The Boston Celtics made a bold trade to dump Jrue Holiday’s deal, but things keep getting worse as the franchise has been unable to move on from Anfernee Simons’ expiring contract. Boston wants to dip below the tax and reset the repeater penalties. This is a gap year with Jayson Tatum out. The Celtics would be wise to recalibrate their books and build a new contending roster when Tatum returns for the 2026-27 season.
This trade lowered their salary cap figure by $4.7 million and freed them from two full years of dollars. The Celtics saved even more when adding in tax penalties. This was a wise move, but Brad Stevens wasn’t done. He still has plans of flipping Simons to save even more. The Celtics are still $4 million over the first apron and $12 million above the tax line. Dumping Simons $27.6 million expiring deal before the deadline could allow Boston to dip under both figures.
The Celtics haven’t found a taker and might not. They don’t want to part with assets to move off his expiring contract, but teams just aren’t valuing score-first guards. This already looks bad, but it could become a nightmare as the trade deadline approaches.
Celtics regret trading for Anfernee Simons
Simons averaged 19.3 points, 4.8 assists, 2.7 rebounds, and 0.9 steals in 32.7 minutes per game last season. He is a plus shooter, but has struggled in his playoff opportunities. The 26-year-old is in his prime and looking for a massive contract. Teams just aren’t spending $30 million per season on a bucket-getter in the modern NBA.
This trade hasn’t gone to plan for either side. The Blazers signed Damian Lillard after his stunning buyout in Milwaukee. They now have two veteran guards serving as leaders for their young squad and may try to move on from Holiday quickly. That won’t be easy given the three seasons remaining on his contract.
Holiday is a two-time NBA champion capable of impacting winning on both ends of the floor. Some contender would have been interested before the deadline. That may not be the case with Simons. He will have to shine in the opening months for Boston to see the market improve.
This was not the Celtics' only salary dump. They have already traded Kristaps Porzingis and sent the primary return in the deal packing to save money. Boston was over the second apron last season and has already lessened their bill significantly. They want to do more, but it takes two to tango.
Anfernee Simons should thrive in head coach Joe Mazzulla’s system. Derrick White and Jaylen Brown provide defensive cover to hide mistakes. The Celtics still have hope that he can put up strong numbers and interest someone before the deadline. This will remain a problem until that trade happens.
The Boston Celtics have time to salvage it, but their biggest offseason move looks bad. Fans should have faith, but prepare for the worst. Cutting costs is always painful. Even with talented players, the Celtics are feeling that burden, and things will only intensify from here.