No matter where Jrue Holiday goes, he'll always be beloved among Milwaukee Bucks fans for his role in helping the team win it all in 2021. He should've spent more than three seasons in Milwaukee, though, but the team included him in the 2023 trade for Damian Lillard, and Portland then traded him to Boston, where he was a key member of the Celtics' 2024 title run. Here we are, a few years later, and there's been some speculation that the Trail Blazers might buy out his contract, leading to a reunion.
No, not a reunion with Milwaukee, but Philadelphia, where he spent the first four seasons of his career, but Marc Stein shot that idea down (subscription required) in his latest piece for The Stein Line:
I'm likewise told that recent speculation about a Jrue Holiday buyout from the Trail Blazers is erroneous. It has become a popular online pastime to suggest that such an arrangement is percolating that helps route Holiday back to the team that drafted him — which obviously fancies itself as a Superteam now after the Sixers acquired Brown and James — but league sources say Portland is not about to just usher Holiday onto the open market.
The insider added that Portland has "been messaging for some time" that it intends to keep Holiday.
It sounds like Jrue Holiday is staying in Portland (at least for now)
Milwaukee already has enough regret to deal with from trading Holiday three years ago, a move that didn't pan out at all. If he did return to the East and join the Sixers, it'd serve as yet another reminder the Bucks don't need, especially if they make it as far as they think they will. Giannis Antetokounmpo is gone, so how about we don't have another reason to dwell on what might've been?
Holiday is under contract for at least one more season, as he has a $37.2 million player option for 2027-28 that he will, in all likelihood, pick up. That decision will come next offseason, and in the meantime, it sure sounds like Portland wants to keep him around in its own quest for a title. Granted, it'd take a lot going right for the Trail Blazers to get there, but they will have Lillard back.
Thinking that Portland would actually buy Holiday's contract out was far-fetched to begin with, as he still has plenty of value at 36 years old. Perhaps the Trail Blazers will make him available at the deadline, depending on how the first half of the season goes, but that's still too far off to speculate about.
Sixers fans already have LeBron, so they can stop dreaming about a Holiday homecoming. And as much as Bucks fans love Jrue, it's a whole lot easier to root for him out West than it would be if he made the move back to the Sixers.
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