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The Celtics Said ‘Why Not Both?’ and Their Postseason Stung Way Harder Than Expected

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

Man, talk about a ride. The 2025-26 Boston Celtics season was a total head-scratcher, swinging from a “shockingly positive” regular season to a “surprisingly negative” postseason, proving that even the most grounded predictions can get completely flipped on their head. Seriously, who saw that coming after how well they played for months?

That “Gap Year” Prediction? Yeah, Right.

Before the season even kicked off, the talk around the Celtics was all over the place. Pundits were throwing out everything from a “deep postseason run” to a full-blown “tanking season” where half the starting lineup would get shelved. The whole vibe was that 2025-26 was just a “gap year,” a development season to figure out which pieces fit for 2026-27 and beyond. The idea was to focus on the future, almost at the expense of wins and losses. Sounds like a cop-out, right?

But Joe Mazzulla, Jaylen Brown, and the rest of the team apparently got a different memo. They looked at that “gap year” tag and basically asked, “why not both?” Instead of just developing, they went out and had a “shockingly positive” regular season while still getting those young guys some serious run. Actions definitely spoke louder than any words or predictions, turning what many saw as a placeholder season into a legitimate statement about their immediate intentions.

Simons Was Gone, But The Youth Shined

A huge storyline early in the season was the arrival of Anfernee Simons, who came over in the Jrue Holiday deal. Everyone knew he was a super talented scorer, and he was set for a big role, but the dude was also a free agent at the end of the year and a prime trade candidate. Talk about writing on the wall, right? Turns out, that prediction was spot on. Fans got all hyped about keeping Simons around long term, only for Stevens to deal him at the deadline. Just like that.

But even with Simons’ quick exit, this Celtics squad had a really youthful look to it. That kind of roster can bring higher variance in outcomes, for sure, but it also opened the door for a deeper bench. We saw some intriguing talents and skillsets emerge, with players like Minott and González providing some serious wing athleticism. That depth was a big reason why the regular season had so many positive vibes swirling around.

So, here we are in September 2026, looking back at a season that delivered wildly different experiences. The Celtics defied expectations by crushing the regular season, showcasing that development doesn’t have to come at the expense of winning. But then that “surprisingly negative” postseason hit, leaving everyone wondering what happened when it really mattered. The biggest question for the 2026-27 season has to be how they bottle that regular season magic and make sure it translates when the stakes are highest.

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

Originally reported by Celtics Blog.

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