Tigers' connection to Jack Flaherty in free agency ignores one major problem

Everybody loves a good reunion in sports, but a potential one between Jack Flaherty and the Detroit Tigers is one that comes with a red flag so large it outweighs all of the green flags.

Flaherty, 29, made 18 starts for the 2024 Tigers before being traded to the Los Angeles Dodgers at the deadline and continuing to be a well above-average pitcher. During his time in Detroit, the right-hander made some of the best starts of his eight-year career and easily looked as sharp as he's been since his breakout 2019 campaign.

During the 2024-25 offseason, the Tigers have been linked to various free agents on both the position player and pitcher side of things. The club has a handful of glaring needs to address this winter, but upgrading their starting rotation has to be near the top.

To their credit, the Tigers have already signed aging veteran Alex Cobb to a single-year pact, but there's still room for another starter alongside him, Cy Young winner Tarik Skubal, 25-year-old Reese Olson, and one of Casey Mize or Jackson Jobe. Flaherty remains squarely on the Tigers' radar, but is he going to be worth it with his rumored contract demands?

Jack Flaherty's rumored contract ask may complicate a Tigers reunion

Flaherty ultimately finished this past season with a 3.17 ERA across 28 starts, striking out nearly 11 batters per nine innings and putting together a 127 ERA+ that puts him 27 percent better than league average on the bump. He's in line for a major payday and a well-deserved one, too.

However, Will Sammon and Katie Woo of The Athletic recently reported that Flaherty is seeking a deal of "at least five years," which should be a major turn-off for the Tigers, who are not keen on offering those types of contracts under Chris Illitch. While Flaherty's still just 29 years of age, he's also only had one solid season since 2021 and has struggled mightily with his durability over the years.

There will absolutely be a team out there that's willing to overpay for Flaherty solely based off of his output from this past season, but the Tigers don't have the room for a bad decision like that. The reality is that Flaherty has been a very hot-and-cold pitcher over the years, and has only been a "great" pitcher in 2018, 2019 and 2024. Over an eight-year span, that's not enough of a lengthy track record to suggest he's worth a half-decade commitment.

As MLB.com's Mark Feinsand reported on Friday, the Blue Jays, Cubs and Giants are the other three teams "remaining in the mix" for Flaherty, alongside the Tigers. The competition is still fierce, so Detroit would be better off sitting this one out unless the right-hander is willing to take a shorter deal with a higher AAV from his former club.