It’s no secret the Boston Celtics are in a retooling phase amid looming financial constraints.
Boston has fallen out of title-contender status after Jayson Tatum’s torn Achilles, which he sustained in the Eastern Conference semifinals. The superstar is expected to miss most, if not all, of the 2025-26 campaign due to the injury. In the aftermath of Tatum’s injury, the Celtics traded Jrue Holiday and Kristaps Porzingis in cost-cutting moves. Now, rumors have swirled about the team rerouting Anfernee Simons after acquiring him in the Holiday deal.
The Celtics’ offseason has been defined by salary-shedding maneuvers, and it wouldn’t be shocking if that trend continues into the regular season.
Simons trade proposal lands Boston wing depth
Andy Bailey of Bleacher Report recently compiled a three-team trade that would reroute Simons and save Boston cap space.
MORE: Sixth Man of the Year named Celtics’ biggest riser ahead of 2025-26 season
Here’s Bailey’s proposed trade:
Celtics receive: Ochai Agbaji, Terance Mann, 2030 second-round pick (TOR)
Raptors receive: Anfernee Simons
Nets receive: RJ Barrett, 2031 second-round pick (BOS)
In this scenario, the Celtics would acquire Agbaji, a former No. 14 overall pick and promising 25-year-old forward who is coming off a career-best season with Toronto. Agbaji posted several career highs last season, during which he averaged 10.4 points, 3.8 rebounds, 1.5 assists and 0.9 steals across 27.2 minutes per game in 64 regular-season appearances.
With the Raptors’ solid depth on the wing, it would make sense for them to move the Kansas product. He’s also set to enter restricted free agency in 2026-27, so the Celtics wouldn’t be tied to a long-term financial commitment. Toronto has Scottie Barnes and Brandon Ingram on the roster, so the team can also afford to lose Barrett.
Boston would also add Mann in this proposed deal, who was traded to Brooklyn in June. Mann would help shoulder the wing load while Tatum is sidelined. Mann is under contract through 2027-28 and could remain a useful depth piece in the years ahead.
Simons doesn’t appear to be part of Boston’s long-term plans, so trading him before he reaches free agency could be a practical move for a franchise in transition.
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