The Yankees have their sights set on the perfect addition to their starting rotation

Jack Flaherty is coming off one of the best seasons of his up-and-down career. The new free agent helped the Los Angeles Dodgers win the 2024 World Series after getting traded from the Detroit Tigers, going went 6-2 with a 3.58 ERA across 10 regular-season starts with L.A. Flaherty ran hot and cold during the playoffs, but considering his 2024 as a whole and how good he is when he's on, he has to be considered one of the best available pitchers this offseason. And according to ESPN’s Jeff Passan, one team in particular is keenly interested in the Flaherty sweepstakes: the New York Yankees.

Gerrit Cole missed a lot of time due to injury in 2024. He’s 34 years old, and his best years are certainly behind him. The veteran still wants to win a World Series in pinstripes, and he certainly can. But New York’s window is starting to close, as Cole and Aaron Judge are in the later years of their prime right now, and the World Series underlined the fact that reinforcements are needed.

Cashman wanted those reinforcements to be Flaherty, reportedly agreeing to a deal with Detroit at this year's trade deadline before backing out over concerns about the righty's balky back. After watching him finish the season healthy, however, New York might be ready to seal the deal this time — and doing so should be a priority this winter.

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Yankees need to add depth to 2025 starting rotation

Plans A, B and C for the Yankees are to re-sign Juan Soto, but no matter what happens with the superstar outfielder, the team will still need pitching. Carlos Rodon hasn’t pleased fans in the Bronx, Nestor Cortes is coming off an elbow injury, Clarke Schmidt missed a lot of time with injuries of his own and Luis Gil struggled in the second half of 2024. 

When Flaherty is on, he’s on. This past season, he posted a 3.17 ERA across 28 starts. His 10.8 K/9 was third in all of MLB. He would be a perfect piece in Aaron Boone’s rotation behind Cole. And because of his checkered injury history, it might not take much to sign the 29-year-old, as Jim Bowden of The Athletic predicts he’ll get a three-year deal. 

A rotation of Cole, Flaherty, Rodon, Cortes and Schmidt or Gil could be lethal. Signing the World Series champion would be a great idea, as the window with Judge and Cole is closing. With or without Soto, they could use an extra arm like Flaherty, especially with all the flaws in the Yankees starting rotation. In 2025, Cashman can get New York back to the World Series. They still have a great team, but Flaherty could be the missing piece the rotation needs.