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New York’s Playoff Failures Are Absolutely Stealing Aaron Judge’s Ring Chances, And It’s A Cruel Joke

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Houston Astros logo on gradient background — Created by the Sports On Tap desk | Source : Sports On Tap (team logos property of their respective owners)

Aaron Judge, at 34 years old, isn’t even healthy enough to be on the field right now, and his Yankees are staring down another brutal early playoff exit. They’re trailing the Rays in the ALDS in 2026, on the brink of another postseason loss in the Judge era. Honestly, it’s just criminal how this organization keeps coming up short despite having one of the game’s best sluggers. They’ve had one World Series appearance and three ALCS berths with him, but it just hasn’t been enough.

The “So Close Yet So Far” Early Years Were Just a Preview

Think back to 2017. Judge’s rookie year, dude absolutely mashed 52 homers, dragging them to a wild-card spot. You thought, “Okay, this is the start of something big, right?” They took down the Twins in the Wild Card Game, then Cleveland in the ALDS. They even pushed the Astros to the absolute limit in the ALCS, taking a 3-2 series lead. Three straight wins! But then Justin Verlander shut them down in Game 6, and Houston dropped a 4-0 goose egg on them in Game 7. One win away from the World Series, and boom, season over. Just brutal.

Then 2018 rolls around. They won 100 regular season games, 100! But they were still a wild-card team. Judge was part of a lineup that had six dudes hitting 20-plus homers. They beat the A’s in a one-game Wild Card battle, but then Aaron Boone’s first season at the helm ended quickly. The eventual champion Red Sox absolutely stomped them in the ALDS in four games, including a ridiculous 16-1 beatdown in Game 3. You just can’t be winning 100 games and get bounced like that.

The Altuve and Brosseau Heartbreaks Showed a Pattern

By 2019, you figured it had to be their year. They won the AL East for the first time with Judge, putting up a monster 103 wins. They looked unstoppable, sweeping the Twins in the ALDS. But then, it was the Astros again in the ALCS, just twisting the knife. Jose Altuve, Gerrit Cole, Alex Bregman,that era of Astros always seemed to have their number. Houston took the series in six games, capped by Altuve’s walk-off homer off Aroldis Chapman in Game 6 to send them to the World Series. You could just feel the air go out of the city with that one.

Even the weird, shortened 2020 season couldn’t save them. They grabbed another wild-card spot, winning 33 of 60 games. Same story, though: a Wild Card sweep over Cleveland, and then an ALDS loss, this time to the Rays. In the deciding Game 5, Judge actually hit a homer, but that was their *only* run. Chapman coughed up a homer to Mike Brosseau in the eighth, and that was it. Another season, another gut-punch exit.

Fast forward to now, 2026. Judge is 34, not playing, and the Yankees are right back in that familiar spot, trailing in the ALDS. It’s a tragic tale for one of baseball’s biggest stars, and it’s hard to watch his prime just… slip away because the team around him can’t close it out. If they can’t turn this series around against the Rays, it’s going to be another long winter wondering what could have been for Judge.

This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.

Originally reported by The Sporting News.

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