Yankees Must Break Postseason Trend That Has Haunted Aaron Boone

One thing has plagued Aaron Boone since he was hired as manager of the New York Yankees in 2018.

New York Yankees manager Aaron Boone (17) walks back to the dugout after making a pitching change during the third inning against the Baltimore Orioles at Yankee Stadium. | IMAGN IMAGES via Reuters Connect

The New York Yankees are more than equipped to make a World Series run and potentially win their first championship since 2009. The Tampa Bay Rays stand in their way in the American League Division Series, and the inevitable bout has been brewing since the season started, with Tampa clearly a thorn in New York's side since 2026 began.

With the best rotation in the postseason, it wouldn't surprise anyone if they usurped the Rays and headed to the American League Championship Series, where they would face either the Cleveland Guardians or the Chicago White Sox. Still, one thing stands in manager Aaron Boone's way. It's a trend he hasn't bucked during his tenure as manager. That's beating a higher seed than him in the postseason.

The Yankees have had an easy time if they're facing the Guardians, Minnesota Twins, or, in the last two years, the Boston Red Sox. These higher-seeded teams have been the bugaboo, though. Last year it was the Blue Jays, who won the American League East, despite tying the Yankees' record in the regular season. The year before that, the Los Angeles Dodgers beat them in the World Series.

Los Angeles Dodgers first baseman Freddie Freeman (5) accepts the Willie Mays World Series Most Valuable Player trophy after winning the 2024 MLB World Series against the New York Yankees at Yankee Stadium. | USA TODAY Sports via Reuters Connect

The Yankees weren't in the postseason in 2023, but in 2022, the Astros sent them home. 2021 was the only time a lower seed sent them home. That was the one-game Wild Card against Boston. In 2020, the first-place Rays sent them home. In 2019, the Astros sent them home, and then in 2018, the Red Sox ended their season.

Ending the trend doesn't guarentee anything

If the Yankees are going to make it back to the World Series, they'll have to do something they have never been able to do. Every year is different, and last year's postseason follies don't predict what will happen this year, but it still hangs over Boone's head.

Of course, just beating the Rays doesn't guarantee they'll even head to the World Series, even if a Central team is waiting for them. If local sports history has taught us anything, those New England Patriots were in the New York Jets way for years, and even though they finally beat them in the Divisional round back in 2011, Rex Ryan's group was unceremoniously sent home the next week by the Pittsburgh Steelers.

New England Patriots head coach Bill Belichick greets New York Jets head coach Rex Ryan after the game at Gillette Stadium. The Patriots defeated the Jets 30-21. | IMAGN IMAGES via Reuters Connect

Boone and the rest of his squad need to avoid that. Sending home a bitter rival would be an emotional win, but it isn't the end of the line if they do.