The Boston Celtics have completed a trade, sending guard Jrue Holiday to the Portland Trail Blazers. In return, the Celtics will receive Anfernee Simons and two second-round draft picks, according to league sources.
This transaction marks a quick reunion for Holiday and the Trail Blazers. Portland had originally acquired Holiday from the Milwaukee Bucks as part of the major Damian Lillard trade in 2023, only to trade him to Boston shortly thereafter.
Anfernee Simons joins the Celtics on an expiring contract. Holiday`s contract extends further, with approximately $72 million owed to him through the 2027-28 season. The trade is also reported to have significant financial implications for Boston, potentially saving the team around $40 million in luxury tax payments next season.
Portland`s reacquisition of Holiday comes just two years after they traded him to Boston in a package that included Malcolm Brogdon, Robert Williams III, and two first-round draft picks (which turned into Bub Carrington in 2024 and another in 2029). The complex original trade that sent Damian Lillard to Milwaukee involved Holiday, Deandre Ayton, Toumani Camara, a first-round pick, and two pick swaps.
This move is expected to be one of several for the Celtics this offseason as they work to retool their roster. The team is adjusting following Jayson Tatum`s Achilles injury sustained in the recent playoffs. Sources indicate the Celtics organization remains active in trade discussions concerning several other key players on their roster.
During the 2023-24 season, Jrue Holiday was recognized for his defensive prowess with All-Defensive team honors. He also demonstrated career-best shooting from beyond the arc, hitting 42.9% of his three-point attempts. Holiday was a crucial contributor to the Celtics` championship run that season, averaging 13.2 points with impressive 50-40-90 shooting splits.
Now entering his 17th NBA season, Holiday brings valuable championship experience to Portland`s young core. His presence is also anticipated to significantly bolster the Trail Blazers` defense. Data highlights Portland`s defensive improvement later in the previous season; from January 19 onwards, they held a 23-18 record and ranked third in the league in defensive rating and effective field goal percentage allowed in transition.
For Boston, Anfernee Simons offers a skilled 26-year-old scoring guard, particularly dangerous from long range. Over his last three seasons, Simons has averaged nearly nine three-point attempts per game. This aligns well with Celtics coach Joe Mazzulla`s offensive system, which places a strong emphasis on three-point shooting.