Watch: Anfernee Simons Drops 45 in OT Thriller – Is He Portland’s Next NBA Superstar?

H2: A Sudden Shake-Up: Celtics Land Anfernee Simons, Send Jrue Holiday to Portland Multiple outlets are reporting that the Boston Celtics and Portland Trail Blazers have agreed to a headline-grabbing swap that will ship 25-year-old scoring guard Anfernee Simons to Boston in exchange for veteran two-way star Jrue Holiday and two future second-round draft picks. The deal, finalized just days before the 2025 NBA Draft, realigns two franchises with very different timelines and priorities. H2: Why Boston Wanted Simons • Elite perimeter scoring: Simons averaged 19.3 points, 4.8 assists and 2.7 rebounds while shooting 38.6 percent from three this past season, numbers that give the Celtics a third dynamic scorer next to Jayson Tatum and Jaylen Brown. • Youth and contract control: He is entering Year 3 of a four-year, $100 million deal signed in 2022, keeping Boston’s core locked in through 2026 without the risk of Holiday’s upcoming free agency. • Offensive versatility: Simons can run pick-and-roll, space the floor off the ball and thrive in fast-paced lineups—an ideal fit for head coach Joe Mazzulla’s up-tempo, three-point-heavy scheme. H2: Portland’s Perspective For Portland, moving Simons clears a crowded backcourt, hands the keys to rising star Scoot Henderson and adds a proven leader in Holiday, whose defense and playmaking can mentor a young roster. The two additional second-rounders bolster general manager Joe Cronin’s draft capital as the Blazers continue a long-term rebuild. H2: Salary-Cap Math • Boston absorbs Simons’ $25.9 million 2025-26 salary by sending out Holiday’s $38.5 million expiring contract. • Portland creates roughly $12 million in future flexibility, positioning the team to pursue extensions for Henderson and Shaedon Sharpe. • The Celtics now project to sit just under the second apron, preserving their mid-level exceptions for bench upgrades in free agency. H2: On-Court Fit and Projected Rotations Boston Celtics PG: Derrick White / Payton Pritchard SG: Anfernee Simons SF: Jaylen Brown PF: Jayson Tatum C: Kristaps Porziņģis Portland Trail Blazers PG: Scoot Henderson SG: Shaedon Sharpe SF: Matisse Thybulle PF: Jerami Grant C: Deandre Ayton Sixth Man: Jrue Holiday H2: What’s Next The trade cannot become official until the league moratorium lifts on July 6, but both teams are expected to move swiftly to complete physicals and finalize paperwork. Boston will likely explore defensive-minded wings and veteran rim protection with its remaining cap tools, while Portland is rumored to be active in trade talks for additional first-round picks in Thursday’s draft. H2: Bottom Line By flipping Holiday for Simons, Boston prioritizes youthful offense and cost certainty, aiming to keep its championship window wide open. Portland, meanwhile, gains veteran leadership and draft assets to accelerate its rebuild. Expect further dominoes as the 2025 NBA offseason continues to heat up around Anfernee Simons and the freshly retooled Celtics and Blazers rosters.