The New York Yankees held their annual postmortem press conference to commemorate another season where the organization fell well below expectations. Despite their shortcomings, Cashman used the word “proud” to describe a tumultuous up-and-down 2025 season, which saw a division collapse and two months of sub-.500 baseball during the summer.

“We’ve had success and failure. We had a good team, but fell short of our ultimate goal,” Cashman said, with a bottle of water in hand as he fielded questions from the press scrum at Yankee Stadium. “I’ll leave it for the masses to debate what ultimately came out of it. Proud of a lot of things we accomplished.”

“Proud” could have been a way to describe the 2017 team. In a rebuilding year, those Yanks took the Houston Astros to game seven of the American League Championship Series, but in year nine of the Aaron Judge era, it’s a word that resembles little of what the organization should have felt the night they were eliminated by the division rival Blue Jays.

The vibes at Yankee Stadium mirrored the vengeful celebration of the Red Wedding in Game of Thrones. Covered in champagne, their AL East rival’s spiteful revelry in the opposing locker room involved blasting New York, New York, all while Vladimir Guerrero Jr. and David Ortiz said in unison on Fox, “Daaaa Yankees Lose.”

Why No One Should Be Proud

It’s easy to fantasize about a world where the Yankees are unsettled by what the Blue Jays did to them at home and they react with a big off-season. However, it seems that no matter how many disappointing losses they face, the necessary moves to get them over the hump are never made.

If they do bring in a Gerrit Cole, Max Fried, or Juan Soto, the follow-up acquisitions afterward tend to be disappointing. Cashman will call the Yankees the “Mecca” after every big move, and yet, the new stars are surrounded by the Marcus Stromans and Alex Verdugos of the world.

When Cashman speaks positively of the season, it could be that the organization is happy with the results at hand. The expectations have shifted, and George Steinbrenner’s winning mantras have been relegated to old episodes of Yankeeography. Yes, they lost to the Blue Jays, but it was another .500 season, where they managed to have a few postseason gates as well. That could be the new goal, which is a diluted reality from what fans are sold before every season starts, and they need seats filled over on River Avenue.

While Hal Steinbrenner could not make the presser, Cashman did speak on his behalf. According to the GM, the owner of the team apparently did not view the season through rose colored glasses.

“He’s frustrated, disappointed,” Cashman said of his boss. “He wants a championship here for him and his family. They believed, many times, that we had a chance to do something.”

If all that is true, the Yankees have another chance this winter to add the proper personnel for a 28th championship. Whether they do remains to be seen. It’s fair to be skeptical at this point.

Make sure to bookmark Yankees On SI to get all your daily New York Yankees news, interviews, breakdowns and more!