Jrue Holiday was great in his first season with the Portland Trail Blazers, vindicating a once-controversial decision to acquire him last summer. But is he suddenly more valuable as a trade piece than as a long-term veteran?
The trade went perfectly to plan, as Holiday brought Portland back to the postseason and provided mentorship to its emerging backcourt. That said, it may be better for them to sell high this offseason and shed his contract while they still can.
The Blazers are at a unique spot in their rebuild heading into what will be a pivotal offseason under Tom Dundon. Portland's new owner has an aggressive mindset and hands-on approach, but has hinted that this roster could go in one of two directions: contention or a step back.
"I'm probably more aggressive than most," Dundon said. "If it doesn't exist, then you gotta go about finding the pieces to continue to get better, and then decide if you can get good enough to win a championship or you have to take a step back. Joe [Cronin] and I have talked about this a lot. There's no one way this is going to go."
Blazers must pick a direction this summer
That's the exact approach Dundon should take this summer to get this team out of no man's land. Portland isn't in purgatory as its up-and-coming roster continues to take gradual steps each season. But they also must be realistic about how far away they are from contenders; this short playoff series against San Antonio exposed their limited ceiling, particularly with Deni Avdija as the go-to option.
Keeping Holiday around next season makes more sense if he's part of a championship-level roster. If Portland is able to convince Giannis Antetokounmpo to come to the Pacific Northwest, for instance, the calculus shifts.
But while everyone is looking forward to a franchise-altering summer, it wouldn't be a bad idea to take the roster in the exact opposite direction. One step backward to set themselves up for two steps forward.
Portland will owe veterans Holiday and Jerami Grant a combined $69 million next season; that number jumps up to $73.6 million if they pick up their respective player options in 2027-28. It would be in the Blazers' best interest to move at least one of them to give themselves more financial flexibility. They eventually have to renegotiate and extend Avdija, who is drastically outplaying his current contract.
Holiday was much more impactful than Grant throughout the season, but that's also why he's a better trade chip. He would likely have contenders lining up to acquire his services should Portland make him available. If they can't package Grant for a superstar to become genuine contenders, it would be strategic to consider moving Holiday instead.
He becomes more expendable next season with Damian Lillard's return, as they would still have that veteran backcourt piece to provide a bridge to remain competitive in the short term while also offering valuable mentorship for their youth.
The good news is that Portland has a lot of flexibility in the direction they take this roster this summer. All options should be on the table, including trading Holiday. If that is the direction they take, this would be a good sell-high opportunity, considering he's only getting older and more expensive.
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