The Portland Trail Blazers swapped Anfernee Simons for Jrue Holiday with the Boston Celtics this offseason. Early returns suggest that the surprising decision is a significant win for Portland, given how the two guards have played for their respective teams this season.
Holiday has been sidelined with a right calf strain as of late, but has been incredibly impactful for the Blazers when healthy, and appears to be in the midst of a resurgent season in Portland after a relative down year in Boston.
Simons, meanwhile, is trending in the complete opposite direction with his new team. The Celtics guard appears to be struggling in his new sixth man role, averaging 13.4 points, 2.5 assists, and 2.3 rebounds on 44/40/87 shooting splits.
Anfernee Simons' struggles prove Blazers right to trade him
His floor spacing ability is still there, with Boston even using him more off-ball than he was able to play in Portland. But the trade-off is that Simons' combo guard skill set isn't fully utilized in his playmaking.
Simons doesn't quite fit head coach Joe Mazzulla's preferred style of play, which, combined with a crowded backcourt that includes Derrick White and Oregonian Payton Pritchard, leaves him in a limited offensive role as a microwave scorer off the bench. That can still be valuable, as the Jayson Tatum-less Celtics surprisingly sit third in the Eastern Conference with a 15-9 record.
That raises the critical question of whether a contender can have Simons on their roster.
Boston is using him correctly in that sixth-man, microwave scorer role. At the same time, they're also not fully utilizing his skillet, as Simons has averaged just 23.6 minutes per game with a 23% usage rate. Given his limitations as a two-way player, Simons is best suited for this role on a contender, but the issue is that he's not paid to be that level of role player. He's on an expiring $27.7 million deal.
The Blazers front office realized this and proactively got ahead of the contract dilemma, securing a better, more long-term option in Holiday (who is still objectively overpaid, but still an upgrade).
We've seen how vital Holiday has been for the Blazers with their recent struggles in his absence. He's been sidelined since the Blazers' Nov. 14 loss to the Houston Rockets, and Portland has dropped nine of its last 12 games during that stretch.
Boston wouldn't miss Simons to that extent, and is actually actively looking to shop him before February's trade deadline.
It remains to be seen if they'll find value for him, given these limitations and expiring deal. Two previously mentioned landing spots were the Brooklyn Nets and Milwaukee Bucks, although the latter is now heavily dependent on the situation surrounding Giannis Antetokounmpo.
Still, the fact that the Celtics, a championship organization, already wants to trade Simons tells you all you need to know about his true fit on a contender. The Blazers made this swap to upgrade their roster, while the Celtics made it for financial reasons. It may still be a win-win given their respective situations, as both teams got what they were hoping to achieve from the shocking deal.