Holiday is being sent back to the Trail Blazers by a Boston team that could now be in transition, a person with knowledge of the details said early Tuesday,
ESPN reported that the Celtics would get Anfernee Simons and two second-round picks from the Trail Blazers.
The departure of Holiday, who made his sixth career All-Defensive team selection in his first season in Boston, was confirmed to The Associated Press on condition of anonymity because the deal is not yet official.
Holiday was traded by the Milwaukee Bucks to Portland in September 2023 when the Bucks acquired perennial All-Star Damian Lillard. Holiday was then dealt days later to the Celtics, moving right into the starting lineup and eventually earning his second career title last June.
But the Celtics have now lost a second member of that starting lineup for at least part of next season, with All-NBA forward Jayson Tatum having surgery after an Achilles tendon injury in the loss to the New York Knicks in the Eastern Conference semifinals.
Simons could provide some of the scoring punch the Celtics have lost, having averaged 19.3 points last season after going for a career-best 22.6 per game in 2023-24.
But the Celtics will miss the defense and leadership that Holiday provided. The two-time Olympic gold medalist’s scoring was down though, with the 11.1 points he averaged last season his lowest since his rookie season in 2009-10, and more than eight points lower than the 19.3 he put up in 2022-23 with the Bucks, when he was an All-Star.
More than that, the Celtics were likely motivated to trade Holiday because of the $104.4 million owed to him over the remaining three seasons of the contract extension they gave him last year, on top of the huge deals for Tatum and Jaylen Brown.
Holiday, who helped the Bucks win the 2021 NBA title, has averaged 15.8 points in a 16-year career that also includes stints with Philadelphia and New Orleans.
The Athletic’s Jared Weiss reported that the Sacramento Kings, Dallas Mavericks and Toronto Raptors were all interested in Holiday before the 16-year veteran ended up with a Trail Blazers team that previously dealt him in 2023 shortly after acquiring the guard from the Milwaukee Bucks in the Damian Lillard trade. He’ll now join his fifth NBA franchise after stints with the New Orleans Pelicans, Philadelphia 76ers, Milwaukee Bucks and the Celtics.
