In a significant shake-up just days before the NBA Draft, the Boston Celtics have reportedly traded All-Star guard Jrue Holiday to the Portland Trail Blazers. The deal sends Holiday to Portland in exchange for guard Anfernee Simons and two future second-round picks, according to ESPN’s Shams Charania. This marks Holiday’s second brief stint with the Trail Blazers, having been acquired by them in the 2023 Damian Lillard trade before being promptly rerouted to Boston.
The trade, which was widely reported on June 23, 2025, signals a strategic pivot for both franchises. For the Boston Celtics, the primary motivation appears to be financial flexibility and long-term roster management, especially in light of Jayson Tatum’s torn Achilles injury suffered in the Eastern Conference semifinals against the New York Knicks. With Tatum expected to miss a significant portion, if not all, of the 2025-26 season, the Celtics are looking to reduce their luxury tax burden.
Anfernee Simons, 26, is set to earn approximately $27.7 million in the upcoming 2025-26 season, which is the final year of his current contract. This is roughly $5 million less than Holiday’s salary for the same period. More critically, the move is projected to generate over $40 million in tax savings for the Celtics in the 2025-26 season, as reported by ESPN’s Bobby Marks. Despite these savings, Boston is still projected to be about $18 million above the second tax apron, indicating that further cost-cutting moves involving other key players might be on the horizon, as Charania also noted.
Simons arrives in Boston as a talented offensive player, having averaged 19.3 points and 4.8 assists per game last season as Portland’s primary scorer. His career 3-point shooting percentage of 38.1% on 6.5 attempts per game aligns well with the Celtics’ aggressive long-range shooting philosophy, as they led the league in 3-point makes and attempts last season. He could immediately step into a significant offensive role while Tatum recovers, and he is also eligible for a contract extension starting in July.
For the Portland Trail Blazers, acquiring Jrue Holiday, 35, suggests a step towards increased competitiveness after missing the playoffs for four consecutive seasons. While Holiday’s offensive production saw a dip last season, averaging 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals, his value lies in his elite defense and veteran leadership. A two-time NBA champion (2021 with the Bucks, 2024 with the Celtics), six-time All-Defensive selection, and two-time All-Star, Holiday is highly regarded as a teammate and a strong defensive presence, which aligns with coach Chauncey Billups’ desire to improve the team’s defense.
Holiday’s contract is substantial, with $32.4 million due in 2025-26, $34.8 million in 2026-27, and a $37.2 million player option for 2027-28. While some analysts question the long-term fit given Portland’s young core, including Scoot Henderson and Shaedon Sharpe, the Blazers could potentially utilize Holiday as a mentor or even explore flipping him to another contender before the trade deadline, though initial reports from Jake Fischer suggest Portland intends to keep him to bolster their push for a playoff spot.
The two second-round picks involved in the trade are the New York Knicks’ 2030 pick and the Trail Blazers’ own 2031 selection. This trade marks one of the first major moves of the NBA offseason, following the Kevin Durant trade, and comes just ahead of the NBA Draft on Wednesday and the start of free agency on June 30.
