Yankees Named Fit for Potential Nine-Figure Starter in FA

New York Yankees, Jack Flaherty

Getty Brian Cashman looking forward

The New York Yankees took care of business against the Kansas City Royals in Game 3 of the American League Division Series, currently up 2-1 in the series. The Yankees will need to win one of the next two games to advance to the American League Championship Series.

However, whenever the time comes, the Yankees will turn their focus to the offseason. With multiple needs, they could be in the mix for high-level players this winter.

Of those players includes right-handed pitcher Jack Flaherty, who Zachary D. Rymer of Bleacher Report named the Yankees a “potential fit” for.

“Fueled by a reinvigorated fastball and one of the better curveballs in the league, the righty finished in the top 10 among qualified starters in strikeout-to-walk ratio. He gave up three earned runs or fewer in 23 of his 28 starts.

“Flaherty did have some back issues in the middle of the season, and he seemed out of gas by the end of it,” Rymer wrote on October 10. “The worst fastball velocity he had all year was in his last two starts. This wasn’t totally unexpected, however. Nor is it necessarily a five-alarm fire. Flaherty will only turn 29 on October 15, making him relatively young for a high-upside free-agent pitcher.”


Flaherty Could Get Nine-Figure Deal Depending on Postseason Performance

Flaherty, 28-years-old, has had an up-and-down past few seasons. Spanning between the 2022 and 2023 seasons, Flaherty posted a 4.84 ERA, 4.48 FIP, 88 ERA+, and struck out 181 hitters in 180 1/3 innings pitched, which could worry the New York Yankees.

However, in 2024, he’s been as good as it gets, posting a 3.17 ERA, 127 ERA+, 3.48 FIP, and struck out 194 hitters in 162.0 innings pitched.

Despite turning it around, his prior struggles could still hurt him in free agency.

Kiley McDaniel of ESPN believes Flaherty “has helped his stock” but is still playing for more money in October with the Los Angeles Dodgers. McDaniel listed free agents who still have something to prove in the postseason and had Flaherty in the “playing for a nine-figure payday” section.

“Flaherty has helped his stock with a bounce-back season coming at the right time after four straight middling campaigns. His best free agent comps both happen to be pitchers from the 2021-22 free agent class: Kevin Gausman (five years, $110 million) and Robbie Ray (five years, $115 million). Projecting his next contract requires some adjustments from those starting points due to natural market inflation over three years and Flaherty being younger than both with a slightly better platform season — but a shorter track record of success leading into free agency.

“This is where October comes into play. If Flaherty can rebound from his up-and-down NLDS Game 1 start against the San Diego Padres, a series of standout playoff outings (if the Dodgers advance far enough) might help teams feel better about him repeating his 2024 season,” McDaniel wrote on October 9. “But if he doesn’t get that chance or shows more of the same, teams could be wary of spending well past $100 million.”


Yankees Had Interest in Flaherty at the Deadline

The New York Yankees were interested in Flaherty at the trade deadline and ended up as one of two finalists to acquire him. The California native was traded to the Los Angeles Dodgers, giving them an added boost to their postseason push at the time.

According to Jorge Castillo of ESPN, Brian Cashman said the Yankees couldn’t match an offer that made sense for them.

“At the end of the day, I would’ve brought Jack Flaherty in if I could’ve matched up, and I had difficulty matching up,” Cashman said in July. “And that was the reason I don’t have him.”

However, the Yankees’ prior interest could be an indication that they’ll inquire about him in the offseason.

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Yankees Named Fit for Potential Nine-Figure Starter in FA

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