Whether it's Jrue Holiday or Jerami Grant, the Portland Trail Blazers should trade one of their most expensive players this summer.
Renegotiating and extending Deni Avdija has to be considered a top priority, and moving one of their expensive veterans would help provide them with much-needed financial flexibility. But which one should Portland trade?
That answer should lie in which direction they ultimately take this roster in their first offseason under Tom Dundon. Some are expecting an immediate splash under Dundon, who is, by his own admission, more aggressive than most owners. But at his introductory press conference, Dundon left the door open for Portland to take its roster in either direction:
"And if that [trade] opportunity exists, I’m probably more aggressive than most. If it doesn’t exist, then you’ve got to go about finding the pieces to continue to get better, and then decide if you can do good enough to win a championship or you have to take a step back. Joe and I have talked about this a lot. There’s no one way this is going to go for sure. If we get a star, we have a chance to win. If we can’t find a star, then we’ve got to add some pieces and hope some things develop. And if that doesn’t work, then we’ve got to try again with a new plan, and I think there’s equal chances for all those things to happen.”
In other words, Dundon already knows this team needs to escape no man's land.
Blazers need to lean into one of their two timelines this summer
The NBA's anti-tanking changes to the lottery may have changed the equation a bit, but hovering around .500 is essentially the worst possible situation your team can be in. The Blazers' young core is far too talented to tank for another top draft pick, but they also must continue adding to what is an unfinished roster.
It's encouraging that Dundon isn't dead set on making an immediate upgrade, as it suggests he doesn't have the new owner syndrome to the extent some may think. We've seen new owners set back franchises for years with blockbuster moves that backfired, most notably Phoenix Suns owner Mat Ishbia's all-in move for Kevin Durant.
Option 1: Portland packages Jerami Grant for a star
That said, Portland is already exploring a blockbuster trade, with Marc Stein reporting that they and the Miami Heat are the two teams with registered interest in Giannis Antetokounmpo. If that is the direction Portland takes this summer, then packaging Grant instead of Holdiay is a no-brainer.
If it's Giannis specifically, keeping Holiday around will help convince him to commit long-term to staying in Portland, given their connection as former teammates. But even in general, an aggressive move for a star means Portland is ready to win as soon as next season. Holiday provides much more of an immediate two-way impact than Grant. It will require more future assets to package Grant instead of Holiday, but the Blazers have already committed to a short-term timeline built around their veterans at that point.
Alternatively, the Blazers could prioritize the timeline of their young core, staying the course of what has been a patient rebuild. In that case, trading Holiday instead of Grant is suddenly the more logical decision.
Option 2: Blazers trade Jrue Holiday, prioritize future
Instead of attaching future assets to incentivize a team to take on Grant's salary, Portland can actually come away with more future assets of its own by shipping Holiday.
Despite his age and injury concerns, Holiday showed this season that he has plenty of value left to provide a contender. He also has a proven track record of being the missing piece to win a ring in both stops in Milwaukee and Boston, which could make teams more willing to sacrifice a significant part of their future if they feel Holiday can serve as a similar difference-maker for them.
Dundon has hinted that this team will either take a step forward or backward, which is the right approach as Portland continues to keep its options open. They have the flexibility to take the roster in a variety of directions, thanks to the two-timeline approach and blend of youth and veterans. Still, whether to trade Grant or Holiday should be pretty straightforward, depending on which direction they ultimately decide.
If the Blazers are continuing to rebuild, flipping Holiday for future assets (yet again) makes perfect sense. If they want to acquire a star and win now, keeping Holiday around will help them reach that contender ceiling.
Either way, it's important that Portland picks a lane this summer.
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