Portland's front office has been quiet in past trade deadlines, but fortunately for Trail Blazers fans, that's not the case this time around. Teams are finally making trades with the Feb. 5 trade deadline fast approaching, the most recent of which saw Portland acquiring sharpshooting guard Vit Krejci from the Atlanta Hawks in exchange for Duop Reath and two future second-round picks. This was a great decision by general manager Joe Cronin, as it gives the Blazers much-needed floor spacing from a young player on a team-friendly contract.
But Portland likely isn't done yet.
NBA insider Marc Stein recently reported on X that the Blazers are "in the midst of LOTS of NBA trade matters at the moment." Their next move should be to trade either Jerami Grant or Jrue Holiday to improve their financial flexibility.
Blazers should trade one of their overpaid veterans next
Both are trade candidates, which now presents a golden widow for the Blazers to dump one of their biggest contracts. Grant has boosted his trade value thanks to a resurgent season, while Holiday's likely at peak value as the 35-year-old is only getting older and more expensive.
The Blazers finally have an All-Star on their roster in Deni Avdija, but will eventually need to renegotiate and extend his team-friendly contract. Moving off Holiday or Grant is the easiest way for Portland to retain and upgrade its young core, as both are owed $100+ million over the next three seasons, including player options in 2027-28. That's... not ideal, especially under the new CBA. Keeping Grant and Holiday around as their two highest-paid players for years to come will limit Portland's contender ceiling. That's exactly why one of them must go in the coming days.
The Milwaukee Bucks previously expressed interest in Grant, although it remains to be seen if they will still buy at the deadline with the uncertainty surrounding Giannis Antetokounmpo's future. Meanwhile, the New York Knicks have explored pathways to acquiring Holiday. However, Cronin's track record suggests that Blazers fans should expect the unexpected.
One thing they can expect? A consolidation trade of some sort. Stein adds that Portland plans to convert two-way signees Caleb Love and Sidy Cissoko to standard contracts after the deadline, meaning the Blazers will have to clear two spots from their 15-man roster. That could be an unrelated move, as it will be challenging for Portland to find a package in which they can attach even more outgoing salary to Grant or Holiday.
Regardless of what the exact trade package looks like, it's vital to Portland's long-term outlook that they cut ties with one of their two most expensive players.