No team hurt itself more this offseason than the Boston Celtics. Not the team with the goofiest contract. Not the team that sat on its hands. Boston managed to combine the worst of both worlds at the exact moment it could least afford to.
Start with the report card. When NBC Sports handed out 2026 free agency grades, the Lakers and 76ers earned an "A." The Celtics? The headline said they "may need to retake class." When your division and conference rivals are getting gold stars and you're getting a note sent home to your parents, that's not a vibe. That's a warning sign.
Now layer in the context that makes this sting. Boston is coming off Jayson Tatum's Achilles rupture, the injury he's been grinding back from, returning to the court roughly four months after the tear during the 2025-26 season and even taking his comeback on the road. That's a franchise that needed a bridge summer: stabilize, add shooting, keep the core intact and let your best player heal. Instead, reporting through mid-July 2026 has Boston taking on Paul George's contract, the four-year, $212 million max he signed with Philadelphia back in 2024, in a reported move connected to shipping out Jaylen Brown.
In a year built around patience, the reported path was to absorb an aging max deal and part with a proven star wing. If you're picking your poison this offseason between a bad contract, a botched trade, or standing pat, Boston reportedly ordered all three off the menu.
Compare that to the summer's other punchlines. Yes, Milwaukee earned the "worst signing" crown: Sports Illustrated flat-out called the Gary Trent Jr. contract "bizarre" and put it atop its list of the offseason's worst deals. That's an embarrassing line item. But it's one line item. A single odd signing doesn't sink a season the way reshaping your roster around a max contract while a rival stacks an "A" summer does.
That's the real dagger here. Self-harm in the NBA isn't absolute, it's relative. You don't get worse in a vacuum, you get worse because the guy across the standings got better. The Lakers got an "A." The Sixers got an "A." The Celtics got told to come back next semester. Even if every individual Boston move can be defended on its own, the scoreboard that matters reads: your rivals up, you down.
So here's the call, and I'll stand on it: Milwaukee made the funniest mistake, but Boston made the costliest one. A weird contract you can bury on the bench. A questionable direction with a healing franchise player while rivals pass you by? That echoes into the spring.
Prove me wrong, Boston. As of mid-July, you haven't.