How Jrue Holiday Addition Changes Trail Blazers’ Draft Strategy

On Monday evening, yet another NBA domino fell in the form of a cross-conference trade.

In a somewhat surprising move, the Portland Trail Blazers re-added win-now guard Jrue Holiday to their roster, sending out longtime scorer Anfernee Simons and two second round picks to the Boston Celtics.

Portland had previously acquired Holiday, but shipped him off to Boston for two seasons, where he helped the Celtics to a championship. Should Portland opt to keep Holiday — which all signs point to, given they likely had other options in trading Simons — it could very well change their strategy at this year’s 2025 NBA Draft.

Holiday, at 35, remains a win-now player. While his offensive output has seen a slight dip in recent years, he remains one of the best guard defenders in the league. And should be set to infuse the Trail Blazers backcourt with some much-needed two-way prowess. The two-time champ will especially be a seamless defensive fit in Portland, who finished as one of the top teams on that side of the ball to end the 2024-25 season.

Where Portland could’ve potentially gambled on another backcourt piece at the draft this year, they likely won’t now with Holiday rostered.

The Trail Blazers will select at No. 11 this year, and while their best available player is more likely to be a wing or forward, there was a chance talented guards could’ve slipped outside the top-10. Illinois guard Kasparas Jakucionis and Oklahoma's Jeremiah Fears both come to mind as player's that likely hold top-10 stock, but are a few teams passing away from reaching Portland.

Now, the Trail Blazers may be best served to go ahead and swing on bigger prospects that could help to anchor the interior with Donovan Clingan, or provide a scoring punch from the wing. Cedric Coward, Carter Bryant, Asa Newell and more are a few names that come to mind regarding the No. 11 pick.

Regardless, the Trail Blazers should be able to leave the ’25 draft with a solid player, given the depth of the lottery this year.