The first domino has fallen for the Boston Celtics. It won’t be the last.
The Celtics started the anticipated overhaul of their championship core late Monday night by dealing Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and a pair of second-round picks, per ESPN’s Shams Charania.
The Celtics get off the three seasons and $100-plus million remaining on Holiday’s contract but save just $4.7 for the upcoming 2025-26 season. Boston now sits $18 million over the second apron line, which suggests there’s more dealing in the team’s future.
That the Celtics were able to trade Holiday back to the Blazers, the team that essentially redirected him from Milwaukee before Boston’s 2023-24 title season, is amusing. That president of basketball operations Brad Stevens was able to acquire draft assets as part of the deal, after heavy speculation that Boston would have to attach a first-round pick to move Holiday, is even more noteworthy.
If Simons sticks in Boston, he feels like the type of player the Celtics can take a hard look at over the first months of the season. The 6-foot-4 shooting guard turned 26 earlier this month and has averaged 20.7 points per game over the last three seasons.
Simons averaged 19.3 points per game in 70 appearances for the Blazers last season, and despite a downturn in his shooting efficiencies, he has shot 38.1 percent from beyond the 3-point arc for his career. He could potentially help fill some of the scoring void while Jayson Tatum recovers from Achilles surgery.
If the Celtics don’t see Simons as a long-term fit, or if they eventually need to explore a subsequent deal to trim more money, he could have value to other contenders as an expiring contract.
Holiday was a key part of Boston’s success over the past two seasons. He saved some of his finest basketball for the 2024 Eastern Conference Finals against the Pacers, where he routinely made the sorts of winning plays that helped Boston produce a harder-than-it-looked sweep of a team that made the Finals this year.
But it was obvious entering the summer that Holiday’s time in Boston was coming to a close.
The Celtics got ahead of the new collective bargaining agreement by acquiring Holiday on the eve of training camp in 2023. Stevens rewarded him with a long-term extension before Boston’s title run. The Celtics will miss Holiday’s defensive versatility. He paired well with Derrick White in the defensive-minded “Stock Exchange” backcourt.
Simons is a solid playmaker who averaged a career-best 5.5 assists two seasons ago. He ranked in the 80th percentile in assist percentage among all combo guards this past season, per Cleaning The Glass data.
The question is whether he can play defense to a level that allows Joe Mazzulla to confidently lean on him. Opponents shot 50.6 percent against Simons last season, or 4.4 percent higher than expected output, per the NBA’s tracking data.
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