The righthander has had an up-and-down career.

Jack Flaherty was a first-round pick of the Cardinals (34th overall) in 2014 out of a very famous baseball high school, Harvard-Westlake in Los Angeles. Other successful pitchers (Max Fried, Lucas Giolito) attended that school. So did Pete Crow-Armstrong, as you probably know.

Flaherty had some good years in St. Louis and then the injury bug hit. Mostly, it was shoulder problems, but he also missed time in 2021, 2022 and 2023 with oblique and hip injuries.

Healthy in 2024, Flaherty split the year between the Tigers and Dodgers and pitched well in both places, winding up with a 3.17 ERA, 1.068 WHIP and 3.1 bWAR.

That would seem to be a good time for a pitcher to hit free agency, especially at the relatively young age of 29 (Flaherty turned 29 in October). Comparison point: Flaherty is three months younger than Justin Steele.

So should the Cubs look at Flaherty in free agency?

MLB Trade Rumors says Flaherty will get a deal for five years and $115 million. That’s not an unreasonable deal ($23 million AAV) for a pitcher of this age and ability.

Caveat, from the MLBTR analysis:

There could be some questions about his health over a long-term deal. Beyond the previously noted shoulder injuries that hampered him earlier in his career, there were concerns about the health of his back leading into the trade deadline. The Yankees reportedly reached a preliminary agreement on a deal to acquire Flaherty but nixed the trade after reviewing the right-hander’s medical records. That eventually led Flaherty to instead be traded to the Dodgers for what some at the time considered a light return.

So, there’s some risk here as well, though Flaherty made it through 28 starts and 162 innings in 2024 without incident, and also made five postseason starts (though the results, a 7.36 ERA, 6.71 FIP and six home runs allowed in 22 innings, weren’t great).

Should the Cubs look into signing Flaherty at this price? Or try to get him on a different deal? I’m kind of ambivalent here. This would be a medium-risk, high-reward type of signing. If Flaherty stayed healthy, it could be a very good signing. If not, well… the torches and pitchforks line forms to the left.