Hours before Anfernee Simons endured one of his roughest shooting nights in a Celtics uniform, news surfaced that Boston had already attempted to move the 26-year-old guard months ago.
Simons, who finished with just five points on 1-for-7 shooting from three in Tuesday’s 117–114 win over the Detroit Pistons, was the subject of multiple offseason trade conversations. According to Michael Scotto of HoopsHype, the Celtics explored several potential deals that would have sent Simons to a rebuilding team, including negotiations with the Brooklyn Nets.
Scotto reported that Boston and Brooklyn discussed “several trade scenarios” involving Simons that ultimately collapsed before the season began. The talks took place during a pivotal summer in which the Celtics maneuvered around the NBA’s second-apron restrictions while attempting to reshape their roster in the wake of Jayson Tatum’s season-ending Achilles injury.
Celtics Targeted Sharpe for Bigger Role
Getty Day’Ron Sharpe of the Brooklyn Nets looks for a pass around Luka Garza of the Boston Celtics.
The trade conversations were not centered on Simons alone. Scotto reported that Boston intended to pursue Nets center Day’Ron Sharpe in free agency, viewing him as a potential starter. Although the Celtics would have been limited to offering only a veteran minimum contract, sources told Scotto the franchise believed Sharpe could compete for the job.
Sharpe, currently backing up Nic Claxton in Brooklyn, is averaging modest numbers — 6.7 points, 5.5 rebounds and 1.8 minutes — in limited minutes. Boston’s interest is particularly notable amid its current shortage of frontcourt depth, especially after Neemias Queta suffered a left ankle sprain with no timetable for return. Sharpe’s size and rebounding ability would have addressed an area the Celtics have struggled to bolster all season.
Simons’ Expiring Deal Could Become Key Salary Lever
Boston remains $12 million over the luxury tax, but Scotto reported that the team is not under pressure to dump salary unless the right deal emerges. Simons’ contract, however, looms as a significant factor. He is in the final year of a $27.7 million deal, making him one of the Celtics’ clearest mechanisms to lower payroll if they choose to do so.
According to Scotto, the Celtics have resisted attaching a first-round pick to shed Simons’ contract, a stance that complicates their ability to create cap flexibility. The team could also dip below the tax threshold by moving shooter Sam Hauser and another minimum salary player, although Boston has not shown a willingness to break up its useful depth to achieve that outcome.
A Rocky Fit After Arriving as Boston’s Headline Addition
Simons was expected to play a major role after arriving four months ago as the centerpiece of Boston’s shaky offseason. He was fresh off a strong season in Portland, where he averaged 19.3 points in 70 games and shot above 42 percent from the field. With Tatum sidelined for the foreseeable future, Simons appeared positioned to take on part of the scoring burden.
Instead, he has been relegated to a bench role on a team hovering around the play-in standings. Through 18 games, he has averaged 13.9 points while coming off the bench in every appearance. His efficiency from long range — nearly 41 percent — has been a bright spot, but his inconsistency and contract status have made him one of the most discussed trade candidates linked to Boston this season.
A Trade Deadline Decision Looms Over Boston’s Future
Boston’s approach at the February trade deadline will reveal whether the franchise sees Simons as a temporary stopgap or a longer-term piece. With a roster still adjusting to life without Tatum, the Celtics must weigh whether Simons fits the timeline of a transition year — or whether moving him is the most strategic path forward.
Either way, his future with the Celtics now appears far from certain.
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