t’s going to be an interesting offseason for the New York Yankees after they failed to meet expectations once again in 2025. With Aaron Judge leading the way, it’s World Series or bust for the Yankees every year at this point, and with each passing season they are unsuccessful in their quest to win it all, the pressure on the team rises.

The calls for Aaron Boone and Brian Cashman’s heads are continuing to grow louder, but New York is sticking with both guys as the team heads into the 2026 campaign. How the offseason unfolds, though, could determine just how much longer they spend in town. Last week, the team made one of its first notable moves when it stole a pitcher from the Boston Red Sox in free agency.

Yankees Steal Yovanny Cruz from Red Sox

The 2025 season followed a similar path for New York. Despite being one of the best teams in the league during the regular season, they couldn’t carry their success over to the postseason. While the Yanks managed to get past the Red Sox in their wild-card matchup, they eventually bowed out in the ALDS after losing in four games to another American League East rival, the Toronto Blue Jays.

With the offseason now upon us, there are several needs the Yankees will be looking to address. Finding a more consistent option at third base could certainly be helpful, and adding some arms to both the starting rotation and bullpen appears to be a possibility as well. If New York pushes the right buttons over the next couple of months, it could conceivably emerge as a top World Series contender in 2026 and beyond.

Sometimes, though, the flashy moves aren’t the most important moves a team can make in the offseason. Adding depth pieces that may not appear likely to contribute is sometimes the difference between winning it all and coming up short in the postseason. With that in mind, the Yankees’ recent signing of Yovanny Cruz in free agency caught the attention of fans.

“New York Yankees signed free agent RHP Yovanny Cruz to a minor league contract,” the team announced last week.

Yankees Looking to Be Aggressive During Offseason

GettyNew York Yankees general manager Brian Cashman

It shouldn’t come as much surprise that the signing of Cruz doesn’t jump off the page. He has never pitched in the majors, as he spent the entire 2025 campaign at Double-A for the Red Sox. Cruz appeared in 34 games, posting a 2-4 record with a 3.64 ERA, 72 strikeouts, and six saves. While he’s already 26 years old, he does have some upside that New York could look to tap into.

Expectations aren’t going to be high for Cruz, and if he makes any sort of contribution at the major league level in 2026, that will be considered a win for the Yankees. While hurting its longtime rival is always nice, New York will be more interested in swinging some bigger moves in the coming weeks. With the Yanks getting linked to just about every player available,