Two Celtics-Bulls Trade Ideas That Make Sense

The Boston Celtics and Chicago Bulls have some trade chips that match up quite well.

Anfernee Simons, 26, fits better on Chicago’s timeline than Boston’s, and also, Simons and his explosive scoring might work against the Celtics’ tanking plans in 2025-26, if indeed it behooves Boston to lose consistently.

Will the Celtics purposefully tank this season? It’s difficult to imagine Brad Stevens or Joe Mazzulla endorsing anything resembling a tanking strategy. Even so, as Michael Pina of The Ringer recently noted, “Being bad makes a lot of sense for the Celtics. … It’s more than fair to believe that the Celtics are preparing to tank away this upcoming season.”

With Boston’s pseudo-tank on the mind, consider the following trade scenarios with the Bulls.

First of all, the Celtics could offer Simons to Chicago for center Nikola Vučević and a second-round pick.

Currently, the Celtics sit $1.9 million below the second apron after waiving JD Davison (per MassLive’s Brian Robb). A straight-up trade sending Simons to the Bulls for Vučević, both on expiring contracts, would create an additional $6.2 million in cap space for Boston. Vučević, a skilled but defensively challenged center, aligns with Boston’s potential tanking goals. His offensive prowess wouldn’t disrupt a losing effort due to his defensive shortcomings.

Given Simons’ youth and upside as a dynamic scorer, Boston could leverage Chicago’s eagerness to move Vučević and demand a 2028 second-round pick in the deal.

An even bolder Celtics-Bulls idea is possible after September 7, when Simons can be traded in multi-player packages by Boston. By including young forward Jordan Walsh with Simons, the Celtics could request Vučević and two second-round picks (2028, 2029) and generate a tad more cap space ($8.4 million) than they would in a Simons-Vučević swap.

Chicago, desperate to retool around younger talent, would likely jump at Simons’ potential. For Boston, acquiring Vučević would balance their depth chart while making them even more lottery-worthy.

Who says no?