The Portland Trail Blazers will acquire guard Jrue Holiday from the Boston Celtics. Per The Athletic, the Blazers agreed to send guard Anfernee Simons and two second-round picks to the Celtics in exchange for Holiday.

Holiday signed a four-year, $135 million contract extension with the Celtics in 2024. He is set to make $32.4 million in 2025-26, $34.8 million in 2026-27 and has a $37.2 million player option in 2027-28. Meanwhile, Simons signed a four-year, $100 million contract extension with the Blazers in 2022 and is set to make $27.6 million in 2025-26, the final year of that pact.

According to ESPN’s Shams Charania, “Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract.” Charania added that the Celtics are still engaged in trade talks “surrounding multiple key players on the roster,” though further specifics are not yet known.

Holiday, 35, entered the league as the No. 17 overall pick by the Philadelphia 76ers in the 2009 NBA Draft, and has spent time with the New Orleans Pelicans and Milwaukee Bucks. He spent the past two seasons with the Celtics after the Trail Blazers dealt him there following the Damian Lillard trade to the Milwaukee Bucks in 2023, (though he didn’t play a game in Portland). The two-time champion, two-time All-Star and six-time All-Defensive Team selection averaged 11.1 points and 4.3 rebounds over 62 starts last season (his fewest since his 2009-10 rookie campaign).

Simons, 26, was the No. 24 overall pick by the Blazers in the 2018 NBA Draft and averaged 19.3 points, 4.8 assists and 2.7 rebounds per game over a career-high 70 starts last season. In 2023-24, Simons averaged a career-high 22.6 points, 5.5 assists and 3.6 rebounds per game over 46 starts.

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