Former Orioles starter may have ruined free agency chances with World Series collapse

All year long, Orioles fans had to listen to the baseball world talk about Jack Flaherty. After the O's acquired him at the trade deadline in 2023, Flaherty collapsed in Baltimore. He was terrible for the team down the stretch and he unceremoniously left for Detroit in free agency last winter.

However, much to the chagrin of Orioles fans Flaherty was dominant with the Tigers in the first half of 2024. The righty pitched to a 2.95 ERA over 18 starts and he was subsequently acquired by the Dodgers at the trade deadline this past summer.

While Flaherty fell off just a touch in the second half, he finished the year with a 3.17 ERA, a 13-7 record, and he notched 194 strikeouts in 162 innings. Prior to joining LA, Flaherty was a popular name in the industry as a potential mid-season acquisition for the Orioles. But for a number of reasons, Baltimore opted not to make a move for him this summer.

Despite his overall strong performance, Flaherty was mostly dreadful in the playoffs with the Dodgers this fall. He had two solid starts but three blow-ups, which amounted to a 7.36 postseason ERA in 22 innings.

How will Jack Flaherty's poor postseason performance affect his impending free agent contract?

Flaherty's final start of the year was in Game 5 of the World Series. The righty allowed 4 runs on 4 hits and a walk, including two homers, in just 1.1 innings. Dodgers' manager Dave Roberts was forced to yank Flaherty in the second inning, leaving him to rely on an already taxed bullpen.

Despite Flaherty's poor performance, the Dodgers wound up coming back in miraculous fashion. The won Game 5, and their second World Series title in the past 5 years, on Wednesday night in the Bronx.

Prior to Flaherty's postseason performance, some experts were suggesting that Flaherty could earn a contract close to $100 million in free agency this winter. More recently, Jim Bowden of The Athletic suggested Flaherty could wind up with a shorter 3-year deal worth $68 million. That would still be a substantial raise over his $14 million salary this past year.

While the small sample of postseason starts isn't necessarily indicative of Flaherty's true talent, it's still possible that his three awful October starts leave a poor taste in teams' mouths this winter and negatively impact his impending free agent deal.

Teams will look at Flaherty as a potential 2 or 3 in their rotation, someone who can and should be starting in the playoffs at his price point. But given that Flaherty now has 47 postseason innings with a 5.36 ERA in his career, that could give teams pause during negotiations.

Ultimately Flaherty will wind up signing a multi-year deal this winter, and he'll probably get a raise over his current annual salary. Whether the team that signs him winds up regretting doing so remains to be seen.