Celtics and Trail Blazers Stir NBA Waters with Shocking Jrue Holiday-Simons Swap and Unexpected Draft Pick Surprises

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Holiday had two years left on his current deal with the Celtics, and he’s owed .2 million with a .2 player option on a third year. The move to send Holiday to Portland is projected to save the Celtics about million in taxes next season and move them million over the second apron.AdvertisementHoliday spent the last two seasons with the Celtics, and he played a key piece in their NBA championship run in 2024. Holiday averaged 11.1 points and 4.3 rebounds per game last season, his 16th in the league. He landed in Boston after the Trail Blazers dealt him there following the Damian Lillard trade to the Milwaukee Bucks. Holiday didn’t play a game for Portland the first time.

Holiday spent the last two seasons with the Celtics, and he played a key piece in their NBA championship run in 2024. Holiday averaged 11.1 points and 4.3 rebounds per game last season, his 16th in the league. He landed in Boston after the Trail Blazers dealt him there following the Damian Lillard trade to the Milwaukee Bucks. Holiday didn’t play a game for Portland the first time.

AdvertisementJrue Holiday is making his way back to Portland in a move that’s shaking up the NBA landscape once more. The Trail Blazers and Boston Celtics finalized a trade Monday night that sends Holiday to the Blazers, while Portland parts ways with Anfernee Simons plus a couple of future second-round picks. This isn’t just a routine swap—it’s a strategic pivot for both teams, with Boston gearing up for more shakeups this offseason as they juggle multiple high-profile roster spots. Holiday’s return to Portland is especially intriguing considering he never actually donned a Blazers jersey during his first stint, having been traded to Boston following the Damian Lillard deal. With two years left on a hefty contract and a player option looming, Holiday’s arrival could inject the veteran leadership Portland’s locker room might desperately need, if they decide to keep him around. Meanwhile, Simons, a solid contributor with impressive stats last season, steps into a new chapter with Boston. This swap, bankrolls and prospects considered, is just the opening act in what promises to be a blockbuster offseason saga. LEARN MORE