If the Portland Trail Blazers weren't going to become buyers at the trade deadline, they should've flipped their approach to become sellers. The last thing they want to do is be in this purgatory as a team that misses the postseason with nothing to show for it other than another late lottery pick.
To make matters worse, the Blazers are overpaying veterans while still on track to fall short of the postseason. The most notable example is their win-now trade for Jrue Holiday, which was a polarizing decision at the time.
Portland's front office essentially doubled down on this decision at the deadline, as they could've flipped Holiday for a second time. But this time around, it looks like he's here to stay. And that's not a good thing.
Jrue Holiday could quickly become a negative asset for Portland
Holiday has a proven track record of elevating teams wherever he goes, proving to be the missing piece in both Milwaukee and Boston. But those are entirely different situations compared to the one he entered in Portland. The Blazers are simply looking to end a four-year playoff drought, and paying a hefty price for Holiday to be that missing piece.
It would be one thing if a contender were willing to look past Holiday's contract because they have limited roster flexibility and want to upgrade their roster for a better chance at a ring. That's really the only scenario that justifies taking on his massive $32.4 million contract.
Portland should've tried to find a team in that situation, whether it was the New York Knicks or someone else entirely, and sent Holiday there.
He's showing legitimate signs of decline, particularly as of late. That problem is only going to get worse as the gap between production and contract widens. The Blazers have lost six consecutive games and remain four games out of the 8th seed. The fact that they're not even in the playoff picture despite willingly taking on Holiday's contract proves this was a mistake, as the risk is far greater than the reward.
Holiday is on the books through a player option 2027-28, at which point he'll make $37.2 million at 37 years old. The last thing the Blazers want is to be stuck with that contract right when their young core is finally ready to make a playoff push. It would become a significant roadblock both in terms of retaining their youth and finding upgrades that move the needle more than Holiday.
This deadline presented a window for Portland to mitigate that risk by turning Holiday into whatever future assets they could, ideally attached with a salary filler on a more short-term deal. But the Blazers have decided they like where they are at with Holiday as their most expensive player going forward.