The Boston Celtics entered the 2025-26 season with a clear financial goal: shed salary to drop below the first apron (and possibly the luxury tax) for maximum flexibility. Anfernee Simons—acquired in an offseason trade from Portland—has been the most frequently mentioned name in those discussions, with his $27 million salary this year making him a prime candidate to move.
Boston Celtics v Toronto Raptors
Despite the speculation, Simons hasn’t been dealt yet—with over a month until the February 5 deadline. The consensus? Boston would likely need to attach assets (draft picks or young players) to offload his contract, as his defensive limitations and expiring deal temper his standalone value.
Bill Simmons’ Proposal: Simons for Malik Monk (+ Salary Filler)
On a recent episode of The Bill Simmons Podcast, Simmons pitched an intriguing swap: Simons to the Sacramento Kings for Malik Monk, potentially with Doug McDermott added for salary matching (to keep Boston under the first apron).
Why it works for Boston:
Salary relief: Clears Simons’ $27M while adding Monk’s more manageable deal.On-court fit: Monk replicates much of Simons’ scoring punch off the bench—elite shooting (41.1% from three this season) and instant offense. His 2022-23 Sixth Man of the Year runner-up campaign (when Sacramento ended their playoff drought) proved he thrives as a spark plug for contenders.Efficiency boost: Monk’s numbers (11.8 PPG, 43.1% FG, 41.1% 3PT) provide similar microwave scoring without the defensive concerns.
Simmons’ logic: The Celtics replace Simons with a player who does “what he does” but in a winning context—perfect for a team already loaded with stars.
Why Sacramento Might Bite
The Kings are floundering (long playoff drought vibes despite adding DeMar DeRozan). Trading Monk for Simons could inject youth (Simons is 26 vs. Monk’s 27) and scoring upside, especially if Boston sweetens with second-round picks.
Sacramento’s “beam” remains mostly unlit—reassembling a mediocre core hasn’t worked. Simons could be a fresh start.
Reality Check
Boston would likely need to include picks or young assets to make it appealing.Monk’s bench role and efficiency make him a seamless fit, but Simons’ volume scoring might appeal more to a rebuilding Kings team.
With over a month left, this idea—or variations—could gain traction. The Celtics want cap relief without sacrificing contention. Monk checks those boxes.
Celtics fans: Simons-for-Monk keeps the offense humming while freeing money. Smart move or too sideways? Deadline drama incoming.