The move marks another major transaction of the NBA offseason after Kevin Durant’s trade to the Houston Rockets and signals a shift in strategy for both franchises following a season of high expectations and postseason disappointment.

Boston reshapes roster, eases tax burden

Jrue Holiday, 35, played a pivotal role in Boston’s 2024 championship run, providing elite defense and veteran leadership. During this last season, he averaged 11.1 points, 4.3 rebounds, and 3.9 assists across 62 starts, earning his sixth career NBA All-Defensive Team selection.

However, with Jayson Tatum sidelined by a torn Achilles and the Celtics facing a ballooning payroll, Boston’s front office prioritized financial flexibility and scoring punch in the backcourt.

By trading Holiday, who has three years and over $100 million left on his contract, Boston reportedly saves around $40 million in salary and luxury tax payments for the upcoming season. The deal also positions the Celtics nearly $18 million below the league’s second tax apron, giving them more room to maneuver in free agency and the draft.

Anfernee Simons, 26, arrives in Boston on the final year of his contract. He averaged 19.3 points and 4.8 assists last season, shooting 36.3% from three-point range. Simons is expected to provide much-needed scoring, especially with Tatum’s status for next season uncertain. His expiring $27.7 million deal also offers Boston additional flexibility going forward.

Portland bets on veteran leadership

For the Trail Blazers, reacquiring Holiday is a bold move aimed at accelerating their rebuild in the competitive Western Conference. Portland originally obtained Holiday in the 2023 Damian Lillard trade but quickly rerouted him to Boston for draft capital.

Now, the Blazers bring him back to anchor a young roster featuring Scoot Henderson, Shaedon Sharpe, and recent lottery pick Donovan Clingan.

Reports indicate the Blazers plan to keep Holiday rather than flip him again, hoping his presence will help the team compete for a playoff spot in the coming season. He joins a lineup that also includes Jerami Grant and Deandre Ayton, giving Portland a blend of youth and experience as they look to climb the Western Conference standings.

This trade underscores the shifting priorities for both franchises. Boston gains a dynamic scorer and greater financial flexibility as they navigate a challenging offseason, while Portland bets on veteran leadership to guide their young core.

With more moves expected from both teams, the NBA offseason is off to a dramatic start.