Wow, did not see this one coming. The question is why does Portland want Holiday? I think the reason is that Holiday has more value than Simons. Not necessarily to Portland, but Holiday has more trade value than Simons overall. The Celtics were so hamstrung due to the second apron that it was hard for them to trade Holiday. Portland will have a lot more flexibility to make something work. We'll see.
As to Simons, maybe for the Celtics, it is easier to move an expiring contract for something. I don't know. I have been saying all along that I think BOS is targeting 2026-27 to get back on track for salaries. Or maybe there is a team that will be more willing to take on Simons in a salary dump trade.
I think this will work out for Portland. I expect them to flip Holiday for some decent value. More value than they could have gotten in a straight trade for Simons. For BOS, this seems more about 2026 than 2025.