Did Yankees' Gerrit Cole opt out knowing he needed Tommy John surgery?

When Gerrit Cole exercised the opt-out clause in his contract with the New York Yankees last November, speculation swirled about whether he would leave for a bigger deal. 

But days later, he and the Yanks agreed to reinstate the original contract — an unusual turn of events that required MLBPA approval. Now, with news that Cole will undergo Tommy John surgery and miss all of 2025 and most of 2026, the timing of his decision raises questions.

Cole’s opt-out wasn’t a unilateral decision. It wasn’t simply a case of him opting back in alone. Instead, he and the Yankees worked out a mutual agreement to restore his existing deal, a process that required league approval. Unlike other players who use opt-outs to test free agency, Cole never actively shopped himself to other teams. He has consistently stated that playing for New York was always his goal, and sources indicated he was not looking to sign elsewhere.

Cole had been dealing with elbow discomfort since the beginning of the 2024 season. He missed all of April and May before returning in mid-June. While he pitched well upon his return, his elbow issues persisted into the offseason and eventually flared up again this spring, leading to the decision to have Tommy John surgery.

Given that teams perform extensive medical evaluations on free-agent pitchers, it’s fair to wonder whether Cole and his agent, Scott Boras, recognized that surgery was a real possibility. If Cole had hit free agency, would teams have been willing to match the $144 million remaining on his deal, knowing he might need a year (or more) of rehab? By working with the Yankees to reinstate his contract, Cole ensured he would remain with the team he wanted to play for while securing his long-term payday.

For the Yankees, retaining Cole was always the preferred outcome. Losing their ace without a straightforward replacement would have been disastrous, and there was no reason to let negotiations drag into the offseason. However, with the benefit of hindsight, they now find themselves in a tough spot — paying $36 million for a lost season while scrambling to fill a massive void in their rotation.

Cole’s decision to remain in New York wasn’t about chasing a more significant contract or leveraging the opt-out for more money. Instead, it was a mutual agreement between him and the Yankees to maintain the status quo — an arrangement that, at the time, seemed beneficial for both sides. With Tommy John surgery sidelining him for all of 2025, it’s worth considering whether Cole and Boras anticipated this scenario.

Ultimately, Cole got what he wanted: stability, security and the chance to continue pitching for the team he’s always dreamed of playing for. Whether the Yankees will regret their role in this deal remains to be seen.