Bill Simmons Reveals Five-Year Plan to Get Cooper Flagg to the Boston Celtics

Flagg won't be going to Boston. For now.

Duke Blue Devils forward Cooper Flagg (2) shoots the ball during the first half against the Baylor Bears in the second round of the NCAA Tournament at Lenovo Center. | Bob Donnan-Imagn Images

Duke freshman phenom Cooper Flagg will be the No. 1 pick of the NBA draft if he chooses to forgo the rest of his college career. Which means the Boston Celtics will not be in a position to add the Maine product into the fold. Bill Simmons, as he always does, has a longterm plan to get the big man in green and white.

"I'm counting on Kelly Flagg, who's a massive, gigantic Celtics fan," Simmons said on his latest podcast. "[Nephew] Kyle, turn the TikTok camera on. I'm counting on Kelly Flagg to stick to her guns. The Celtics, a team that she loves very, very much. We have never seen somebody come into the NBA draft and just play out their rookie contract, pass up that 'oh I better take that one contract'—no, he loves the Celtics. Five years, just plays with whoever drafts him, jumps right to the Celtics by age 24. We're waiting for him."

“Come home, Cooper! Come home to Boston!”@BillSimmons has a five-year plan to get Cooper Flagg to the Celtics. pic.twitter.com/pYJrPbh1JX

— The Ringer (@ringer) March 26, 2025

"We're going to have the cap space ready," Simmons continued. "We got a new owner. Come home. Come home, Cooper. You don't even have an NBA team yet. Come home to Boston."

Okay, so it's not really the most detailed plan. Flagg's mom really likes the Celtics and that's pretty much the plan. But stranger things have happened and this is a masterclass in podcasting.

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