Bill Simmons Reveals Multi-Year Plan For Celtics to Land Cooper Flagg

The Boston Celtics are rolling along just before the postseason starts. The team will be looking to repeat as NBA champions, and they have a great chance at doing so.

More news: NBA Insider Says Celtics Could Go After Kevin Durant This Summer

But like any good front office, Boston is thinking about how the future could look. While the Celtics do have a strong core in place, they could fall victim to the new CBA restrictions and be forced to bring this core up.

Every team is looking for the next star or leader of its franchise, but Boston has two of them. However, things could change in the coming years.

One player who is about to enter the NBA could be an option down the line. Duke star forward Cooper Flagg is expected to be the first overall pick in the upcoming NBA Draft.

But longtime NBA personality Bill Simmons has devised a plan to have Flagg land with the Celtics. This would be a few years down the line, but Simmons believes Boston could have a good chance to bring the star forward home.

""I'm counting on Kelly Flagg, who's a massive, gigantic Celtics fan... 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... Five years just plays with 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."

“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

Flagg is from the Northeast and could desire to return to the area down the line. The Celtics would present him with a great opportunity, and it would be a homecoming of sorts.

The Duke star is expected to be the next big thing in the NBA, so this would be a home run for the Celtics if they could land him. Even with this hypothetical plan years down the line, Boston could try to line things up to make a strong run at him.

It remains to be seen how this will all play out but Simmons is already thinking years ahead for Boston.

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For more news and notes on the Boston Celtics, visit Boston Celtics on SI.