The Detroit Tigers struck gold when they signed starting pitcher Jack Flaherty to a one-year contract during the offseason ahead of the 2024 campaign.

He performed at such a high level that the team was able to flip him before the trade deadline in exchange for two highly-touted prospects; shortstop Trey Sweeney and catcher Thayron Liranzo.

After helping the Los Angeles Dodgers win the World Series, many thought Flaherty was in line for a multi-year deal. Unfortunately, those offers never materialized and the Tigers were able to take full advantage once again.

They brought him back for the second free agency in a row, agreeing to a two-year, $35 million contract, the second year of which is a player option.

Should things go well for Flaherty during the 2025 season, he will have the opportunity to opt out of his deal and seek the lucrative long-term contract he desires.

Jeff Passan of ESPN believes it is possible the veteran right-handed pitcher will cash in, listing him amongst the contenders to land a nine-figure deal in free agency this upcoming winter.

Part of the hesitancy from teams around the league to sign Flaherty long-term could have stemmed from wanting to see him repeat his performance.

He was stellar in 2024, but in three out of the previous four seasons, his production wasn’t great and he struggled at times to stay healthy.

In both areas, he has been solid through his first seven stars of the year.

Flaherty has a 3.79 ERA across 38 innings with 46 strikeouts. Not quite as dominant as his tenure with the Tigers in 2024, but more than serviceable.

His whiff and strikeout rates remain excellent, and he has shown the ability to be a true frontline starter in the past. So if he can stay healthy, a $100 million offer this winter is certainly within the realm of possibility.

Given how much money teams are willing to commit to pitchers, Flaherty should opt out with a solid season and finally cash in.