The Yankees have a path to the World Series that looks pretty inviting on paper, but one old problem still hangs over Aaron Boone: his team has not knocked out a higher seed in the postseason during his tenure.
That’s the hurdle facing New York as it gets set for the American League Division Series against the Tampa Bay Rays. The Yankees have the kind of postseason rotation that can carry a deep run, and if they get past Tampa, the next stop would be the American League Championship Series against either the Cleveland Guardians or the Chicago White Sox. But before any of that matters, Boone has to beat a team that has been a thorn in the Yankees’ side since 2026 began.
The pattern under Boone has been clear. New York has handled lower-seeded opponents like the Guardians, the Minnesota Twins, and, in the last two years, the Boston Red Sox. The higher-seeded teams have been the ones that have ended their seasons.
Last year, the Blue Jays won the American League East and eliminated the Yankees, even though both teams finished with the same regular-season record. In the year before that, the Los Angeles Dodgers beat New York in the World Series.
The Yankees missed the postseason in 2023, but in 2022 the Astros knocked them out. In 2021, the only time a lower seed got them, it was Boston in the one-game Wild Card.
In 2020, the first-place Rays ended their run. In 2019, it was Houston again, and in 2018, the Red Sox closed the door.
If the Yankees are going to get back to the World Series, they’ll have to do something they have not yet managed under Boone. The past doesn’t decide this October, but it does sit there in the background.
And even if New York gets past Tampa, the job still won’t be finished. Beating a rival would be a big emotional step, but it wouldn’t automatically send the Yankees to the World Series. The lesson from local sports history is simple enough: one breakthrough doesn’t guarantee the next one.
Boone and his team have to keep that in mind. Getting rid of the Rays would matter. It just can’t be treated like the final word.
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