Dwight Howard Warns Cooper Flagg: Skip the $28M Temptation, Build Your Legacy at Duke

Dwight Howard Urges Cooper Flagg to Return to Duke Amid $28 Million Payday: “He Could Be a Billionaire Before His Rookie Deal Ends”

In the ever-evolving landscape of college basketball, the name Cooper Flagg has become synonymous with both on-court brilliance and off-court business acumen. As the projected No. 1 overall pick in the 2025 NBA Draft, Flagg has already captured national attention—not just for his highlight reels in Cameron Indoor Stadium, but for the astonishing financial windfall he’s amassed before even stepping onto an NBA court.

Flagg, who electrified Duke fans during his freshman season, has reportedly raked in an eye-watering $28 million through name, image, and likeness (NIL) deals. According to veteran sports journalist Howard Bryant, the 6-foot-9 forward inked a $13 million deal with New Balance and a $15 million sponsorship with Fanatics—both of which are expected to transition with him into the NBA. It’s a modern-day case study in branding and basketball, and Cooper Flagg is at the center of it.

But not everyone is ready to see Flagg take the next leap.

On a recent episode of the Nightcap podcast with Shannon Sharpe and Chad Johnson, Dwight Howard—former No. 1 NBA draft pick and future Hall of Famer—threw a curveball into the discussion surrounding Flagg’s future. Instead of championing the next step to NBA stardom, Howard delivered a bold plea: “Cooper Flagg should go back to Duke.”

Howard’s argument? In the age of ever-growing NIL payouts and a rising NBA salary cap, the long-term financial ceiling may be even higher for players who delay entry into the league.

“If he stays two more years and wins at least one championship at Duke, he’s gonna get at least $100 million off college,” Howard said. “Then, when he goes to the league, the salary cap is gonna be higher for rookies. He’s gonna make $500 million. … He’s gonna be a billionaire before he finishes his rookie contract.”

It’s an audacious prediction, but it’s not without merit.

Howard, who signed a three-year, $19.5 million rookie deal with the Orlando Magic in 2004, knows what it’s like to enter the league under a microscope. Two decades later, Flagg is expected to sign a four-year, $62.7 million contract with the Dallas Mavericks—assuming they take him with the top pick, as widely anticipated. And that’s just the beginning. With a renegotiation of the NBA’s collective bargaining agreement on the horizon and franchise values soaring, rookie contracts could see significant spikes in the years to come.

So, should Flagg actually consider Howard’s advice?

From a legacy standpoint, staying at Duke for another season—or even two—could cement Flagg as a college basketball legend. He could chase NCAA championships, National Player of the Year honors, and deepen his connection with fans in a way the NBA grind doesn’t always allow. And with NIL deals rivaling, and in some cases exceeding, NBA rookie salaries, the financial tradeoff may not be as steep as it once was.

Still, the allure of the NBA remains potent. Flagg has been pegged as a generational talent. Scouts see shades of Larry Bird’s basketball IQ, Kevin Durant’s shooting stroke, and the competitiveness of Kobe Bryant in his game. The Mavericks, a team already loaded with Luka Dončić and emerging star Dereck Lively II, see Flagg as the missing piece to a championship puzzle.

Ultimately, the decision will come down to more than just dollars and cents. It will be about vision—how Cooper Flagg sees his journey unfolding, not just as a player but as a brand, a businessman, and a future ambassador of the sport.

Dwight Howard has certainly opened the door to a conversation that, in previous eras, wouldn’t have existed. College basketball, long considered a stepping stone to the pros, has now become a viable alternative route to wealth and influence. For Flagg, the possibilities are endless—and so are the opinions.

Whether he chooses to chase NBA glory in Dallas or build a longer legacy in Durham, one thing is certain: Cooper Flagg is changing the game, both on and off the court.

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