The Kings of October, that’s what the baseball fraternity calls the NYY, as they have won 27 World Series rings. But the last time the Bronx held the October glory was back in 2009. A drought of 16 years. Every summer, they somehow fall short. Remember that gut-wrenching loss to the Dodgers in the 2024 World Series? And this season? The Yankees, who finished with 94 wins, met their fate in a 5-2 loss to the Blue Jays in ALDS Game 4. Now, after weeks, Aaron Boone came in front of the mic and didn’t hold back, sharing which loss stings more!

In a recent podcast, Aaron Boone drew the sharp contrast between this year’s disappointment and the 2024 World Series loss to the Dodgers. When asked about it, he straightaway confessed it, “This one’s more kind of lasting pain a little bit more.” Well, what made this loss particularly difficult was the timing and the belief he held about his roster. “I really felt great about our team,” he explained. “We went through a lot this year as a club, but by the end, we’re healthy, we’re playing well.”

He compared it to 2022, when the Yankees arrived at the championship series already depleted. That summer, they dominated early with a 61-23 record and a commanding 15 1/2-game division lead, only to exit the playoffs with a 3-7 record against Cleveland and Houston. The momentum vanished when it mattered most. “We’re kind of spent by the championships and we’re broke. We lost some key guys,” Boone recalled.

And once again he repeated, “This one was as painful as any of them. It’s here three weeks later and it’s still like, damn.”

The season itself tested them constantly. Their bullpen struggled to find a rhythm, with relievers often rotating in and out of high-pressure situations. Injuries destabilized the rotation throughout the summer. In his second year, Anthony Volpe faced growing pains, forcing the team to frequently adjust its lineup and defense. While he showed flashes of talent, he lacked the consistency he had in his first season, adding to the team’s challenges.

Aaron Boone acknowledged his own second-guessing in managing those problems. “I kind of feel like I wish I would have maybe had a little more conviction with some pen decisions in the middle of the year,” he admitted. “We didn’t have the matchups we would normally want. It was like I was putting guys in some spots where maybe I should have had the courage to just go with this guy that doesn’t have the track record yet.”

Now that 2025 is over with the Dodgers winning the World Series for the second time, the Yankees must focus on a few areas that need to be addressed to help Aaron Boone & Co. avoid yet another painful playoff loss.

Yankees offseason game plan for 2026

The NYY have a very important offseason in 2026, and as per reports, many big changes are supposed to happen that will help them meet their needs and stay flexible in their strategy.

Cody Bellinger and another experienced outfielder, Trent Grisham, will be free agents soon. As per the reports, the clubhouse must re-sign Bellinger. Why? Well, he adds left-handed power, the ability to play center field, and a bounce-back season that fits their lineup. The Yankees are in a good position to make his return a priority instead of going after a more expensive outside option because he can play many positions and keep costs down.

Kyle Tucker is the top position player in free agency, and the Yankees are showing strong interest. They need another elite bat and are prepared to invest heavily. Acquiring Tucker would enhance their lineup and signal a commitment to compete aggressively in 2026, despite the substantial financial commitment required.

The Yankees still want to improve their rotation, and Skubal has come up as a possible trade target. Adding him would give New York a top-notch pitcher who could lead the staff. This bold prediction sees a big trade package to bring in an ace-caliber starter, based on their needs and his standing with the Detroit Tigers.