The Boston Celtics just wrapped up a whirlwind of a postseason — filled with jaw-dropping performances, late-game dramatics, and the signature grit that’s defined the franchise for decades. But even amid their playoff push, the front office in Boston has already begun to look toward the future — a future clouded by uncertainty but fueled by ambition.
One of the biggest shocks came not on the court, but off it. According to Kevin O’Connor of The Ringer, the Celtics reportedly interviewed top draft prospect Cooper Flagg at the NBA Combine. For those who’ve followed Flagg’s journey, the connection makes poetic sense. A native of Newport, Maine, just a few hours north of TD Garden, Flagg is a New Englander through and through. He’s the prodigal son with superstar potential — and the Celtics are hoping to find a way, any way, to bring him home.
There’s only one problem: Boston holds the 28th pick in this year’s NBA Draft. Flagg, by every reputable metric and mock draft, is a consensus top-three prospect. Most boards have him going No. 1 overall. Unless Brad Stevens has some never-before-seen rabbit to pull out of his front office hat, this would require a seismic draft-day heist. But then again, this is the Boston Celtics. And as one Celtic legend once screamed in green and white confetti: ANYTHING’S POSSIBLE.
Boston’s interest in Flagg makes sense on multiple levels. The 6-foot-9 forward is a generational talent with a two-way game polished beyond his years. At Duke, he showed flashes of brilliance that instantly drew comparisons to legends. He’s tenacious defensively, smart in the half-court, and plays with the kind of motor that Celtics fans worship. He’s a competitor, a leader, and most importantly, a winner.
Flagg once famously said in an interview, “Who wouldn’t want to play for their hometown team?” That team, to him, has always been the Boston Celtics. It doesn’t hurt that his favorite player right now is Jayson Tatum — the very cornerstone of the Celtics franchise, the face of the team’s present and future.
But here’s the rub: Tatum, who tore his Achilles late in the playoffs, is likely to miss all of next season. It’s a brutal blow for a team that has been on the verge of championship glory. Tatum’s injury not only pauses the team’s title aspirations — it also forces Boston’s front office into retooling mode. With one of the league’s deepest rosters and smartest execs in Brad Stevens, the Celtics aren’t going into a rebuild. They’re simply recalibrating — with the hopes that the 2025–26 season sees Tatum return to full strength, perhaps with a new young superstar at his side.
Enter Cooper Flagg.
It’s the dream scenario for Boston. A homegrown phenom with ties to the region, a love for the franchise, and admiration for its superstar. A year of mentorship, growth, and learning while Tatum recovers. Then a relaunch in 2026 with Tatum and Flagg leading the charge — the present and the future in perfect harmony. The symmetry is almost too good to be true.
But to pull off what would be the most daring draft maneuver in recent NBA history, the Celtics would need to find a team at the top of the draft willing to dance. The asking price? Likely astronomical. Think multiple first-round picks, young assets, and possibly even a core rotational piece. It would be a steep price to pay — especially for a team that’s consistently in the championship conversation. But when it comes to Cooper Flagg, some might argue that no price is too high.
In many ways, Boston is gambling on timing. With Tatum sidelined, this is the rare window where the Celtics can afford to take a step back in order to leap forward. It’s an opportunity to inject youth into a veteran-heavy core. It’s also a chance to create a storybook narrative — one that turns tragedy (Tatum’s injury) into a turning point toward something even greater.
And while the odds are stacked, this is Brad Stevens we’re talking about. Since taking over as president of basketball operations, Stevens has made a series of bold, calculated moves that have kept the Celtics at the top of the East. He’s traded beloved veterans, unearthed hidden gems, and constructed a roster that blends toughness with talent. He’s not afraid to take risks — and he’s built enough equity with Celtics Nation to be trusted with a gamble like this.
It’s also worth noting that Boston has always been a franchise defined by its stars. From Russell to Bird, Pierce to Garnett, and now Tatum — the Celtics are at their best when they’re powered by iconic talent. Cooper Flagg, for all intents and purposes, fits that mold. He’s not just a talented player; he’s the kind of transformational figure who can define an era. And the Celtics — with their legacy, platform, and championship DNA — are uniquely positioned to maximize his potential.
From a branding and business perspective, the move would also be monumental. A New England native donning the green and white would electrify the fanbase. TD Garden would buzz with renewed energy. Jersey sales would skyrocket. Media narratives would overflow with comparisons to the legends of the past. For a franchise with 17 championships and a worldwide fanbase, Cooper Flagg would be more than a player — he’d be a movement.
Still, the path remains murky. Even if a top-three team is willing to move off their pick, there’s no guarantee Flagg would fall to the exact slot the Celtics trade into. Other teams — with more draft capital — could outbid Boston. Flagg’s performance at the combine and his existing hype only make it more likely that a bidding war will ensue. Boston will have to be shrewd, aggressive, and perhaps a little lucky.
But if there’s one thing that defines this franchise, it’s the refusal to back down from a challenge. The Celtics have always embraced the improbable. They’ve risen in moments when others wrote them off. They’ve crafted comebacks, shattered expectations, and turned adversity into triumph. The pursuit of Cooper Flagg feels like the next great chapter in that tradition.
It’s not just about adding another talented player. It’s about building for the next decade. It’s about laying the groundwork for the post-Tatum era — or ideally, the Tatum-and-Flagg era. It’s about staying ahead of the curve in a league that’s constantly shifting. And perhaps most of all, it’s about believing that no dream is too big, no move too bold, and no goal too lofty.
As the 2025 NBA Draft approaches, eyes will be on Boston. Will Brad Stevens shock the world? Will the Celtics mortgage a piece of their present to secure their future? Will Cooper Flagg become the latest in a long line of legends to wear Celtics green?
Time will tell. But if history has shown us anything, it’s this: the Celtics don’t follow the rules. They write their own script. And in a draft where all the odds say no — where the analysts dismiss the possibility, where logic takes a backseat — Boston might just prove them wrong.
Because when it comes to the Boston Celtics and their championship dreams, ANYTHING’S POSSIBLE.