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Celtics Finalize Straight Swap of Jrue Holiday for Anfernee Simons After Medical Review

Boston offloaded Holiday’s $135 million commitment to secure cap relief under the second apron, acquiring Simons’s expiring contract for added financial flexibility.

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Apr 11, 2025; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) shoots the ball against the Charlotte Hornets during the first half at TD Garden. Mandatory Credit: Eric Canha-Imagn Images
Boston Celtics President of Basketball Operations Brad Stevens looks on before Game Five of the Eastern Conference Semifinals between the Milwaukee Bucks and the Boston Celtics at TD Garden on May 11, 2022 in Boston, Massachusetts.
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Overview

  • The Celtics and Trail Blazers finalized a one-for-one trade on July 7 that sends Jrue Holiday to Portland and brings Anfernee Simons to Boston, with the previously included 2030 and 2031 second-round picks removed after Holiday’s medical review.
  • Portland’s examination uncovered health issues that prompted the pick removal but did not void the deal, and Holiday is expected to be fully healthy for training camp.
  • Trading Holiday’s remaining four-year, $135 million extension helps Boston fall below the NBA’s punitive second apron threshold and avoid severe repeater luxury-tax penalties.
  • Simons arrives on a one-year, $27.7 million expiring contract after averaging 19.3 points and 4.8 assists, offering immediate backcourt scoring and a flexible trade asset.
  • Now about $20 million over the luxury-tax line but under the second apron once roster spots are managed, the Celtics are weighing further cap-driven roster adjustments before training camp.