Jan. 22, 2026, 10:04 p.m. ET
The Boston Celtics have a tough decision to make ahead of the 2026 NBA trade deadline when it comes to whether they will retain the services of Anfernee Simons. The Celtics dealt for the former Portland Trail Blazers guard this offseason when they moved on from vet guard Jrue Holiday due to cap and perhaps age concerns.
The assumption at that time was that Simons was likely to be a short-timer with the Celtics given his large, expiring contract and seemingly ill fit with Boston to start the 2025-26 NBA regular season. But since then, the Longwood, Florida native has found his niche off the bench with the Celtics, even helping the team to win a few games. How to decide whether Boston should keep him or trade him? To that end, the hosts of “Havlicek Stole the Pod” linked up with “Third Apron” founder and cap guru Yossi Gozlan to host a mock trial on which way the Celtics could go with Simons at the deadline.
This was a fun and informative exercise for us, so be sure to tune in to hear how the trial played out (no one is in jail now, mind you, though there’s always a chance this could end with Boston in cap space prison).
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