Cooper Flagg, a competitive apparel battle and the winning pitch: ‘Like a movie’

Four conference rooms. Three pitch meetings.

All for one chance to land a future star.

Rewind to May 20, 2024, the day three factions of rival apparel company executives descended on the Four Seasons Hotel Los Angeles at Beverly Hills. The purpose of their one-day visit? Woo Cooper Flagg, the then-17-year-old wunderkind widely considered one of basketball’s budding young stars.

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In hindsight — especially after Wednesday night, when the Dallas Mavericks selected Flagg with the No. 1 pick in the 2025 NBA Draft — it feels foolish for anyone to have ever doubted Flagg’s trajectory. But at the time, the 6-foot-8 forward had yet to play a minute of college basketball at Duke. His unofficial breakout at Team USA’s pre-Olympic training camp — where he more than held his own against the likes of LeBron James and Steph Curry — wouldn’t happen for another two months, either.

Still, Flagg oozed such potential that high-profile apparel brands were lining up to work with him when he was just a high school junior. In the fall of 2023, when the Newport, Maine, native opted to reclassify and enroll at Duke a year early — effectively skipping his senior season of high school — NIL (name, image and likeness) offers came fast and furious. Chief among them were major shoe companies like Nike, Adidas and New Balance, all wanting to sign Flagg to their star-studded rosters.

Flagg, his family and his representation wanted that major decision settled before he arrived on campus in Durham, N.C., so he could focus on hoops. That meant devising a solution: They’d hear pitches from three select companies, all on the same day, and then pick their future partner once the meetings concluded.

“Like a movie,” said Naveen Lokesh, New Balance’s global marketing director of basketball and football, who also spearheaded the company’s pitch to Flagg. “Almost like ‘Air.’”

On pitch day, the groups of executives huddled in their Four Seasons conference rooms for final rehearsals. Quietly, New Balance was confident in its pitch — particularly with one secret component, which it hoped would make all the difference.

Lokesh and his team entered a separate conference room where Flagg, his family and his Creative Artists Agency (CAA) team waited to be wowed. Lokesh wasted no time playing the high notes. He reminded the Flaggs how every summer they used to attend a tent sale at New Balance’s factory in Skowhegan, Maine — a half-hour drive from Flagg’s hometown — and pick out sneakers for the upcoming school year. (Kelly, Flagg’s mother, even remembers doing the same when she was a little girl.) Lokesh stressed how important New England was to New Balance, which is based in Boston, as well as the Flagg family. They discussed philanthropy opportunities and product possibilities, and they reiterated that the privately owned brand was not looking to sign Flagg as one of a number of new athletes.

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Rather, New Balance only wanted him. An all-in bet.

“If he goes to another brand,” Lokesh remembered saying, “they’re going to do great storytelling, and they’re gonna have great products. Great marketing, big campaigns. All the things we can do.”

Pause. Secret weapon time.

“There’s one more thing we want to show you,” Lokesh continued, “that nobody else can show you or give you. It’s a small message.”

Suddenly, a video started playing of the Skowhegan factory, countless assembly lines within it and the process of a custom pair of basketball shoes being made. At one point, the father of one of Flagg’s former grassroots teammates — who still works at the facility — made an appearance. Then another worker shortly thereafter, proudly proclaiming that, “Cooper Flagg being from Maine and being the basketball prodigy that he is, it just gives you that sense of pride.” Eventually, the 53-second clip ended with a still shot of the gray shoes, with “FLAGG” stitched directly onto the tongue.

As the lights came up inside the Four Seasons conference room, Lokesh pulled out his grand finale: The pair of custom shoes from the video, straight from Maine, still the only pair of Cooper Flagg New Balances in existence.

“It was pretty cool to see that video and the Maine shoes and some familiar faces,” Flagg told The Athletic. “That meeting, going through their plans and kind of the future they saw for me, it just aligned really well with the future that I saw for myself.”

In December 2023, two months after Flagg committed to Duke, Lokesh was sitting in New Balance’s Boston headquarters when chief marketing officer Chris Davis swung by his desk and plopped down a magazine. It was a copy of SLAM magazine — the edition with Flagg on the cover celebrating his commitment.

“Go get him,” Davis told Lokesh. “He’s perfect.”

Several apparel companies wanted to sign Cooper Flagg. New Balance won him over. (Courtesy of New Balance)

Lokesh understood the challenge in doing so. Landing Flagg would represent New Balance’s biggest basketball acquisition since 2018, when it signed likely Hall of Famer Kawhi Leonard away from Jordan Brand. That move reignited a basketball line that had been dormant since the 1980s, back when James Worthy was still New Balance’s signature basketball athlete. And while New Balance had complemented Leonard with other top NBA players over the last seven years — including Jamal Murray, Dejounte Murray and Tyrese Maxey — it still looked for another top-line star.

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New Balance’s basketball division saw that person in Flagg. He was someone, depending on how his career broke, who could carry the larger mantle alongside brand’s other worldwide faces: tennis star Coco Gauff, Los Angeles Dodgers pitcher Shohei Ohtani and Arsenal midfielder Bukayo Saka.

From December until May, Lokesh and his team researched what it would take to make the landscape-altering signing. They dove into Flagg’s humble origins and came to appreciate someone who preferred a tight-knit circle over mass exposure. Their priority on keeping jobs in New England aligned with Flagg’s overwhelming support for his home region. Perhaps most importantly, New Balance’s private “boutique” approach meant they could sell Flagg on being a centerpiece rather than just another face in the crowd.

