching staff convinced him to ditch his cutter, feeling that throwing it was impacting his fastball release. They also helped him improve his mechanics, which helped prevent any significant injury other than a short stint with back spasms, allowing Flaherty to avoid any shoulder trouble and produce his highest innings total since 2019.

We can at least still dream of an offseason in which they sign Bregman, and then manage to land Flaherty on say, a two-year deal with an opt-out after year one. A rotation of Tarik Skubal, Jack Flaherty, Reese Olson, Jackson Jobe, and Alex Cobb, with plenty of reinforcements behind them, sounds really good. The Tigers clearly have the payroll room to sign Bregman, or they wouldn’t be involved in the first place. But they’re also extremely unlikely to stomach two long-term deals.

In particular, the Tigers just aren’t in any position to offer a nine figure deal to any starting pitcher right now. My best guess is that $150 million is about the absolute max they’re willing to stomach for a year’s payroll. At that level they could theoretically still turn a profit even if they did miss out on the postseason. Beyond 2025, their 2026 commitments currently remain around $80 million per year even with projected arbitration increases. It also feels as though a Skubal extension is pretty much off the table at this point.

Cobb, Kenta Maeda, and Gleyber Torres will all be off the books next offseason, but there’s still probably no way they’re going to commit to another pricey deal longer than one-or-two years if it isn’t Bregman, particularly for a starting pitcher. Under those self-imposed conditions, they can’t miss badly on a big deal, and missing is always a bigger danger with pitchers.

With the Tigers two years away from their next big wave of prospects arriving, there’s still an obvious window, or gap, if you prefer, in which they really should be trying to take advantage of Skubal and a coaching staff that feels well ahead of the curve of the moment. Doing so without overcommitting to long-term payroll obligations and limiting their options down the road remains the trick.

For now, the impasse in Bregman talks remains the block in the way of any alternate plans. Hopefully that doesn’t take too much longer to resolve, but either way, just keep Jack Flaherty in the back of your mind. If he ends up forced to take a short-term deal to try and prove 2024 was no fluke, the Tigers still remain a pretty good destination for him. Both parties would presumably be happy to reunite if the business side happens to work out that way.