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Inside The Red Sox

Red Sox's Most Embarrassing Hidden Stat After Short Playoff Run

Here's how not-close the Red Sox have been to championship caliber
Sep 30, 2026; Bronx, New York, USA;  Boston Red Sox pitcher Garrett Crochet (35) is relieved in the sixth inning against the New York Yankees during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium.  Mandatory Credit: Vincent Carchietta-Imagn Images
Sep 30, 2026; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) is relieved in the sixth inning against the New York Yankees during game two of the Wildcard round for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images | IMAGN IMAGES via Reuters Connect

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As we continue to mourn the Boston Red Sox's extremely short playoff run this year, we have to examine the franchise's larger conundrum as it relates to winning a championship.

It's awfully tough to call yourself a contender if you're not close to running your division. And the current American League Division Series between the New York Yankees and Tampa Bay Rays is definitive evidence that the Red Sox are outclassed in the American League East.

But it's not just this season that the Red Sox are encountering this particular roadblock. We'd posit that the most embarrassing stat about Boston's recent shortcomings is the fact that in each of the last five seasons, at least two AL East teams have advanced deeper in the playoffs. In an era of unprecedented competence in this division, the Red Sox have been a mere afterthought.

Which teams have been better than Red Sox, and when?

Rays, Yankees
Oct 3, 2026; St. Petersburg, Florida, USA; New York Yankees catcher Austin Wells (28) is tagged out at third base by Tampa Bay Rays third baseman Junior Caminero (13) in the eighth inning in game one of the ALDS for the 2026 MLB Playoffs at Tropicana Field. Mandatory Credit: Pablo Robles-Imagn Images | IMAGN IMAGES via Reuters Connect

Here's the complete history of the Red Sox being overshadowed by deeper playoff runs from division rivals since they last made a deep run of their own in 2021:

2022: Red Sox finish last in AL East; Yankees, Blue Jays, Rays make postseason

2023: Red Sox finish last in AL East; Orioles, Rays, Blue Jays make postseason

2024: Red Sox finish third in AL East; Yankees, Orioles make postseason

2025: Red Sox lose in wild-card round; Yankees, Blue Jays advance to ALDS

2026: Red Sox lose in wild-card round; Yankees, Rays advance to ALDS

One has to imagine that it doesn't sit right as a player to sit on your couch after a season that might have been successful in a vacuum and still have to watch two division rivals duke it out in a deeper round of the playoffs. It's like you were a warm-up act to the real showdown.

So as the Yankees and Rays continue what looks to be a barnburner of a series this week, let's hope that everyone in the Red Sox organization is foaming at the mouth. It's not an easy offseason to maneuver with a lockout looming, but some drastic things need to be done to ensure this team looks like more of a contender whenever it hits the field again.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@moreviewsmedia.com