There were two camps when it came to Anfernee Simons’ role with the Blazers: those who felt he was key to Portland’s recent success and should be valued as such, and those who felt he was holding Portland back and should be moved regardless of the cost.
Given the news of Simons being shipped out to Boston for Jrue Holiday, both camps seemingly lost in this trade.
Replacing Simons with Holiday makes Portland better at what it was good at (defense) and worse at what it was bad at (offense). While he was traded for a player who is currently better than him overall, it puts even more pressure on Portland’s young projects to score efficiently and immediately.
Moving Simons does pave the way for Scoot Henderson and Shaedon Sharpe to take control of the backcourt, but adding another point guard doesn’t give them the clear runway many fans wanted. Holiday should, in theory, be more willing to make way for an ascending young player and transition to a bench role compared to Simons, but the overall logjam still remains.
Defensive Identity
Portland clearly is leaning into its defensive identity with this trade. A rotation that includes Deni Avdija, Toumani Camara, Jrue Holiday, Matisse Thybulle and Jerami Grant, who was an amazing defender in the middle of last season before he was sat, with Clingan waiting in the wake to protect the rim, is daunting.
The Blazers had the fourth-best defense in the league after the All-Star break and were even better dating back to the exact midpoint of last season. They trade their arguably worst defender into an arguably still top-10 one, or an inarguable top-25 one. The Celtics were 3.4 defensive rating points better with Holiday on the court last season.
Simons and Sharpe were never going to be able to share the court long-term, and that was the starting lineup Portland would have been forced to run if Anfernee returned next year, especially if they extended him. The two of them were one of, if not the worst, defensive backcourts in the league. The Blazers were in the 20th percentile defensively when the two of them were on the court together.
Holiday’s Intangibles
The best part about Holiday coming to Portland might be his ability to mentor Scoot. If Scoot wants to be a long-time, winning player in this league, he’s going to have to turn himself into a presence defensively, something that is entirely possible.
Holiday and Henderson are very similar in stature, and Scoot has the willingness to learn and be active on that side of the ball. If Scoot develops into a Holiday-type player, possibly sacrificing a bit of defensive ceiling for increased passing prowess, that would be a great outcome for both the Blazers and Henderson.
The biggest issue with this trade is age, which has been a massive talking point among fans during this rebuild.
Portland is already dealing with the trials and tribulations of an aging Jerami Grant, whose performance wavered before eventually cratering, leading to yet another unfinished season for the wing. Grant is 31 years old. Jrue Holiday is 35 (as of two weeks ago). The Blazers are now even more openly committed to winning in a stacked Western Conference, something they’ve said many times.
If Holiday has begun his decline as a player, and/or doesn’t find it within himself to give it his all for his new franchise, then this deal will be scrutinized much more so than it already has been.
It’s Go Time
So now, as was the wish of almost all NBA fans, particularly a collective in Portland, the ceiling of this team is fully dependent on Shaedon and Scoot.
If Shaedon can become a consistent scoring threat, and more importantly, an efficient one, this trade will have benefited Portland. If Scoot plays well enough that at any point in the next three years he supersedes Jrue, then Portland will be just fine.
The contract isn’t as big of an issue as people make it out to be. Portland only took on an extra $5 million this upcoming year. They historically haven’t been players in free agency, so no worries there. They still have roughly $60 million in expiring contracts going into 2026-27, which will make way for Shaedon and Scoot, if they prove worthy of extensions.
Sentiment was growing that Portland would extend Simons, as opposed to sending him out in a trade for scraps. If they had done that, Portland would be in the same exact spot financially, or in an even worse one.
Reports have also shown that Portland intends to keep Holiday, so rerouting the veteran to another team is off the table.
In a vacuum, Jrue Holiday is a player who contributes to winning basketball more than Anfernee Simons does right now. However long that remains the case will ultimately determine whether this was a good trade for the Blazers.
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