If the Trail Blazers go star hunting this summer, they'll likely have to include either Jerami Grant or Jrue Holiday's massive contracts as the foundation of a package to make it work financially. However, as NBA insider Jake Fischer recently reported on The Stein Line, the Blazers don't seem to want to trade Holiday (subscription required).
Fischer adds that the Blazers "will field plenty of external trade interest in Holiday," and that how Portland's crowded backcourt shakes out overall remains a mystery.
There's certainly a case for trading Holiday. Damian Lillard's return makes it more difficult for Scoot Henderson to carve out a consistent role, which could be considered a priority next season after the progress he showed this year, particularly in the postseason against the San Antonio Spurs. Trading Holiday would solve a lot of problems at once in terms of their backcourt logjam and financial flexibility. It also presents a good sell-high opportunity for Portland, as he bounced back after a down year in Boston.
That said, the pros for keeping Holiday around in Rip City outweigh the cons.
Blazers should keep Jrue Holiday around
As Fischer notes, the Blazers are confident that the Lillard-Holiday pairing will work next season. They see it as a backcourt strength rather than a problem:
"My read at this juncture is that team officials believe the two veterans can function together nicely. Lillard and Holiday are likewise said to maintain a strong connection after playing in the Tokyo Olympics together and then being dealt for one another shortly before the 2023-24 season."
The fact that Portland finds itself in this dilemma at all is a testament to how much of a win this trade was for Joe Cronin and company. They managed to turn an expiring Anfernee Simons into Holiday, who immediately got them back into the postseason.
Now, Portland is in a win-win scenario: either sell high and turn Holiday into more assets than they could've gotten for Simons last summer, or keep him around as a key piece for what should be a deep playoff run.
Given his championship experience and versatility, we prefer the latter.
Jrue Holiday's versatility makes him a seamless fit
There's a reason Holiday was the missing piece to get both the Bucks and the Celtics over the top: he's simply a winning player who finds a way to contribute in any roster or system. Implementing him into Lillard's return shouldn't be a problem, especially given Holiday's two-way impact and ability to contribute without needing the ball in his hands.
Portland is in a strange position, taking a two-timeline approach to its roster. But there has to be some sense of urgency to win now around Lillard's closing window, and keeping Holiday around is the best way to achieve that.
As promising as Henderson was in certain postseason games, he was equally as concerning in others. While he's proven he belongs in the Blazers' young core going forward, it wouldn't be a bad idea to continue gradually bringing him along until the consistency is there.
If Portland wants to trade an expensive veteran to package for a star or give itself more financial freedom, it should be Grant, not Holiday, who is the odd man out. Holiday would certainly have more trade value on the market, but there's a reason for that. If the Blazers didn't have win-now aspirations, we'd say to simply take the best package available. But now that they're back in the postseason, Portland needs to consider how these pieces help contribute to a deep playoff run.
That series against the Spurs just further confirmed what the Blazers already knew: Holiday is the better bet to help Portland make a deep playoff run while Lillard's window is still open.
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