The Celtics have agreed to trade point guard Jrue Holiday to the Trail Blazers in exchange for guard Anfernee Simons and two second-round picks, multiple league sources confirmed late Monday night.
A league source said that Boston will receive the Knicks’ 2030 second-round pick that the Trail Blazers had previously acquired, as well as Portland’s 2031 second-round choice.
Simons, 26, averaged 19.3 points and 4.8 assists for Portland this past season. He is due to make $27.7 million next season in the final year of a four-year, $100 million contract.
Holiday, 35, signed a four-year, $135 million extension with the Celtics in April 2024 and will make $32.4 million next season.
Boston was projected to be about $20 million over the second apron line, which would lead to several roster-building restrictions, so this move chips away at that number.
The fact that Simons is on an expiring deal, combined with Boston’s clear desire for further cost-cutting, certainly opens the door for Simons to potentially be moved in a subsequent trade. A league source said that the Celtics acquired Simons because they like what he can bring to the team, but added that the team remains engaged on all fronts as it continues to look for ways to upgrade the roster.
For now, though, Boston has acquired a younger, cheaper alternative to Holiday while also adding some assets to its cupboard.
The Trail Blazers acquired Holiday from the Bucks in the massive 2023 deal that sent All-Star Damian Lillard to Milwaukee. That briefly appeared to tip the scales in the Eastern Conference in favor of the Bucks, but the move actually proved fateful after the Celtics turned around and acquired Holiday from Portland, giving the Celtics the final piece they needed to capture their elusive championship last season.
Holiday averaged 12.5 points, 5.4 rebounds, and 4.8 assists during Boston’s championship year and was named second-team All-Defense. He helped Team USA to a gold medal at the Paris Olympics last summer but his numbers dipped a bit this year as he dealt with several nagging injuries.
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