Portland Trail Blazers Have Obvious Contract Decision to Make Soon

The Portland Trail Blazers did well with their roster heading into the 2025-26 season. Joe Cronin landed Jrue Holiday via trade and drafted Yang Hansen in what were thought to be the two most consequential transactions of the offseason.

In the early going, there's a case to be made that the biggest addition was actually Caleb Love, a rookie out of Arizona and North Carolina, who played five years in the NCAA's semipro NIL/rev-share eras.

Love is making roughly $636,435 on his current two-way contract. He's scoring 9.2 points in under 20 minutes per game. Love averaged over 10 PPG in December, and started his January 2026 off with 22 points, with six threes on 11 attempts from beyond the arc.

What is Cronin and Co, waiting for? Love is a definitive NBA player, and one who deserves a multi-year deal at a low price point to stay in Portland.

Blazers May Need to Swing Trade Before Re-Signing Caleb Love

Maybe Cronin is waiting for someone to take Robert Williams III off his hands before handing Love the extension he's earned with the Blazers. Per The Stein Line's Jake Fischer, Portland is more willing than ever to part with "The Time Lord."

It makes sense. As great as Williams has been, logging a block in each of his last seven games, and going for 13 blocks over a four-game stretch in late November and early December, there are long-term plans for Donovan Clingan and Yang. There may even be a spot for Duop Reath if the Blazers are willing to be patient.

Williams is a free agent in a few months and could be a valuable spark for the right contender. Love is the spark Portland needs to keep for the foreseeable future and nurture.

One will happen before the other. We'll see how much time that'll take.