NBA Draft Eve Blockbuster: Celtics Send Jrue Holiday Back to Blazers in Salary-Shedding Deal for Anfernee Simons

In a surprising move just hours before the highly anticipated NBA Draft, the Boston Celtics have reportedly agreed to trade All-Star guard Jrue Holiday to the Portland Trail Blazers. According to ESPN’s Shams Charania, the Celtics will receive dynamic scorer Anfernee Simons and two second-round picks in return, marking a significant financial maneuver for Boston.

This deal sends Holiday back to Portland for the second time in his career, having been briefly acquired by the Blazers in the 2023 Damian Lillard trade before being rerouted to Boston. Now, he returns to a rebuilding Blazers squad that appears to be accelerating its timeline for competitiveness after missing the playoffs for four consecutive seasons. While Holiday, 35, may not be in his prime, his elite defense and highly regarded leadership qualities could be invaluable for Portland’s young locker room.

For the Boston Celtics, this trade is primarily a strategic financial decision, especially in the wake of Jayson Tatum’s recent torn Achilles injury suffered in the Eastern Conference semifinals against the New York Knicks. With Tatum’s absence significantly impacting their immediate title contention hopes, Boston is aggressively working to reduce its salary cap obligations against the second apron. Anfernee Simons, nine years younger at 26, earns approximately $5 million less than Holiday and is on an expiring contract, offering substantial cap relief. Per ESPN’s Bobby Marks, Boston is now roughly $18 million above the second apron for next season, and this move is a clear step towards getting below that threshold.

Simons, who averaged 19.3 points per game last season as Portland’s primary offensive threat, is expected to fill a crucial scoring role for the Celtics as they navigate Tatum’s recovery. The NBA landscape is currently in flux, with trades beginning to materialize rapidly. Kevin Durant’s recent move on Sunday set the stage, and this Holiday-Simons swap is the first major shake-up since the NBA Finals concluded. With Boston still facing a challenging financial outlook and several Eastern Conference rivals looking to strengthen their rosters, further significant trades involving the Celtics or other contenders should not be surprising as free agency approaches.

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