Yankees predicted to make blockbuster trade for $400M 2-time Cy Young winner, 2-time All-Star

The New York Yankees entered the offseason knowing their starting rotation would not be fully healthy to begin the 2026 season. Gerrit Cole is expected to miss the first month or so, which could prove costly for New York.

“The New York Yankees have a multitude of needs this offseason, but starting pitching ranks near the top of that list. With both Carlos Rodón (elbow) and Gerrit Cole (elbow) set to miss the beginning of the 2026 season, the club should have at least spot open in their rotation next to Max Fried, Cam Schlittler, Luis Gil and Will Warren,” SI’s Jack Markowski wrote.

At any point, the Yankees could look to make a trade, and one intriguing name to watch is ace Tarik Skubal.

“The Tigers had a rough finish to 2025, particularly on offense, and that's not something Framber Valdez and Justin Verlander will fix. A middling offense and untimely pitching injuries could push the Tigers out of the race and put Skubal on the block. Even as a rental with an enormous salary (he would still be owed about $10 million at the trade deadline), the bidding war for Skubal would be fierce. He's a balance of power player, someone who can swing a division race or a postseason series all by himself,” CBS Sports’ Mike Axisa wrote.

Skubal could potentially seek a way out of Detroit if the season doesn’t go as planned or if the two sides can’t agree on an extension.

“The Tigers and superstar pitcher Tarik Skubal have a lot of work to do if they’re going to bridge quite possibly the biggest gap in MLB negotiating history: an estimated quarter of a billion dollars. Yep, that’s not a misprint. It’s close to $250 million,” New York Post’s Jon Heyman wrote.

The Yankees will need at least one or two arms until their rotation is fully healthy, but Skubal is far from just another addition. He has arguably been the best pitcher in baseball over the last two seasons and would give New York another dominant left-hander.

New York is expected to be a threat once fully healthy, but if they were to trade for Skubal, it would give them a legitimate chance to go toe-to-toe with the Los Angeles Dodgers. Only time will tell, but this would be a massive acquisition.

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