Long before he committed to Duke, Cooper Flagg was already cemented as the undisputed No. 1 pick in the 2025 NBA Draft. A superhuman talent who dominated the high school scene, Flagg didn’t draw LeBron James comparisons — he simply carved out his own lane as a one-of-a-kind prospect.
The reality is clear: Whoever lands Flagg will face immediate pressure to transform from a rebuilding team to a playoff contender.
Just look at the San Antonio Spurs, who wasted no time after drafting Victor Wembanyama, adding both Chris Paul and De’Aaron Fox to accelerate their timeline. Meanwhile, the Orlando Magic are laser-focused on building around Paolo Banchero, ensuring their young core is equipped to compete for years to come.
The main objective?
Make Cooper Flagg so comfortable that free agency never crosses his mind.
Bill Simmons' bold prediction: Flagg to Boston?
Enter Bill Simmons, a lifelong Boston Celtics fan, who recently floated a rustic (and biased) prediction for Flagg’s future:
“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
"I’m counting on Kelly Flagg to stick to her guns—the Celtics, a team she loves very, very much... five years, just plays with whoever drafts him, jumps right to the Celtics at age 24."
On the surface, it’s an idea with little validity—a classic homer take from a Celtics fan. But the bigger question is whether there’s any real possibility Flagg eventually bolts for another team.
The 2025 NBA Draft lottery is shaping up to be a three-team race between the Utah Jazz, Charlotte Hornets, and Washington Wizards. All three franchises have struggled to build sustained success, even after acquiring top-tier talent. Unless one of them makes a drastic shift in direction, it’s not impossible to imagine Flagg eyeing a bigger market or a proven contender down the line.
Would the Celtics make sense?
If Simmons’ theory plays out, where would Boston be in five years?
By 2030, Boston’s core will be at a crossroads:
- Jaylen Brown will be 33
- Jayson Tatum will be 32
- Payton Pritchard will be 32
- Kristaps Porziņģis will be 34, assuming injuries don’t cut his career short
- Jrue Holiday & Al Horford will likely be gone
At that stage, the Celtics will still be a competitive team, but their championship window with this core will be closing. If Flagg were to enter free agency, he’d have a built-in connection to Boston, having grown up just 196 miles away in Maine.
Simmons also noted that Boston’s new ownership could be willing to spend big in free agency, potentially offering Flagg a record-breaking contract when the time comes.
The modern NBA has shown that superstars aren’t afraid to move if they feel their situation isn’t leading to championships. Whether it’s Luka Dončić, Giannis Antetokounmpo, or even Wembanyama down the line, loyalty only goes so far when teams fail to put the right pieces around their stars.