The Portland Trail Blazers pulled off one of the most surprising trades of the offseason, sending Anfernee Simons to the Celtics for Jrue Holiday. Portland also initially agreed to send two second-round picks to Boston, but the trade was later amended due to Holiday's medical records. It was a Simons-Holiday swap.
The Celtics trading Holiday wasn't surprising, not after Jayson Tatum ruptured his Achilles in the playoffs and changed Boston's trajectory. What nobody expected was for Portland to trade for Holiday (again). The Trail Blazers aren't contenders, so they seemingly traded for the 35-year-old for him to be a leader in a young locker room. It was an expensive move.
Even with that, the trade isn't a failure for the Trail Blazers, considering what the Celtics are going through with Simons. Boston has tried to trade him, but can't find a suitor to take on the $27.7 million he's owed in the final season of his contract.
There is uncertainty about how his scoring abilities will hold up on a good team. He came up short of averaging 20 points per game this past season (19.3), after averaging 21.1 points per game in 2022-23 and 22.6 points per game in 2023-24. Even if he thrives with the Celtics, it'll be expensive to extend him, giving Boston another reason to trade him before the season starts.
Celtics can't find a trade suitor for former Blazers guard Anfernee Simons
If a Simons trade doesn't materialize before the season starts, he could (and will most likely) be back on the trade market leading up to the February deadline. Teams that may be interested in him now might want to see how he fares in the first half of the season.
If his play is underwhelming, Boston will regret trading for him in the first place. A Holiday trade needed to happen, but the Celtics might already wish they had gotten a different player in return. This can't be the situation that Brad Stevens thought his organization would be in.
Say what you want about Portland trading for Holiday (and what you say is probably right), but at least it's not a trade that's aged well for Boston. Who knows, maybe when the dust is settled, the Trail Blazers will be declared the winners of the deal. Damian Lillard and Holiday leading Portland to the 2027 NBA Finals? Let's go!
In all seriousness, the Trail Blazers were smart to trade Simons when they did, even if it were later than it should've been.