Inside The Cardinals

Could Cardinals Pursue Reunion With $35 Million Pitcher In Free Agency?

The Cardinals could be aggressive in the winter...
Zach Pressnell|
Aug 24, 2025; Detroit, Michigan, USA; Detroit Tigers pitcher Jack Flaherty (9) throws during the first inning against the Kansas City Royals at Comerica Park. Mandatory Credit: Brian Bradshaw Sevald-Imagn Images
Aug 24, 2025; Detroit, Michigan, USA; Detroit Tigers pitcher Jack Flaherty (9) throws during the first inning against the Kansas City Royals at Comerica Park. Mandatory Credit: Brian Bradshaw Sevald-Imagn Images | Brian Bradshaw Sevald-Imagn Images

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St. Louis CardinalsDetroit Tigers

Major League Baseball had one of the more exciting years in recent memory over the last calendar year. Free agency was very exciting during last offseason, headlined by the massive Juan Soto sweepstakes. There were also massive trades made in the winter months.

But the upcoming offseason could be as exciting as ever, especially if a lot of the top potential free agents opt out of their current contract.

MLB's Mark Feinsand recently suggested that Detroit Tigers pitcher Jack Flaherty would opt out of his contract at the end of the year. If he lands in free agency, there's a chance he could pursue a three or four-year contract.

Cardinals could reunite with Jack Flaherty in free agency

Detroit Tigers pitcher Jack Flahert
Aug 1, 2025; Philadelphia, Pennsylvania, USA; Detroit Tigers pitcher Jack Flaherty (9) throws a pitch during the fourth inning against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | Bill Streicher-Imagn Images

"Flaherty signed a two-year, $35 million deal with the Tigers in February, paying him a $5 million signing bonus and $20 million salary in 2025," Feinsand wrote. "He reached the requisite 15-start plateau to double his 2026 salary from $10 million to $20 million, though he can opt out of the deal after the season to give free agency another try. Flaherty is 7-13 with a 4.87 ERA in 26 starts this season, so the way he finishes the year will influence his contractual decision."

If Flaherty lands in free agency, the St. Louis Cardinals could look to reunite with their former star pitcher to help boost their roster going forward.

St. Louis is undergoing a bit of a rebuild right now, but that doesn't mean they won't be aggressive in free agency.

St. Louis needs to add a pitcher to its roster. With Erick Fedde gone and Miles Mikolas soon to follow suit, the Cardinals are down a few pitchers. There are some top talents in the farm system like Quinn Mathews and Tink Hence who could be up in the big leagues by next season, but adding one veteran pitcher on a two or three-year contract wouldn't be a bad idea.

The Cardinals likely wouldn't be the top suitor in the Flaherty sweepstakes, but they could be a dark horse candidate. Either way, the Cardinals could make a run for a reunion and it would make a lot of sense.

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Zach Pressnell
ZACH PRESSNELL

Zach Pressnell has experience covering all major US sports at both the professional and collegiate levels. He’s produced content for FanSided, Blog Red Machine, The Game Haus, Bethany College Athletics and the Bethany College online newspaper, He graduated from Bethany College (WV) with a degree in Communications and Media Arts, specializing in Sports Journalism. Pressnell was also a four-year member of the baseball team where he earned himself All-PAC recognition as a pitcher (and a cool Tommy John surgery scar). Now, Pressnell specializes in NFL and MLB coverage for Sports Illustrated’s “On SI” network among others. For all business/marketing inquiries regarding "St. Louis Cardinals On SI," please reach out to Scott Neville: scott@wtfsports.org

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