The Boston Celtics have a frustrating habit of letting winnable playoff games slip through their fingers—and it’s a trend that’s been haunting the franchise since the early days of the Jayson Tatum and Jaylen Brown era. Now, as the 2026 NBA Eastern Conference Playoffs unfold, that old ghost has returned to haunt them in their first-round series against the Philadelphia 76ers. With two losses already on the board, the Celtics find themselves in a familiar, uncomfortable position.

So, what’s behind this recurring issue? Is it a lack of focus down the stretch? Poor execution in critical moments? Or simply the Sixers’ relentless pressure forcing Boston into bad habits? The answers aren’t easy, but the clock is ticking. The Celtics need to shake off these self-inflicted wounds fast—or risk watching the Sixers push this series to a decisive Game 7, or worse, steal it outright.

To break it all down, the team over at the “NESN” YouTube channel recently featured a segment from their “Boston Has Entered the Chat” show, with guest Dan Greenberg offering some sharp insights. They dive deep into what’s going wrong and whether Boston can turn things around before it’s too late. For Celtics fans, it’s a maddening déjà vu—but understanding the root cause might be the first step to fixing it.

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