In a move that signals a new chapter for both franchises, the Boston Celtics have traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two future second-round picks.
The trade, finalized just days before the 2025 NBA Draft, is the first major domino to fall in what’s expected to be a busy offseason for Boston. With Jayson Tatum sidelined for most of next season due to an Achilles injury and Jaylen Brown recovering from knee surgery, the Celtics are shifting into a soft reset mode. Shedding Holiday’s contract—worth over $70 million through 2028—saves the team an estimated $40 million in luxury tax penalties.
Simons, 26, arrives in Boston on an expiring deal worth $27.7 million. A dynamic scorer and three-point threat, he averaged 19.3 points, 4.8 assists, and 2.7 rebounds last season while shooting 38.1% from deep over his seven-year career. He gives the Celtics a younger, more cost-effective backcourt option as they retool around their core.
Ironically, Holiday is returning to Portland—briefly his home in 2023 before being flipped to Boston in the Damian Lillard trade. This time, the Blazers plan to keep him. The 35-year-old brings championship pedigree, elite defense, and veteran leadership to a young roster.
Holiday’s production dipped last season (11.1 points, 3.9 assists), but his impact on winning remains undeniable. He was a key piece in Boston’s 2024 title run and is expected to help Portland push for its first playoff berth since 2021.
