The Boston Celtics have officially broken up their championship core, with Jrue Holiday becoming the first member of the championship winning team to be traded.
Boston Celtics’ president of basketball operations and general manager Brad Stevens has struck yet again. According to ESPN’s Shams Charania, Boston is shipping veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for guard Anfernee Simons and two second-round picks.
It’s a full-circle moment for Holiday, who was traded to the Portland Trail Blazers in 2023 as part of a three-team swap that sent Damian Lillard to the Milwaukee Bucks. Portland later flipped Holiday to the Celtics in exchange for Robert Williams III, Malcom Brogdon, and two future first-round picks.
The trade doesn’t come as a surprise since the Celtics face financial constraints under the second apron. Holiday, who signed a 4-year $134.4 million contract with Boston in 2024, has two years left on his current deal. After the trade, the Celtics will continue to save $4.7 million in the deal. According to Spotracs Keith Smith, Boston still remains $18 million over the second apron.
The Celtics Clear Cap Space with Holiday Trade
It’s been no secret the Celtics have faced luxury tax consequences, and their core starters of Jayson Tatum, Jaylen Brown, Kristaps Porzingis, Jrue Holiday, and Derrick White were due a combined $198.5 million next season. With that, the Celtics were prompted to cut payroll due to cap pressure.
Holiday, 36, spent the last two seasons in Beantown, and was a core member of the 2024 Championship roster. As a member of the Celtics, Holiday averaged 11.8 points, 3.6 rebounds, 4.4 assists, and 1.0 steals in 131 games with Boston. He now joins a Trail Blazers team thats in clear rebuild mode. With that, Holiday brings much needed championship, veteran leadership, and defensive prowess to a franchise that hasn’t tasted the playoffs since the 2021 season. Coming off a 36-46 season, it’s unclear if Portland will trade Holiday once again.
Starting point guard for the Celtics, Holiday helped shape and cultivate Boston’s defensive identity. Alongside Derrick White, he formed one of the NBA’s most formidable backcourts, often taking on the toughest defensive assignments. Arguably, his greatest moment as a Celtics came in Game 2 of the 2024 NBA Finals, when he exploded for 26 points, 11 rebounds, three assists, one steal, and one block against the Dallas Mavericks. Holiday led the Celtics in scoring, propelling them to a 105-98 victory. Equally impactful on and off the court, Holiday and his wife, Lauren, were heavily involved in the Boston Community.
What’s Next for the Boston Celtics?
I wouldn’t exactly call this a “salary dump,” given the Celtics will receive a prominent scorer in Anfernee Simons. Drafted No. 24 overall by Portland in the 2018 NBA Draft, Simons is just 26 years old. The Celtics not only keep their core assets, but they receive a player that’s nine years younger. A solid scorer for the Trail Blazers, Simons averaged 19.3 points, 2.7 rebounds, and 4.8 rebounds in 70 games last season. Although a slight regression on defense, Simons is a high volume shooter that’s set to enter the last year of a four year $100,000 contract.
Sure, the Celtics will take on Simons’ $27.7 million expiring contract. But with Jayson Tatum tearing his Achilles in the playoffs, the team’s future is suddenly up in the air. After being bounced by theball New York Knicks in the Eastern Conference Semfinals, Brad Stevens once again shows his brilliance. This time reshaping the roster rather than tearing it down. With this trade, Boston has the option to keep Simons and possibly extend him within a specific window. Still, it wouldn’t be surprising if Stevens flips Simons in what could turn out to be the most unexpected deal of the summer.
One thing’s for certain—Brad Stevens proved he’s a mastermind in the front office by moving arguably one of the heaviest, toughest contracts on the roster with Holiday. In the past, Stevens orchestrated multiple trades to acquire crucial Championship pieces in Derrick White, Al Horford, Kristaps Porzingis, and Jrue Holiday.
According to Charania, “the Celtics remain engaged in trade talks involving multiple key players.” With Tatum set to miss a good portion of next season, all options are on the table for the Celtics.
Follow Sara Jane Gamelli on X @SaraJGamelli.
