The Boston Celtics have made their first big move of the summer — and it’s already turning heads.

Per Shams Charania, Boston is sending two-time NBA champion and defensive anchor Jrue Holiday to the Portland Trail Blazers in exchange for scoring guard Anfernee Simons and two second-round picks.

This marks a full-circle moment for Holiday, who was originally acquired by Portland in the 2023 Damian Lillard trade with Milwaukee, before being flipped to Boston in a deal that landed Portland two first-round picks. Now, after helping Boston secure the 2024 NBA championship, he’s headed back to Rip City — this time, to play.

For the Celtics, Simons offers a new scoring punch on an expiring contract, likely giving Boston more flexibility with both cap space and future trades. It’s an early signal that the defending champs plan to retool — not just run it back.

Meanwhile, Portland gets a proven winner in Holiday who can stabilize a young backcourt and mentor players like Scoot Henderson and Shaedon Sharpe. Whether this signals a push toward competitiveness or a future move remains to be seen.

What we know: both teams are just getting started this offseason.