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Brad Stevens starts offseason by trading for optionality

June 24, 2025 by Celtics Blog

The Celtics now turn to Brad Stevens to help navigate an offseason filled with uncertainty
Photo by Suzanne Kreiter/The Boston Globe via Getty Images

The Boston Celtics have a lot of work to do this offseason so Brad Stevens is maximizing his flexibility

Well that didn’t take long. The Celtics kicked off the offseason by trading a guy everyone knew could be traded to a team that nobody had pegged for his next destination.

Jrue Holiday will always be remembered as a key contributor to the 2024 Championship and a heck of a human being. But he makes a lot of money and that wasn’t going to be a great long term fit with the 2nd apron restrictions.

Despite playing a similar position, Anfernee Simons is nothing like Jrue Holiday. He’s a more dynamic offensive player who …struggles on the defensive end. They both shoot well from 3 (at least in most years) but Simons shoots a higher volume. Holiday is a veteran leader most likely with his best years behind him while Simons is only 26 years old and entering his prime years.

This move, at face value, shifts the Celtics focus a bit from defense to offense. Perhaps the idea is to sprinkle in a little more of the Indiana style of pace and scoring optionality. There still has to be a plan to provide a defensive gameplan and roster that can hold up deep into the playoffs. It isn’t like White, Brown, and others will forget to play defense, but you can only cover up for so many weak links.

All of which makes me think that this is just the first chess move of Brad Stevens’ offseason strategy. Simons, at this moment, is an expiring contract, so the Celtics have options with him. If he works out as a perfect fit and the team can cut enough costs elsewhere, there’s a chance he gets re-signed to a long term deal. If the team needs to shed a lot more salary next year, they can just let him walk as a free agent. Perhaps more likely, they can shop him either this summer or at the trade deadline to a team that needs more scoring (Orlando would have been a potential spot before the Bane trade).

Remember that this trade doesn’t exist in a vacuum. You can grade it out and decide who “won” or “lost” the deal. But it all depends on what the next moves are for the Celtics. Is Porzingis the next shoe to drop? What’s the return for him? Does Hauser exit stage left as well? Who are the Celtics drafting?

If they keep him, Simons does fit the Celtics new timeline. He can help Jaylen Brown carry the offensive load next season. If re-signed, he’d still be 27 the following year and ready to fit in next to Tatum and Brown.

It is just too early to know what this team is going to look like going forward. I could hit publish on this post and the next deal could happen within moments. We’re a day away from the NBA Draft, where a lot of trades occur.

The bottom line is, however, that Brad Stevens just gave himself more options. Not a bad piece of work to start things off.

Filed Under: Celtics

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