The Portland Trail Blazers have acquired veteran guard Jrue Holiday from the Boston Celtics in exchange for Anfernee Simons and two second-round draft picks, sources told ESPN’s Shams Charania.

Holiday, a two-time NBA champion and six‑time All‑Defensive Team honoree, averaged 11.1 points, 4.3 rebounds and 3.9 assists last season with Boston, while shooting a career‑high 42.9% from deep. At 35, he returns to a Blazers team seeking veteran leadership and defensive stability on the guard and wing spots.

Portland had originally traded Holiday in the blockbuster Damian Lillard deal of 2023, sending him straight to Boston. Now he’s back, part of a push to mentor the Blazers’ younger core, particularly young guards Scoot Henderson and Shaedon Sharpe, to try and elevate their competitiveness in the Western Conference.

Simons, 26, brings offensive firepower to Boston, where he’ll slot into a 3‑point‑heavy rotation. He averaged 19.3 points and 4.8 assists over 32 minutes per game last season. Boston also received two future second‑round picks as part of the deal.

According to ESPN’s Bobby Marks, the move shaves approximately $40 million in luxury‑tax burden from Boston’s books and moves them roughly $18 M below the second apron, enhancing their financial flexibility.

ANALYSIS: Portland expects Holiday to fortify its defense and locker‑room culture – as the team eyes a return to playoff contention, his résumé and veteran presence could prove instrumental. His presence could prove to be vital for Henderson and Sharpe’s development as they work their way to be stars in the league. Holiday can teach both young guys the defensive acumen and the championship pedigree needed to succeed in the NBA.

For Boston, acquiring Simons means a little bit of cap relief as they float around the second apron of the luxury tax. The 6-foot-5 Simons is also perfect for their system with his three-point shooting and rim pressure both essential elements of their offensive attack.

This move marks a strategic shift for both franchises: Portland prioritizes veteran leadership and defensive toughness, while Boston levers flexibility and younger talent to navigate an evolving roster landscape. Overall, this looks like to be a win-win trade for both teams as they both got what they wanted and addressed a specific need.