Different year, same ending. Once again, the New York Yankees had a strong regular season (but not strong enough to win the AL East), dismantled the Boston Red Sox in the Wild Card series, and got embarrassed in the ALDS against another division rival. They lost in four games to the Toronto Blue Jays in the 2025 ALDS, and lost this season to the Tampa Bay Rays in three games.
Getting to the playoffs hasn't been an issue for the Yankees, as they've done so nine times in the last 10 years. They've made the playoffs 13 times in 17 years since winning the World Series back in 2009. They do deserve credit for that, but making the playoffs isn't good enough, though. At least it isn't supposed to be for the franchise with 27 World Series rings. Yet, that's all they've accomplished since 2009. Given the fact that they keep losing early, and in the exact same way, something has to change, right?
At some point, postseason results can't be seen as random
I understand that anything can happen in a short series, especially in a best-of-five round. No, I don't think the Rays were that much better than the Yankees. How do you explain the exact same thing happening every single year, though?
Again, it's been 17 years since the Yankees last won a World Series. The 2026 campaign was Aaron Boone's ninth year as Yankees' manager, and while he's consistently gotten his teams to October, they've had a brutal time advancing when the lights are bright. They've won a total of one Pennant in Boone's tenure, before getting embarrassed in five games by the Dodgers. What hurts even more is that they keep losing in the same way.
Year | Round | Opponent |
|---|---|---|
2026 | ALDS | Rays |
2025 | ALDS | Blue Jays |
2024 | World Series | Dodgers |
2023 | Missed Playoffs | N/A |
2022 | ALCS | Astros |
2021 | Wild Card | Red Sox |
2020 | ALDS | Rays |
2019 | ALCS | Astros |
2018 | ALDS | Red Sox |
Do you notice a theme here? This list of teams omits one American League division: the AL Central. The Yankees have had their way with teams like the Guardians, Twins and Royals in the playoffs, but other than the Red Sox in the past two Wild Card series, what non-Central team have the Yankees beaten?
Even beyond that, what higher-seeded team have the Yankees beaten? When was the last time the Yankees won a single road playoff game against a non-AL Central team? To answer these questions, the only higher-seeded team the Yankees have beaten under Boone are the Guardians (AL Central) in the 2020 best-of-three Wild Card series, and their last road playoff win against a non-AL Central foe came in the 2019 ALCS in Houston.
The Yankees continue to fall flat on their faces whenever they face any sort of adversity. They don't just lose in the postseason, they do things like score five runs in three ALDS games and commit four errors in Game 2. They embarrass themselves every October. There's only so much Boone can control, but is that not a bad look on his end? Does Brian Cashman still not think any major changes need to be made?
It's time for another Brian Cashman big offseason swing
A way to get guaranteed change would be firing Cashman, but it feels as if he has this job for as long as he wants it, so it's not worth discussing that. Firing Boone might change something, but the real story here is that the Yankees consistently struggle to hit in October, and firing Boone won't fix that.
What sticks out on the table above is that their lone World Series appearance in the Boone era came in 2024. In the offseason prior to that season, Cashman swung a mega-trade for Juan Soto. Giving Aaron Judge a co-superstar did wonders, particularly when Soto did superstar things in October. Remember, his swing was the one that sent the Yankeess to the World Series.
Running it back with this group won't be enough. The Yankees' pitching staff is in great shape, but their lineup falters every October. The only year in which that wasn't the case was when the Yankees acquired Soto. Why not make that kind of move again?
It'll take that kind of blockbuster deal for Cashman to change the status quo and get the Yankees back where they should be in 2027. I don't know what that kind of deal would be in a bad free agency class, but with prospects like Dax Kilby and Carlos Lagrange, as well as a ton of starting pitching depth, the Yankees have the pieces necessary to acquire a star. It's on Cashman to get it done, once and for all.
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