As Boston begins an exciting summer, Bill Simmons sounded a note of approval if he is a gauge of Celtics supporters’ responses to the team’s recent pair of high-profile trades.
The Celtics’ management reportedly traded Kristaps Porzingis and Rue Holiday in back-to-back deals earlier this week in order to reduce salaries and avoid the league’s secondary luxury tax. The founder of The Ringer and a lifelong Boston fan opened his appearance on The Bill Simmons Podcast with a direct assessment of the Celtics’ current situation.
In his introduction, Simmons told Chris Mannix, a reporter for Sports Illustrated and the guest, that the 2024 Celtics funeral was finally here. However, in spite of the difficult news and the protracted recovery period Jayson Tatum will need to endure following his Achilles tendon rupture during the Knicks playoff loss, Simmons was optimistic about the difficult decisions that were being made.
Regarding the Holiday and Porzingis trades, he claimed that they mysteriously stole $28 million in two transactions. They fell under the second apron, which has all these other good roster effects in addition to saving them over $200 million in luxury tax.
He hinted that another trade might yet occur, mentioning Boston role player Sam Hauser as a possible addition to a future agreement (and mentioning the Celtics’ potential wish to re-sign both Luke Kornet and Al Horford).
Simmons seemed excited about the situation when asked about the two transactions the team has supposedly already completed. In particular, he was pleased by how Brad Stevens, the president of basketball operations for the Celtics, was able to reduce salary with just two agreements.
Simmons referred to the moves as a “borderline miracle.”
Simmons remained positive despite losing Holiday and Porzingis, maybe missing at least some of the upcoming season without Tatum, and Jaylen Brown returning after recent knee surgery.
He insisted, “I don’t think the Celtics are going to be that bad next year in this weird Eastern Conference,” but the former journalist conceded that it might simply be his inner Celtics fan coming out.
Citing the title guard’s possible deterioration at age 35, Simmons remarked, “I was looking at the roster and I thought, Holiday in the playoffs and the Knicks series looked pretty rough.” Boston, however, could still contend in a weakened conference after trading him for Anfernee Simons, a potentially key player.
Simmons hypothesized that Jaylen Brown might be saying, “This is my time now, I can carry us.” He came to the conclusion that for a squad that is typically built on tradition and stability, this may be a very unexpected period.
With the 2025–26 Celtics, I believe all bets are out, including additional trades and them simply gutting s***.
Since 2016, Hayden Bird has been employed at Boston.com as a sports staff writer. He covers every aspect of New England sports.
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