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Cardinals Fans Shouldn't Get Their Hopes Up for Jack Flaherty Reunion

Jack Flaherty is a free agent, but if Cardinals fans were expecting a reunion, think again.

Jul 4, 2026; Arlington, Texas, USA; Detroit Tigers starting pitcher Jack Flaherty (9) pitches against the Texas Rangers during the fourth inning at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | IMAGN IMAGES via Reuters Connect

The St. Louis Cardinals will likely be looking to add a starting pitcher on a "prove-it" deal this offseason, not unlike what they did with Dustin May last year. May could be the one they decide to sign again, but there are certainly other options. One that Will Leitch of MLB.com floated was right-hander Jack Flaherty.

Flaherty was with the Cardinals from 2017-23 and even received Cy Young votes in 2019, but injuries have been a problem for him ever since. Still, he does have upside that could benefit the Cardinals.

However, former Cardinal Lance Lynn doesn't think it's a good idea to bring him back.

"The question you have to ask yourself on Jack is, there's a reason why he keeps getting one-year deals and there's a reason why you traded him when you traded him," Lynn said. "Is bringing that back in going to be good for what you're building, or will it be a problem? I like Jack, he's had great stuff when healthy and doing his thing, but all of that coaching staff is still there from when he got traded. He got traded for a reason. I don't think it's a fit to be honest with you."

Cardinals fans shouldn't cross fingers for Jack Flaherty reunion

Jun 12, 2026; Cleveland, Ohio, USA; Detroit Tigers starting pitcher Jack Flaherty (9) throws his first pitch of the game during the first inning against the Cleveland Guardians at Progressive Field. Mandatory Credit: Scott Galvin-Imagn Images | IMAGN IMAGES via Reuters Connect

Lynn alluded to there potentially being some bad blood and went on to say that he doesn't expect "a kumbaya, big warm hugs" if he returns to St. Louis.

The difference now is that the front office is led by Chaim Bloom and not John Mozeliak, so there have been some changes, but perhaps Flaherty would prefer to pitch for a contending team.

His injuries certainly don't help his case, and while that was the case with May, he at least was close to figuring everything out, and he finally was healthy for a full season in 2026, so he may be their best option to bring back.

He also has helped the Milwaukee Brewers in their quest for a World Series title, so there's more of a positive track record there than there is with Flaherty. Flaherty is also over 30 years old, so there is probably more risk than reward if the Cardinals are thinking about bringing him back.

So, it will be interesting to see what Bloom is thinking as far as adding a starter. Flaherty could be a candidate for a "prove-it" deal, but likely is not the best fit for what the Cardinals are trying to do.

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