The Portland Trail Blazers shipped Anfernee Simons in exchange for Jrue Holiday roughly two months ago. Although neither player has officially played for their respective new teams, much about the dynamic surrounding the trade has since shifted.
The Boston Celtics have struggled to flip Simons as teams around the league are concerned about his expiring contract and what that means for their long-term plans should they acquire the skilled but likely overpaid combo guard. Boston now has to decide whether to bring Simons off the bench, which is a similar situation to the one Portland faces with Holiday.
Still, there are key differences behind their reasoning for this deal, making it seem more beneficial from the Blazers' standpoint.
The Jrue Holiday-Anfernee Simons swap is tilting in Portland's favor
The Celtics wanted to duck the second apron and moved Holiday for a cheaper expiring contract in Simons. But Simons' overall fit on their roster is questionable, despite the obvious three-point shooting alignment, as the Celtics attempted the most threes per game last season by a wide margin. Following the departure of Kristaps Porzingis and, inevitably, Al Horford, Boston desperately needs more help in the frontcourt. Ideally, Simons would be the perfect trade candidate to balance out their roster better, but that doesn't appear to be gaining any traction.
Both teams are facing their own dilemmas as a result of this trade, but Portland's was by choice.
They want to be in this situation, having Holiday help achieve their win-now goals while also improving their long-term outlook by providing valuable mentorship to their young backcourt. Boston didn't want to take on Simons; they essentially had to -- if it weren't Simons, it would have to be someone else. It's too early to declare a winner definitively, but that key difference alone makes this trade shape up to be in Portland's favor.
Say what you will about the $104 million, three years remaining in Holiday's deal, but Simons is likely going to command close to that annually as well. Both guards are overpaid in the scheme of things under the new CBA, but which one is overpaid for the right reasons?
Boston is winging it with the situation surrounding Simons, trying to use him as a stepping stone to greener pastures that no team is offering them. Meanwhile, Portland acquired Holiday to help achieve clear-cut roster goals, rather than viewing this as a financial opportunity that they had no choice but to take.
The Blazers also bought low on Holiday after a down year in which he was limited by injury and averaged 11.1 points and 3.9 assists. Although he's 35 years old, there's a possibility that Holiday's stock will increase in Portland as he gets healthier and takes on an expanded offensive role.
Judging by the fact that Simons remains in Boston, we can assume there's little value around the league for him. Meanwhile, Portland could build up Holiday's value and potentially flip him to a contender at the deadline.
We'll have to see how this all plays out, but two months in, the trade is looking increasingly better for Portland.