The Trail Blazers traded for Jrue Holiday again this summer, intending to keep him in Portland this time. Meanwhile, the Celtics' motivation to trade for Anfernee Simons was primarily financial as they were able to get under the second apron this summer. That left many wondering whether Boston was Simons' final landing spot.
However, according to NBA insider Jake Fischer, signs point towards Simons wearing Celtics green to start the 2025-26 season.
"I really don't have any suitors to say for you guys right now, unfortunately. I'm not as optimistic about him getting moved prior to the year as I was with [Georges] Niang. Niang was on a much smaller number -- $8 million compared to Simons' $22 million," Fischer said. "Simons is someone who is still kind of on a career ascent, hopefully from his standpoint, who, on his expiring deal, is going to be looking for another big contract. He's going to be looking to play into another big contract. Any team looking to trade for him right now is going to be a team that has to be considering what his next deal will look like."
Blazers found a way to salvage Anfernee Simons' value
The Celtics will have difficulty finding anything of value for Simons. His archetype as an offensive-minded combo guard isn't coveted enough for teams to trade for him, knowing that they'll likely have to pay a premium to keep him around beyond next season.
You could argue that Blazers general manager Joe Cronin should've traded Simons sooner to maximize Portland's return. He was deemed a top ten trade asset by Bleacher Report's Zach Buckley just last summer, partly because he had two years remaining on his contract. But Fischer's update shows that the Blazers were right to take a 'better late than never' approach, ultimately deciding to move on from Simons.
It's debatable whether they won the actual trade, acquiring a 35-year-old Jrue Holiday set to make $104 million over the next three years. But in some ways, it was simply a swap of two overpaid guards, with Holiday being the better fit for Portland's defensive identity and win-now aspirations.
Holiday averaged just 11.1 points and 3.9 assists last season, but also battled injuries and had a diminished role on a stacked Celtics team. That said, it's concerning that Portland revised the trade to a straight one-for-one swap, removing two second-round picks due to Holiday's medicals.
It was time to move on from Simons, and the Blazers needed to get something rather than letting him walk in free agency next summer. Now, they need Holiday to produce enough to justify his contract. It's excellent that Portland received an asset for Simons, but it remains to be seen whether Holiday is a positive or negative asset at this point in his career.