About the Off-Season: Settling In For a Long Winter

About the Off-Season: Settling In For a Long Winter

By Tim Kabel

October 10, 2025

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Yesterday, the Yankees had their first day off in what will be an exceptionally long string of days off. The Yankees’ season ended much earlier than any of us hoped or wanted. It did not necessarily end earlier than many of us expected. The Yankees now join the ranks of the also-rans as the 2025 season draws to a conclusion. That conclusion will not include the Yankees winning a World Series, yet again.

The Yankees have a storied tradition. They have 27 World Championships. That is more than any other team. However, they have not won the World Series since 2009. That was 16 years ago. Aaron Boone has been the manager for eight seasons. Although he waxes poetic about how everything is “right in front of” the Yankees, right now everything is behind them. They're done. Boone said this was the best team he ever managed. Yet they were bounced in the Divisional Series by the Blue Jays. Not only were they jettisoned, but they were also humiliated. In the first two games, the Yankees gave up more runs in a two-game stretch in the postseason than any other team in Yankees’ history. Yes, the team that Aaron Boone said is the best team he has ever managed committed an act so ignominious that they stand alone in the annals of ineptitude.

In addition to being slapped around on the field by the Blue Jays, they were also scorned and ridiculed by the Blue Jays’ manager and Vladimir Guerrero, Jr., among others. David Ortiz, a veritable bastion of class and good manners was right there with Vladimir Guerrero, mimicking John Sterling to rub salt in the Yankees’ wounds. The worst part about that is that there is nothing the Yankees can do about it. They put themselves in this situation and they don't look as if they have a plan to get out of it. The Yankees have not been the best team in baseball in 16 years. If you were born at the last time the Yankees won the World Series, you could get a driver's license and drive to the stadium and watch them lose in the playoffs now.

In the past, George Steinbrenner, Billy Martin, and even Derek Jeter and his teammates, would not have tolerated the ridicule that was heaped upon the Yankees after Wednesday's loss. They would have done something about it. I'm sure it must have been torture for Jeter to stand there, listening to Ortiz and Vladimir junior. We all know that George Steinbrenner would have exploded. There would have been all sorts of changes made. Unfortunately, George Steinbrenner is long gone. In his place, we have Hal, who will simply purse his lips and look disappointed. He will say something about not wishing to put up with this, but he will do nothing other than make a few moves that are little more than window dressing. At least that's what has happened in the recent past.

Now that the Yankees have been eliminated, we will have a lot of time to discuss what went wrong and what needs to be done before this team takes the field in 2026. The Yankees have several players who will be or could be free agents. Decisions need to be made by the Yankees and those individual players as to whether they will return. There are other players and positions that need to be scrutinized to determine what should be done for next year. We will do all of that.

We will also look at whether Brian Cashman and Aaron Boone should return and whether they will return. Those are not necessarily the same things.

First and foremost, we need to acknowledge that even though the Yankees won 94 games, this season was a disappointment. The Yankees benefited from a schedule that had them play the weakest teams in the league at the end of the season. Playing the Orioles, White Sox, Nationals, and Twins made the Yankees strong finish to the season much more likely. However, it also made it a mirage. Many of us believed that based on the strong finish the Yankees had, they would storm through the postseason. They didn't. This team had a losing record in both June and July and went from leading the American League East by 7 games on May 30th to being tied for first place with the Blue Jays at the end of the season. Because the Blue Jays won the season series against the Yankees, they won the division and had home field advantage.

The fact that the Yankees played horribly against the American League East was one of their main problems this season, but it wasn’t their only problem. The Yankees were streaky and unpredictable this season. They were not unpredictable in a good way. They were unpredictable in a bad way, as in unreliable. The only thing you could really predict about them is that when you most needed them to be a championship caliber team, that's when they were least likely to do so. Yes, they avoided a sweep at the hands of the Blue Jays but on Wednesday night they resumed playing sloppy ,fundamentally weak baseball. They did not put up much of a fight against the Blue Jays on Wednesday night, other than Aaron Judge and Jasson Dominguez in his cameo appearance in the ninth inning.

This was the latest in a 16-year string of disappointing seasons for the Yankees. In future articles, I will look at what needs to be done to this team so that we are not gathered together again next October lamenting yet another early departure from the postseason for the Yankees.

For today, we will simply wallow in our disappointment and discouragement and accept the fact that the 2025 Yankees were not good enough. If you are planning to tell me that they were good because they won 94 games, let me ask you this, when was the last time any city had a ticker tape parade for a team that lost in the Divisional Series? The answer would be never. Right now, never seems to be about the time the Yankees will win their next World Series.