Anfernee Simons was an obvious trade candidate for Portland this past offseason, but the expectation was that the rebuilding Trail Blazers would move Simons in exchange for future assets. General manager Joe Cronin took the opposite approach, swapping Simons for a 35-year-old Jrue Holiday with the Boston Celtics.
That shocking and aggressive move received criticism from the start. Question marks surrounded Holiday's fit with Portland's timeline and his $104 million owed over the next three seasons, which many deemed to be an overpay due to his declining play in Boston.
But it took less than ten games with the Blazers for Holiday to shift the narrative. Holiday is averaging 17.4 points, 7.6 assists, 4.9 rebounds, and 1.4 steals on 46/37/82 shooting splits, which are statistically similar to his three-year stint with the Milwaukee Bucks. He's a proven winner who is already changing the entire culture in Portland for the better.
Blazers already the big winners of blockbuster Jrue Holiday trade
Holiday may have lost a step athletically, but he still has plenty of gas left in the tank to be incredibly impactful on both ends of the court. He's a perfect fit for what the Blazers were hoping to accomplish this season with their defensive-minded approach.
Even better, his value goes far beyond the improved statistics, providing Portland with a much-needed leader in the locker room. The situation surrounding Chauncey Billups could've easily derailed the Blazers' momentum they were hoping to carry over from the strong finish to the 2024-25 season, especially given how young this roster is. But thanks to Holiday, that has just become a footnote in their season.
Meanwhile, Anfernee Simons' time in Boston hasn't gone according to plan.
As expected, he's still shooting well from beyond the arc at 37.9%, but his overall scoring (14.3 points per game) and playmaking (1.6 assists) have taken a drastic dip. In Boston's most recent loss to the Orlando Magic, Simons played just 18 minutes!
The Celtics didn't make this trade because they thought Simons was a better player than Holiday. They did it because they essentially had to as a team that needed to duck the second apron, especially with Jayson Tatum, unfortunately, set to miss a significant portion of the season after suffering a torn Achilles. Credit Cronin and the Blazers for capitalizing on the Celtics' financial crunch.
It was a surprising trade considering Portland was the team that initially traded Holiday to Boston after acquiring him from Milwaukee as part of the blockbuster Damian Lillard trade. Thanks to this full-circle moment, everything ultimately worked out in Portland's favor. By swapping Simons for Holiday, they were able to upgrade in several key areas, landing not only a better player but also a better fit for their system.
With the two guards trending in opposite directions to start the season, it's already become apparent that Portland fleeced Boston in this once-polarizing deal.