One of the moves the Boston Celtics made in their successful quest to dip below the NBA's second apron saw them trade Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and a pair of second-round picks. Simons is a good player, but it's abundantly clear that the goal of the Holiday trade was to shed cap space. The fact that the Celtics are already reportedly considering shopping Simons, according to Jay King of The Athletic ($), only adds to that fact.
"Looking to continue shedding salary, the Celtics have explored the idea of flipping Simons’ $27.7 million expiring contract, according to league sources. In such a move, they would be aiming to accomplish two organizational directives Brad Stevens emphasized after the first round of the NBA Draft on Wednesday: regaining more roster flexibility and setting up a path to retain free agents Luke Kornet and Al Horford," King wrote.
The Celtics would like to re-sign veteran free agents Luke Kornet and Al Horford, but doing so while keeping their newly found flexibility would be challenging with their current roster as constructed. Parting with Simons' $27.7 million expiring contract would help accomplish that goal.
Celtics could look to shop Anfernee Simons before he plays in a game for Boston
It'd be a bit strange to see Simons get rerouted before even suiting up in a Celtics uniform, but it's hard to say that flipping him wouldn't make sense for a Celtics team that is clearly not all-in on winning now.
Simons, as mentioned above, is on an expiring contract. This essentially means that the Celtics would be wise to either commit to him as a major long-term piece on their team or flip him now to get something of value in return. Given Simons' deficiencies on the defensive side of the ball, it isn't shocking to see the Celtics considering going with the latter option.
Simons is a very talented offensive player, but he has been inefficient throughout his NBA career, isn't the best playmaker, and doesn't offer much defensive value. Given Boston's previous investment in Holiday, they prioritize defense at the point guard position.
Jayson Tatum's injury has Celtics in unfamiliar territory
After winning the 2023-24 NBA title, it was easy to expect Boston to be in the title hunt annually for a long time. Jayson Tatum's Achilles tear, which will likely cost him most, if not all, of the 2025-26 campaign, has them in unfamiliar territory. They're clearly setting up to compete in two years from now when Tatum is fully healthy.
With that in mind, saving some money, gaining some flexibility, and figuring out who will be alongside Tatum when he's ready to return makes sense. An aging and regressing veteran like Holiday and an oft-injured and expiring Porzingis were clearly not part of their future plans so they were traded. If the Celtics deem Simons isn't in those plans either, he will be gone too.
What they can expect in return, though, for only one guaranteed year of a talented Simons with very real flaws, though, remains to be seen.