Two of the biggest storylines for the New York Yankees this offseason were what they would do with manager Aaron Boone and ace Gerrit Cole's contracts. Even after a disastrous World Series performance, the Yankees exercised Boone's 2025 option and were able to work out an agreement for Cole to remain with the team after he briefly opted out.
Yankees owner Hal Steinbrenner addressed both Boone and Cole's futures with the team to Gary Phillips of the New York Daily News on Wednesday.
“Hal Steinbrenner left the door open to adding onto Aaron Boone and Gerrit Cole's contracts,” Phillips wrote. “Nothing imminent, though.”
Boone's contract will be up after this season. After re-negotiating his contract after opting out, Cole will stay with the Yankees on a four-year, $144 million contract,
While Yankees fans may be focused on whether or not Steinbrenner is willing to pay up to keep superstar free agent Juan Soto in the Bronx, these potential moves are also crucial to the future of the Yankees organization.
Should the New York Yankees extend Aaron Boone and Gerrit Cole?

While it would have been shocking to move on from a manager who brought his team to the World Series, Boone's poor decision-making in the postseason and the Yankees' defensive and base-running miscues could have been enough of a reason for Cashman to justify a change. However, there is no guarantee that the next potential manager would have been able to do a better job, especially in an environment like New York.
Even though the Yankees brought Boone back for the 2025 season, it would not be a surprise, even with Steinbrenner's comments, if the Yankees take a serious look at whether or not to offer Boone a long-term contract. If a better managerial candidate becomes available, a move could make sense.
In Cole's case, it absolutely makes sense for the Yankees to consider an extension. While they may not have wanted to add on that extra year at the price he was asking for earlier this offseason, if they are able to come to an agreement on a longer-term, lower-AAV extension, that could be appealing for both sides.
Cole, who won the Cy Young award in 2023, is 34 years old now and just came off a season where he dealt with a significant elbow injury. While he was still effective, it is safe to assume that he will experience some regression from now until the end of his contract in four years. But, Cole is still an ace, and the Yankees should do everything they can to keep him around.
There is no reason for Steinbrenner not to float the idea of an extension for two of the organization's most important figures. But, it is not a guarantee that they will both be around long-term after the 2025 season, especially if Boone is not able to fix some of the Yankees' fundamental issues that plagued them during the World Series.