Jrue Holiday is heading back to Portland.

The Boston Celtics have agreed to trade the veteran guard to the Trail Blazers in exchange for Anfernee Simons and two second-round draft picks.

It’s a full-circle move for Holiday, who was briefly a Blazer after arriving in the 2023 blockbuster Damian Lillard trade before being shipped to Boston. Now, nearly two years later, Portland gets its man back — and with him, a championship-winning presence.

The Celtics, meanwhile, take a calculated step in reshaping their roster. Simons arrives in Boston on an expiring contract and brings a reliable scoring punch from deep — a strong fit for coach Joe Mazzulla’s three-heavy offence.

The 26-year-old has hoisted nearly nine threes a night over the past three seasons.

The move also makes financial sense for Boston. By moving off Holiday’s contract — which carries about $72 million over the next two seasons — the club trims roughly $40 million off its luxury tax bill for next year, according to ESPN.

Portland, on the other hand, adds a proven two-way guard entering his 17th NBA season. Holiday played a crucial role in the Celtics’ 2024 title run, earning All-Defensive honours and shooting a career-best 42.9% from three-point range. He averaged 13.2 points on efficient 50-40-90 splits last season.

For the Trail Blazers, Holiday brings leadership and elite defence to a young group that made strides late in the season. From mid-January onward, Portland went 23–18 and ranked third in defensive rating and transition defence, per ESPN Research.

This is just the beginning for Boston. With Jayson Tatum recovering from an Achilles injury, the team is expected to be active throughout the offseason. Trade talks are reportedly ongoing around several key players.

Simons could help fill a scoring gap, while the financial breathing room opens the door for bigger moves ahead. As for Holiday, he gets a chance to guide a rebuilding Portland squad — one that now has experience to match its youth.