NBA Rumors: Ranking 10 riskiest and most questionable offseason moves

1. Boston Celtics signing Jaylen Brown to supermax extension

Heading into the offseason, the writing was on the wall. The Boston Celtics were likely going to sign Jaylen Brown to a supermax extension. While it may have taken a while to get to that point, that’s exactly what happened. The Celtics officially agreed to a five-year, $304 million extension with Brown. With this move, the Celtics have essentially said that this is the core that they’re either going to win a championship with or one that they’re going to fail with.

The future is now (or has to be now) for the Celtics. The big question is whether the duo of Brown and Tatum or the trio of Kristaps Porzingins, Brown, and Tatum will lead this team to a championship. There’s no guarantee of that but it’s going to be increasingly difficult for the Celtics to ever trade this Brown contract, even if he plays to his potential.

On the other hand, what alternative did the Celtics really have? Should they have traded him? Eh. Should they have not paid him to risk creating an unnecessary issue between the two sides? No. This is a move that the Celtics probably had to do.

That said, that doesn’t mean it’s not risky and one that could end up being one of the bigger missteps from this offseason.