Tigers should get ahead of extension talks with Jack Flaherty to avoid contract hassle

Jack Flaherty returning to the Tigers in free agency after just half-season away was a huge win for the organization in more ways than one. Not only was Flaherty great for them before the trade deadline and was still on an upward trajectory after four seasons in decline, it was clear that Flaherty believed in the team and enjoyed his time with them, and that Detroit is becoming an attractive place for free agents.

He signed a contract for one guaranteed year worth $25 million, and it's accompanied by a player option worth $10 million for 2026. In short, he's already looking like he's well worth the price. In five starts, he has a 2.63 ERA, second only to Casey Mize's 2.22 ERA. In his latest start against the Padres, he went six innings and struck out nine batters; the only mistake he made was a hanging curveball that catcher Elias Díaz powered for a two-run homer that eventually won San Diego the game (the Tigers scored zero runs).

If the Tigers keep playing at their current rate, they'll have no reason to deal Flaherty at the deadline again, but they could have some concerns about losing him at the end of the year. Flaherty might like Detroit, but he could end up running his value up, far past the $10 million mark he can opt into next season, which could make him tempted to try free agency again.

There's a simple way the Tigers could get out in front of that: a contract extension.

Jack Flaherty is performing at a level that warrants more than the Tigers' $10 million player option would give him in 2026

The Tigers have money still lying around, given that Alex Bregman turned down their $171.5 million offer in February. It brings up a point that's been hammered home a lot in discussions about a potential extension for Tarik Skubal as well: the Tigers like to talk about how much they want to support and develop the players they already have, so they should put their money where their mouth is.

Offering Flaherty, who is still only 29, another two- or even three-year deal that covers 2026 at a higher rate than he can currently opt into could get the job done. Flaherty is currently performing at the level of a $25 million pitcher — front-loading a new deal with that, or even a little more, while tapering off in the last year could at least entice him.

The Tigers have a lot of momentum now, and there's clearly a lot of goodwill between them and Flaherty. If they can keep him in Detroit for a little longer, it could be huge for the near future of the organization.