The Boston Celtics traded Jaylen Brown to the Philadelphia 76ers on Wednesday. It was one of those deals that splits a fanbase right down the middle. Paul George and four draft picks came back. A lot of people in Boston hate it. But one of the most famous Celtics fans in the world, Bill Simmons, can’t even get his dad to talk about it.
Simmons posted an update on X that was part joke, part sad reality. He was planning to have his dad, known to listeners as Dr. Bill, join the podcast the morning after the trade for a proper knee-jerk reaction. Dr. Bill said no. He wasn’t ready. “He might still be at Toscano’s waiting for everyone else to get there, not sure,” Simmons wrote. That’s the kind of line that makes you wonder if Boston’s North End really does have a Celtics grief support group disguised as a restaurant.
Dr. Bill Has Seen a Lot. This One Hit Different.
Dr. Bill isn’t just some random guy with a season ticket. He’s been a Celtics season-ticket holder for decades. He’s shown up on his son’s podcast before to complain about a lifeless Red Sox lineup or mourn another early playoff exit. But losing the 2024 NBA Finals MVP? That’s a different kind of pain. The man needed space.
Earlier in the week, Bill Simmons had pitched an idea. He wanted the Celtics front office to sit down for a three-hour dinner at Toscano’s. The guest list: Jayson Tatum, Jaylen Brown, Joe Mazzulla, Brad Stevens, team governor Wyc Grousbeck, and some front office guy. No agents. No family members. No hangers-on. Just the people who actually matter, talking it out over pasta and red sauce. “The right trade isn’t there,” Simmons wrote. “Shit happened, just talk it out.” Dr. Bill wanted in on that meeting. It never happened.
Now What for the Celtics?
The Celtics now have a pile of draft picks and Paul George on the roster. But it’s late in the offseason and the market for big moves is mostly dead. The Tatum-Brown era is officially over. That’s two All-NBA wings who reached two finals and won one championship together. Now Jayson Tatum is alone on the 2026-27 Celtics. He’ll have to figure out how to carry a team without the guy who took some of the defensive pressure off him every night.
Dr. Bill might come around eventually. Maybe he’ll show up on the podcast after a few days of processing. Or maybe he’s still at Toscano’s, staring at an empty chair, waiting for a meeting that never happened.
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