The Boston Celtics, one of the most storied franchises in NBA history, are back in the spotlight—but not solely for reasons involving their current pursuit of another NBA title. While the team is locked into the 2025 NBA Playoffs, one name has stirred a wave of controversy and internal debate among the Celtics organization and its fanbase: Cooper Flagg.
Flagg, the projected No. 1 overall pick in the 2025 NBA Draft, has drawn unprecedented hype due to his jaw-dropping performances at Duke, his elite athleticism, and an on-court charisma that many have already compared to legends like Larry Bird and Kevin Garnett. But the problem? Some within the Celtics camp—including key former players—are growing concerned that Flagg’s meteoric rise might pose challenges, both in terms of team chemistry and the franchise’s long-term strategy.
Here’s a closer look at why Boston—despite being an NBA title contender—is having second thoughts, concerns, and heated internal discussions about Cooper Flagg.
The Cooper Flagg Phenomenon
At just 17 years old, Cooper Flagg reclassified into the 2024 recruiting class and joined the Duke Blue Devils for the 2024–25 season. The decision turned out to be a masterstroke. From the moment he stepped on the floor in Cameron Indoor Stadium, he dominated. His impact was immediate: averaging 20+ points, 9 rebounds, and 4 blocks per game, Flagg quickly positioned himself as the clear No. 1 prospect in all of basketball.
Scouts raved about his feel for the game, two-way versatility, and the intensity with which he played every possession. He could guard multiple positions, knock down threes, and run the fast break like a seasoned pro. The NBA began salivating.
Naturally, the Boston Celtics—Flagg’s home-state team, as he hails from Newport, Maine—entered the conversation.
Fans in New England began dreaming of the perfect marriage: the Celtics, powered by Jayson Tatum and Jaylen Brown, drafting the prodigy from Maine and ushering in a new golden era. But behind the scenes, that fantasy is colliding with some very real tension.
A Franchise at a Crossroads
On paper, it may not make sense why a team like Boston, currently a dominant force in the Eastern Conference, would have any concerns about adding a talent like Flagg. After all, wouldn’t any team want to bring in a generational star?
The problem lies in the Celtics’ current core and future direction.
Boston is built around two All-NBA stars in Jayson Tatum and Jaylen Brown, both of whom are under massive long-term contracts. Tatum is set to become one of the highest-paid players in NBA history, and Brown already signed a record-setting deal. They are in their primes, and the Celtics are clearly operating in a win-now mode. Their goal isn’t development—it’s rings.
This raises the critical question: Would the addition of a high-profile rookie like Cooper Flagg disrupt what has already been built?
Former Celtics great and current NBA analyst Paul Pierce weighed in on ESPN last week, saying:
“Flagg is going to be a star. No doubt. But you can’t throw a teenager into a locker room built for a championship and expect everyone to adjust. There’s ego, there’s leadership hierarchy, and there’s urgency. Tatum and Brown have earned this stage.”
Behind closed doors, sources close to the Celtics front office suggest similar sentiments have emerged. While Brad Stevens, the Celtics’ President of Basketball Operations, respects Flagg’s upside, there’s debate over whether adding a rookie into a locker room full of seasoned veterans—like Al Horford, Jrue Holiday, and Kristaps Porziņģis—would be the right move strategically or culturally.
The Local Hero Pressure Cooker
Another issue compounding the situation is Flagg’s local hero status.
With Flagg growing up in Maine and shining under the New England spotlight during his high school and AAU years, the expectation for him to land with Boston is enormous. Local fans and media have all but claimed him as the Celtics’ future cornerstone.
And therein lies the problem.
Flagg hasn’t even played an NBA game yet, and already, the expectations in Boston are sky-high. If the Celtics were to draft him—either through a shocking lottery acquisition or blockbuster trade—the pressure on Flagg would be immense. He wouldn’t just be a rookie. He’d be expected to become the next Bird, the next Pierce, the next Tatum, all in one.
One Eastern Conference executive put it bluntly:
“The Celtics would have to be careful. If Flagg comes in and doesn’t dominate immediately, or if he takes touches away from Tatum or Brown, there could be a media storm. And if Boston stumbles even slightly in the postseason, fans would turn on someone. That someone could be Flagg.”
Chemistry Concerns: The Tatum and Brown Dilemma
Another underlying issue is the dynamic between Cooper Flagg and Jayson Tatum.
Tatum is the face of the franchise and a player many see as the best small forward in the NBA. Flagg, standing at 6’9” with guard skills, plays a similar position. His presence could be seen as a threat—or at the very least, a complication—in terms of rotations and usage.
Multiple insiders have hinted at the Celtics’ front office being wary of repeating past mistakes, referencing the 2018–19 season when team chemistry unraveled with too many mouths to feed (remember Kyrie Irving, Gordon Hayward, and young Jayson Tatum?).
There’s also the risk of creating tension between Brown and Flagg. Brown has long played in Tatum’s shadow despite being a superstar in his own right. If Flagg were to be drafted, Brown might see it as another slight—another sign that the franchise is always looking toward the next big thing instead of embracing the present.
Cooper Flagg’s Camp Speaks Out
So what does Flagg think about the Boston chatter?
Publicly, the teenager has remained diplomatic. In recent interviews, he praised the Celtics organization and called Tatum one of his favorite players growing up. But his AAU coach and mentor made some waves recently when he spoke to The Athletic:
“Cooper’s goal is to go somewhere that believes in him fully—not somewhere that drafts him to appease the media. He wants to earn his place, not be handed it because he’s local.”
Some interpreted that as a veiled message to the Celtics.
Could the Celtics Actually Avoid Drafting Him?
It’s rare to see a team with championship aspirations even within reach of the No. 1 overall pick. But hypothetically, if the Celtics were to trade into the top spot—or if another team with the pick came calling—would Boston even say yes?
Several league sources believe the Celtics might actually pass on Flagg in favor of a trade package that includes veteran help or future draft flexibility. The reasoning is simple: the window to win is now. The Celtics are chasing Banner 18, not developing rookies for 2028.
One anonymous front office member from a Western Conference team told The Ringer:
“If Boston somehow lands the No. 1 pick, I’d bet money they trade it. They’re in the middle of a title run. Why blow that up to develop a 19-year-old?”
A Potential Star They Can’t Ignore
Yet, for all the drama, there’s still a very real possibility that Flagg could become the player Boston eventually needs. Al Horford can’t play forever. Porziņģis has a history of injuries. And Holiday is aging. Cooper Flagg, meanwhile, could be a transformational player—one that gives the Celtics a bridge from the Tatum era to the next generation.
And there’s one more thing to consider: Flagg wants to win. He’s a tenacious competitor with a reputation for grinding in the gym and prioritizing defense just as much as scoring. That kind of mindset is exactly what Boston has built its culture around.
So while some Celtics veterans and execs may see potential problems, Flagg might just be the solution to sustaining the franchise’s elite status long after the current core ages out.
Final Thoughts: A Complicated Future
The Boston Celtics are a juggernaut again. The dream of Banner 18 is alive and well. But even as they chase a championship in 2025, the specter of Cooper Flagg looms large.
A generational talent. A homegrown hero. A potential disruptor—or savior.
Only time will tell whether Flagg and the Celtics are destined to unite or fated to pass each other like ships in the night.
But make no mistake: in Boston, the name Cooper Flagg is already creating waves. And the Celtics have a very real, very major problem to solve.
