The Portland Trail Blazers acquired Jrue Holiday in a surprising trade with the Boston Celtics last summer, immediately leading many to wonder whether they'd flip the veteran guard yet again. Despite the rumors, Holiday remained in Portland as the Blazers front office acquired him with the intention of keeping him this time around. That proved to be the right decision, as Holiday successfully boosted his value thanks to a relative bounce-back campaign in Portland.
Although his athleticism has declined, Holiday remains one of the best two-way guards in the league. He has the positional size, versatility, and championship experience that every team covets. That well-rounded game came in handy this season, as Portland's backcourt was depleted, with Holiday keeping them afloat by stepping up as a playmaker.
This season proved Holiday's value in Portland. Still, it leaves them in a tricky spot heading into the offseason, as they're expected to receive trade interest in Holiday.
Could the Blazers trade Jrue Holiday again?
Deciding whether to trade Holiday is the toughest decision Portland's front office has to make this summer. In some ways, it's an extension of the decision about which timeline to prioritize for the Blazers.
One issue in their rebuilding process is how heavily Portland's roster depends on its veterans. Outside of All-Star Deni Avdija, Holiday and Robert Williams III were the two players who consistently showed up in their first-round series against the San Antonio Spurs.
The Blazers find themselves somewhat in no man's land: they have a young core that's too talented to bottom out for a coveted draft prospect, but the ceiling of that young core isn't yet high enough to contend.
Holiday has been a great addition to help bridge the gap, providing them with a short-term boost to return to the postseason while continuing to prioritize their future with his veteran leadership, impacting the development of Scoot Henderson, Shaedon Sharpe, and others. Portland could stay the course with Holiday as the bridge between timelines, but a few factors this summer make the decision less straightforward.
The case for a Jrue Holiday trade
For one, Holiday is only going to get older and more expensive. This offseason presents a sell-high opportunity for Portland, especially since he's dealt with injuries the past few seasons.
Additionally, Damian Lillard's return makes Holiday's veteran role on this Blazers roster more redundant. They could decide to keep Lillard as a cheaper solution for those short- and long-term goals, though their defensive identity would certainly take a hit.
Lastly, the Western Conference Finals have shown just how far Portland is away from San Antonio and Oklahoma City. Trading Holiday while they still can for young assets could be the best approach, even though it would negatively affect Lillard's chances of winning during his closing window.
New owner Tom Dundon wants this team to establish a winning culture, and there's few better options in the league than Holiday when it comes to winning. How much does that play a role in this decision?
Portland should first explore trading Jerami Grant
The answer to trading Holiday, surprisingly, could come down to the market for Jerami Grant.
Grant and Holiday are far and away the two highest-paid players on the Blazers roster. Eventually, Portland needs to renegotiate and extend Avdija. It makes sense to trade either Grant or Holiday to provide more financial flexibility and ensure they are able to lock down their All-Star long term.
If Grant remains a negative asset, Portland may not want to sacrifice assets to dump the forward, as has been the case in the past. They could then shift their focus to Holiday, who has more value around the league.
Portland wants to win now, and Holiday helps them achieve that goal. But given their messy two-timeline approach and limited ceiling, the decision on whether to keep him around isn't as black-and-white as it seems.
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