On one hand, it’s hard to blame the Yankees for welcoming back 2023 American League Cy Young Award winner Gerrit Cole this offseason. On the other, if you gave New York truth serum right this minute, it might take the mulligan.

The Yankees’ hopes to get back to the World Series in 2025 took a major hit three weeks before Opening Day, with New York announcing Monday that Cole will undergo season-ending Tommy John surgery. The former Cy Young winner was set to go under the knife Tuesday.

The development came just a couple of short months after the Yankees essentially obliged Cole’s request to lengthen his contract. He used his option to opt out following the 2024 season, and the Yankees technically could have let Cole walk in free agency. Instead, the Yankees and Cole reconvened, and the big right-hander remained in the Bronx under the parameters of his original nine-year, $324 million contract.

Now, Cole has four years and $144 million ($36 million per season) left on that deal. He won’t pitch in 2025, and he could miss a chunk of 2026. There are no more opt-outs, and the deal will run through the 2028 season when Cole will be 37. If there’s any sort of financial silver lining for the Yankees, as ESPN’s Buster Olney pointed out, is that the club does have insurance on the deal which will help offset some of the money owed to an injured Cole.

It would have taken an extremely calculated, bold decision for Brian Cashman and the Yankees to walk away from the Cole deal. However, this isn’t a major shock, either. Cole missed a chunk of the 2024 season with elbow issues, obviously a precursor to what followed. His production dipped, too, at least relatively, with Cole going 8-5 with a 3.41 ERA in 17 starts for New York last year. He pitched well in the postseason, too, his final start notwithstanding. Cole allowed fewer than three earned runs in each of his five starts but was erratic at times.

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The Yankees ultimately fell short in the World Series, bowing out in five games to a loaded Los Angeles Dodgers team. While New York did add Max Fried in the offseason, the Cole injury is a major blow to a rotation with a few question marks as it is.

With the Red Sox making huge strides over the winter and a team like the Orioles one year later into their ascension, it’s possible New York missed its best chance to win its first title since 2009.

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