Celtics trade All-Star guard Jrue Holiday to Trail Blazers in exchange for Anfernee Simons

The Boston Celtics have traded All-Star guard Jrue Holiday to the Portland Trail Blazers in exchange for guard Anfernee Simons, per Shams Charania of ESPN. Boston also received a pair of second-round picks in the trade.

Holiday, 35, is the first Celtic to go as Boston enters an offseason expected to be quite busy. Standing pat would have meant Boston becoming a $500 million team in combined payroll and luxury taxes. The Celtics had been heavily rumored to be interested in dealing away a couple of their expensive veterans to avoid the hefty tax bill. According to Charania, more movement could be on the way.

“An extremely active offseason begins for the Celtics with the trade of Jrue Holiday, who played a critical role in Boston’s 2024 NBA championship,” Charania tweeted. “The Celtics remain engaged in trade talks surrounding multiple key players on the roster, sources said.”

Beyond the financials, star forward Jayson Tatum is expected to miss most, if not all, of next season after suffering a torn Achilles in Boston’s conference semifinals defeat to the New York Knicks. The Celtics need to find a way to best position themselves to make a run in 2026-27 when Tatum is back to full health. The first step was trading Holiday, who is under contract through the 2027-28 season.

Celtics get younger and cheaper by moving Jrue Holiday to Trail Blazers

Holiday signed a four-year, $135 million extension last April, just months before helping lead the Celtics to their record-setting 18th NBA Championship. He appeared in 131 regular season games in his two seasons in Boston. Holiday posted averages of 11.8 points, 4.9 rebounds and 4.4 assists per game. He finished sixth in 2023 Defensive Player of the Year voting. Holiday should be helpful to Portland’s young core headlined by Scoot Henderson and Shaedon Sharpe.

Holiday makes way for Simons, an unrestricted free agent to be after the 2025-26 season. Simons, 26, is entering the final year of a four-year, $100 million deal. A 2018 first round selection straight out of IMG Academy, Simons emerged as a key contributor for Portland.

Simons had a breakout campaign in 2021-22 and led the Trail Blazers in scoring each of the last two seasons. This past season, he averaged 19.3 points, 4.8 assists and 2.7 rebounds per game. Simons is a career 38% shooter from behind the arc.