Coby White trade puts immediate Anfernee Simons Celtics reunion in play

If Brad Stevens pulls this off...
Jan 18, 2026; Chicago, Illinois, USA; Chicago Bulls guard Coby White (0) celebrates with forward Jalen Smith (25) against the Brooklyn Nets during the first half at United Center. Mandatory Credit: Patrick Gorski-Imagn Images
Jan 18, 2026; Chicago, Illinois, USA; Chicago Bulls guard Coby White (0) celebrates with forward Jalen Smith (25) against the Brooklyn Nets during the first half at United Center. Mandatory Credit: Patrick Gorski-Imagn Images | Patrick Gorski-Imagn Images

If an NBA team trades a player and that team waives him, the trading team is not allowed to sign that player. So, if the Bulls were to buy out Anfernee Simons after the trade deadline, the Celtics would not be able to pick him back up.

However, if a player were to be traded a second time, then bought out, the original trading team would then be able to sign that player as a free agent. In other words, if the Bulls flip Simons again before the Thursday deadline, and the team that acquires him buys him out, the Celtics would be able to sign Ant back to the roster.

This scenario may seem far-fetched, and it’s still a long shot, but the Bulls already had a glut of guards after adding Simons, plus Jaden Ivey and Mike Conley in a separate deal. Then, on Wednesday afternoon, they agreed to flip Conley and Coby White to the Hornets in exchange for Collin Sexton and Ousmane Dieng.

The Bulls are clearly blowing up their roster a bit, and they want to rebuild around their young players, Matas Buzelis, Josh Giddey, and whoever is left. They’re making moves to add assets smartly, and if an opportunity pops up for them to move Simons for some value in the next 24 hours, they won’t hesitate.

Celtics should welcome Simons back with open arms

If anything, the Bulls should be trying to make their team worse and get the best draft pick possible. That’s far from their M.O., so it remains to be seen if they’ll actually do it, but it would be in their best interest. If they can use Simons’ deal to bring in another 2nd round pick or something of that ilk, it’s a no-brainer.

That would open the door for Simons to be on the move before ever even arriving in Chicago. He would likely be used mostly as salary filler, and whatever team adds him may have no use for him and his expiring deal, especially if it’s a young team that’s not trying to compete.

So the idea of Simons hitting the open market isn’t that crazy, and the idea that the Celtics could bring him back shouldn’t be either. There has already been some reporting and speculation that Conley could be bought out by Charlotte and return to the Timberwolves in the exact hypothetical situation I’m describing with Simons.

Why not? This would be yet another stroke of brilliance by Brad Stevens if he’s able to bring Simons back for the stretch run, on a minimum deal. He was becoming a fan favorite and seemed to be a beloved teammate, and his scoring was very impactful off the bench. Trading him and a good 2nd round pick for Nikola Vucevic was a tough pill to swallow, but if he ends up back in Boston a week or so from now, that would be quite the coup from the Celtics.

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