Boston native and diehard Celtics fan Bill Simmons is no stranger to bold ideas, but his latest plan might be his most ambitious yet. In a recent episode of The Bill Simmons Podcast, the NBA pundit laid out a tongue-in-cheek—yet oddly plausible—five-year strategy to bring future superstar Cooper Flagg to the Boston Celtics.
“I’m counting on Kelly Flagg, who’s a massive, gigantic Celtics fan. 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, no. No, he loves the Celtics. Five years, just plays whoever drafts him, jumps right to the Celtics by age 24.”
“We’re waiting for him. We’re gonna have the cap space ready, we got a new owner. Come home, come home Cooper. You don’t even have an NBA team yet. Come home to Boston. We’re waiting for you.”
Cooper Flagg, the Duke freshman phenom who just dropped 30 points in a Sweet 16 win over Arizona, is all but guaranteed to be the No. 1 pick in the 2025 NBA Draft. With his combination of size, skill, and competitiveness, Flagg has emerged as the most hyped prospect since Victor Wembanyama.
But with the Celtics likely nowhere near the top of the draft for the foreseeable future, their chances of landing him seem nonexistent—unless you ask Bill Simmons.
Simmons, with his trademark mix of satire and sincerity, is banking on the Flagg family’s Celtics fandom as a long-term recruiting advantage. His vision is simple: Flagg plays out his rookie contract—likely four years plus a team option—and at age 24, heads to Boston as an unrestricted free agent, turning down the typical rookie max extension.
It’s a gamble few rookies ever make, but Simmons is holding out hope that Cooper could be the exception.
Of course, the plan is steeped in fantasy. No player projected to be a No. 1 overall pick has ever declined a rookie extension to join a specific team outright. Financially, it’s a sacrifice few are willing to make. And yet, Simmons isn’t entirely joking. He sees a window where sentiment, timing, and smart cap planning could bring the Maine-born Flagg back to the Northeast in Celtics green.
In the meantime, Flagg is making headlines on the court. He’s averaging 18.7 points, 7.5 rebounds, 4.2 assists, 1.4 steals and 1.3 blocks per game, shooting nearly 49% from the field and 36% from three in his freshman season at Duke. His size, defensive instincts, and elite feel for the game already have NBA scouts salivating.
The Celtics, meanwhile, are a championship contender with a deep, veteran-heavy roster. But Simmons knows as well as anyone that windows close quickly in the NBA. His dream is to keep that window open with a hometown hero in waiting.
So while most Celtics fans are focused on the upcoming postseason, Simmons is already planting the seed for 2030—because nothing says Boston basketball like planning five years ahead and refusing to let go of hope.
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