Could Anfernee Simons Find His Way Back to Boston? Here’s How It Could Happen
The NBA trade deadline is always a whirlwind of roster reshuffling, and this year is no different. One of the more intriguing situations developing involves Anfernee Simons, the Bulls, and a potential reunion with the Celtics - but it’s going to take some maneuvering to make it happen.
Here’s the key wrinkle: under league rules, if a team trades a player and that player is then waived by the team acquiring him, the original team can’t re-sign him. So in Simons’ case, since Boston traded him to Chicago, if the Bulls were to buy him out after the deadline, the Celtics would be out of luck.
But there’s a loophole - and it’s a big one.
If Simons is traded again before the deadline, and then that next team decides to buy him out, the Celtics would be free to sign him as a free agent. It’s a bit of a maze, but it’s legal. And given how active Chicago has been leading up to Thursday’s deadline, it’s not entirely out of the question.
Bulls Are Reshaping Their Roster - Fast
Chicago has already been busy. After acquiring Simons, Jaden Ivey, and Mike Conley in separate deals, they turned around and flipped Conley and Coby White to the Hornets for Collin Sexton and Ousmane Dieng. That’s a lot of guards moving in and out, and it signals a clear direction: the Bulls are restructuring around youth.
They’re shifting focus to young core pieces like Matas Buzelis and Josh Giddey, and they’re clearly not done yet. With the deadline looming, Simons could be on the move again - not because he doesn’t have value, but because his contract could be useful in facilitating another trade. If Chicago sees an opportunity to add a future asset - even a second-rounder - by moving Simons, they’re likely to take it.
And if the team that acquires him doesn’t see him as part of their long-term plans? A buyout becomes a real possibility.
What This Means for Boston
If that domino falls - Simons gets traded again, then bought out - Boston would be in position to bring him back. And that would be a savvy move.
Simons had started to carve out a real role with the Celtics. His scoring punch off the bench was a valuable asset, and by all accounts, he was well-liked in the locker room.
Trading him - along with a solid second-round pick - for Nikola Vucevic was a tough but understandable move in the short term. But if Boston ends up with both Vucevic and Simons back in the fold?
That’s the kind of roster-building magic that wins Executive of the Year awards.
It’s not just wishful thinking either. We’ve seen similar situations play out before.
There’s already buzz that Mike Conley could be bought out by Charlotte and return to Minnesota under the exact same kind of scenario. So this isn’t some outlandish hypothetical - it’s a real possibility, especially in a deadline week that’s already been full of surprises.
The Bottom Line
The Bulls are clearly pivoting toward a youth-focused rebuild, and that means they’re not done dealing. Simons, with his expiring contract and scoring upside, could be a valuable trade chip in the next 24 hours. If he’s moved again and bought out, Boston could swoop in and bring him back for the stretch run - likely on a minimum deal.
It would be a smart, low-risk move for a Celtics team that’s already in win-now mode. Simons knows the system, fits the culture, and gives them another weapon off the bench. And for a team with championship aspirations, those little moves can make a big difference come playoff time.
So don’t rule it out. The path is narrow, but it’s there. And if Brad Stevens finds a way to walk it, it could be yet another masterstroke in a season where Boston is going all in.