Suppose Jrue Holiday leads the Blazers to an unlikely playoff appearance, and Portland's lottery-protected first-round pick is conveyed to Chicago in a strong draft class. They would likely have a quick series against the Oklahoma City Thunder, and then what?
Odds are, Portland will come up short of the playoffs for a fifth consecutive season. This is arguably more concerning, as the Blazers wasted Holiday's contract, and still don't have a top pick or the young core progress to show for it.
Just another late lottery pick.
Jrue Holiday trade looks bad no matter how the Blazers' season ends
The Blazers are on track to make the play-in tournament, but it's not as exciting when considering how they have gone about making that a reality. In a sense, they've brute-forced that outcome, relying heavily on Jerami Grant and Holiday. These were supposed to be complementary pieces to help their young core develop, not the focal point of the entire roster.
Some of that has been due to injury, with Grant and Holiday stepping up in increased roles as a result of Scoot Henderson, Shaedon Sharpe, and Deni Avdija all suffering injuries throughout the season. However, these injuries should've presented opportunities for Portland's other youth to step up. We're currently seeing that play out with Holiday starting over Henderson while Sharpe and Avdija remain sidelined.
This is a transitional season for Portland in which the process matters significantly more than the end result. The Blazers are currently in no man's land, roughly where they were last season.
Blazers are in no man's land with Jrue Holiday
If Holiday were out of the picture, they would have had two outcomes: making the postseason because of their young core, proving they are, in fact, ready to take that leap. Or more likely, missing out on the postseason. Their building blocks are too talented to bottom out entirely, but securing a top ten pick in a stacked draft class sounds ideal. Having veterans lead the way to a late lottery pick seems like such a Kings move. That's essentially what they did by bringing in Holiday.
Unlike Sacramento, Portland's future outlook is still promising. They aren't quite in purgatory with room to grow, but the lack of a contender ceiling remains a major concern that many seem to be overlooking in favor of a short-term dopamine hit from Holiday hoops. They need more star power, and for a small-mid market, the easiest way is via the draft.
This isn't even accounting for the $104.4 million Holiday is owed over the next three seasons. That contract doesn't seem horrible right now, given his relative resurgence in Portland following a down year in Boston. We likely won't feel that way when he's on the books for a $37.2 million player option in 2027-28, at which point he'll be 37 years old.
Portland's front office has taken an unconventional approach to rebuilding. To their credit, a lot of those bold decisions are aging well. Holiday is one we are currently second-guessing, not necessarily because of his play, but rather because of how his contract and age fit into Portland's rebuilding timeline.
He's proven he can elevate contenders, with rings to show for it in Milwaukee and Boston. That's not the reality of Portland's roster, making the fit questionable and hindering their rebuilding ceiling.Â