Cooper Flagg’s Boss Moves: Getting Ready With the Basketball Star Ahead of the 2025 NBA Draft

Cooper Flagg, the 6 9" basketball phenom from Maine, has arrived at the 2025 NBA Draft in New York City.

At just 18, Flagg has become one of basketball’s most-discussed names (for his prodigious talent, yes, with many calling his skill “generational,” but there’s also a lot of chatter about his reported making of well over $20 million already in NIL income thanks to his standout season at Duke University). Now, as he jumps from Blue Devil to the pros, the spotlight is intensifying. But he seems ready to meet this new threshold.

“I collect myself with breathing,” says Flagg over a phone call when asked about how he handles pressure, whether on or off the court. “I worked on that a lot last year.”

Photo: Getty Images

He sounds pretty relaxed as he’s en route to Midtown’s Lotte New York Palace for a fitting with Boss, which outfitted him this evening in a made-in-Italy three-piece suit of deep navy stretch wool and a silk jacquard tie. It’s the first of a few select dressing occasions between Flagg and the label—further strengthening of Boss’s sporting focus. (The company has also partnered with football’s Patrick Mahomes and Cam Ward, and tennis’s Taylor Fritz.)

“I have seen and paid attention to different guys’ outfits—what they’re wearing in the tunnel,” says Flagg. “I’m excited to step up my game and be ready for next year. I think my style, or what I like for portraying myself, is to stay classy, sharp, even simple.” Flagg cites Orlando Magic forward Paolo Banchero’s aesthetic as a good example.

Flagg is known for his all-court game and notable defending power. He was named an All-American athlete while at Duke, and was also awarded the prestigious Naismith College Player of the Year. While he does not call out one specific basketball idol or role model, Flagg does say he’s been inspired by “pieces” of certain player’s games, namely Kevin Durant and Jayson Tatum, and that if he wasn’t in the arena, he’d likely be playing golf (he’s a 14 handicap, and improving).

As for his high-intensity drive? He attributes it to something those of us with brother and sisters might all recognize: good old-fashioned sibling rivalries (Flagg has a twin named Ace and an older brother named Hunter).

“My parents taught us to just put everything into it that we had—to just give it a hundred percent all the time,” says Flagg. “And that came down to just being in the driveway with my brothers, playing one-on-one. We were having fun, but we were really competing.”