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Celtics trade Jrue Holiday to Trail Blazers for Anfernee Simons
Celtics trade Jrue Holiday to Trail Blazers for Anfernee Simons
The Boston Celtics’ exodus has begun.
After long-standing speculation that the Celtics were expected to sell off pieces this offseason, the first domino fell, as they traded guard Jrue Holiday Monday evening to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks.
Holiday, 35, had arguably the worst season since his rookie season in 2024-25. He averaged just 11.1 points, 4.3 rebounds, 3.9 assists and 1.1 steals on 44.3 percent shooting, including 35.3 percent from 3-point range and 90.9 percent from the free-throw line.
While he wanted to remain in Boston, Holiday was widely expected to be moved because of age and contract. He is owed over $100 million over his final three seasons, accounting for at least 19.9 percent of the cap each season.
The Trail Blazers, for better or worse, have been trying to trade Simons for nearly a calendar year. Former teammate Jusuf Nurkic previously (half?) joked that the Orlando Magic should target him, but after they swung for Desmond Bane, the 6-foot-2 guard was a mere afterthought.
Good news for Simons is that he does exactly what Boston wants to do offensively–launch 3s. He’s an average (albeit improving) passer and a poor defender, but that’s not why they acquired him.
Simons has averaged 9.5 3-point attempts per 75 possessions each of his last four seasons, sinking them at a 38.1 percent clip. Last year, Simons averaged 19.3 points and 4.8 assists on 42.6/36.3/90.2 shooting splits, giving the Celtics another creator alongside Jaylen Brown while Jayson Tatum heals from a torn Achilles.
As a result, the Boston Celtics shave $4.7 million in cap, but over $40 million in tax savings, according to HoopsHype capologist Yossi Gozlan. The Blazers are $6.6 million below the luxury tax and nearly $15 million away from the second apron.
Boston getting off of Holiday’s contract while acquiring two second-rounders is good business, but I still think they need another move or two if they were really serious about ducking the second apron in 2025-26. Portland, well, I don’t know what they’re doing … and now they will likely be looking to re-route an older, more expensive, less attractive Holiday for the second time in three calendar years.
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