Anfernee Simons landed with the Celtics as part of the Jrue Holiday trade with the Portland Trail Blazers, and everyone immediately speculated whether Simons would stay in Boston or not. Based on the latest update from NBA insider Jake Fischer, it sounds like the Celtics don't have a choice but to keep him on the roster.
Fischer said he didn't have any trade suitors to list for Simons, and that he isn't as optimistic as he originally was that the guard would be moved. Fischer noted that after Simons' contract expires at the end of this season (he'll make $27.7 million in 2025-26), he'll be due for a payday. Teams that may be interested in him have to consider that.
Fischer added that Boston's best chance to trade Simons will happen sometime during the season, if he makes a positive impact, showing the kind of player he is outside of Portland. The Celtics won't be the threat they were the past few years, but they should still make noise in the East.
The Portland-Boston trade was initially reported as Simons and two second-round picks going to the Celtics, but that changed after issues arose with Holiday's medical assessments. As a result, the Trail Blazers kept the picks, so it became a Holiday-Simons swap.
It looks like Anfernee Simons will start the season with the Celtics
Boston's motivation for trading Holiday was to get off the $100+ million that he's owed for the next three seasons. The Celtics' offseason plan shifted entirely after Jayson Tatum suffered a torn Achilles in the playoffs. He'll miss most, if not all, of next season.
Portland's motivation for acquiring Holiday wasn't as clear. Why would they want to commit that kind of money to a 35-year-old? The Trail Blazers needed an impactful veteran in the locker room, and Holiday fits that description (as does Damian Lillard). Trading Simons also frees up playing time for Portland's younger players, but then again, now they have Holiday to worry about.
The Celtics' attempt to trade Simons, but being unable to do so, makes the deal look better for the Trail Blazers, at least for the time being.
It took approximately three seconds after the trade was announced for the majority of people to declare that Boston won the trade. While that is and will probably remain true, at least Portland doesn't look as bad for trading Simons for Holiday.