That last piece appealed to Flagg and his family in a major way. In fact, it was one of the deciding reasons they eventually chose New Balance over other apparel companies — including Nike, which sponsored the EYBL grassroots circuit Flagg played and starred in.

“It was just the way that they were willing to believe in Cooper and invest in him early on and say, ‘He’s our guy,’” Kelly Flagg said. “They had a very clear strategic plan of how they were going to implement him into their space, and there was a clear path to him potentially getting his own shoes or his own things — where some of the other companies were playing it maybe a little more safe and saying, ‘You know what, we’ll see how he does,’ and kind of put it on the shelf.”

After the Four Seasons meeting, New Balance was firmly in the driver’s seat to land Flagg, but it still needed to seal the deal. Lokesh wanted to arrange for the entire family to fly to Boston to meet with Davis, someone they’d be working with directly on many of Flagg’s future endeavors. But it was already June 2024, and the Flaggs had scattered: Cooper was on Duke’s campus; his twin brother, Ace, was back in Maine training with former Boston Celtics center Brian Scalabrine; and his parents were in the process of moving to Greensboro, N.C., where they stayed all of last season to be close to both boys. In the days leading up to the Boston meeting, Lokesh overheard Kelly lamenting how she hadn’t seen Ace in a while because of the chaos.

So when Davis eventually booked Cooper’s and his parents’ flights to Beantown, he also scheduled a car service to drive Ace down for the day.

Not for any business reasons. Just to show what New Balance was about.

“We’re not signing Ace, but come on. Your mom’s here,” Lokesh said. “This is how a family brand works.”

There was only one major hiccup in Flagg signing with New Balance. Duke was a Nike school.

Per the university’s Nike agreement — which is standard across college athletics — Flagg would only be allowed to play in Nike apparel during his time in Durham. New Balance could still sign him to a personal, long-term brand deal … but for a year, as Flagg was exploding on the college basketball scene, the company would have to watch him in a rival’s apparel. It was an unforeseen complication in the NIL era, especially amid one of the most lucrative individual apparel deals a college athlete has signed to date.

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No wonder that back in the Four Seasons conference room, one of Kelly’s first questions was, “How would we handle this?”

“We’re in it for the long term,” Lokesh told the Flaggs. “One year of him wearing a direct competitor’s product will not upset us or ruin something we know is great down the road.”

Instead, Duke and New Balance were proactive to work around the situation. Between Duke’s two summer school sessions, for example, Flagg flew home to Maine and shot the advertising campaign New Balance used to announce his signing in August 2024. The company also outfitted Flagg — and his family, which had accrued a healthy amount of rival apparel during Flagg’s grassroots career — in more New Balance gear than they could fit in their closets. Flagg and Duke coach Jon Scheyer even had a “friendly conversation,” in Scheyer’s words, during the preseason about how they’d manage the arrangement.

“If anything, in 2025,” Scheyer said, “the player has the power to do whatever they want.”

Duke is a Nike school, which meant New Balance had to see Cooper Flagg in rival’s apparel for one season. (Jamie Squire / Getty Images)

But Flagg never forced the issue, understanding the terms of the dual contracts he was bound by — although he did still bust Scheyer’s chops a time or two about wanting to wear New Balances in a game.

“I mentioned it a couple of times,” Flagg said, grinning, “but it was always just jokes.”

Lokesh and several other New Balance figureheads were in Durham for Flagg’s first regular-season college game, a blowout win over Maine in which he posted 18 points, seven rebounds, five assists and three steals. But that was one of only two times Lokesh said he saw Flagg between June 2024 and the end of Flagg’s freshman season, which culminated with Duke losing to Houston in the NCAA Final Four. Instead of suffocating its new signee throughout the season, New Balance sent a basic message to Flagg.

“Enjoy college. Don’t feel like you’ve got to go do an appearance at the New Balance store because you’re in North Carolina,” Lokesh explained. “We strategically set out the pitch that said if we do this long-term deal … then we don’t have to worry about one year at Duke.”

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That didn’t prevent New Balance from celebrating Flagg from afar, though. The company posted billboards in various ACC cities celebrating Flagg’s standout campaign, and another round after he was named ACC Player of the Year. Once Duke made it to San Antonio for the Final Four, New Balance made sure to pepper the airport with more promotional materials celebrating the teenager, who by that point had been named the consensus national player of the year.

And now? With Flagg officially in Dallas as the face of the franchise’s future? Now comes the fun stuff.

That began with a draft party this week at Flagg’s hometown high school in Maine, Nokomis Regional, where he won a state championship his freshman season alongside brothers Ace and Hunter. (New Balance is even making Nokomis new basketball uniforms as part of Flagg’s deal.) The brand also worked with Maine’s state legislature to officially declare June 25, the first day of the NBA Draft, as “Flagg Day.”

But what’s next is what everyone, Flagg included, has been waiting for: shoes. During his lone season at Duke, the Blue Devils would open their facility late at night so Flagg could “stress-test” different pairs of New Balances, in anticipation of a limited-edition, player-exclusive colorway set to launch in the lead-up to his Dallas debut. Flagg recently chose the colors and shot a promotional campaign for the shoes back in — of all places — Los Angeles, where he spent most of his pre-draft prep time.

“We’re not gonna do a signature shoe (yet),” Lokesh said, “but we’ll do a small run of stuff that will be accessible to people all around the world: to have a piece of Cooper at this really pivotal moment.”

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That’ll be as welcome for the Flagg family as it is for any of Cooper’s fans.

“Everybody has been crazy bugging us from the state of Maine: When is he going to have something? There’s the Kawhi (shoe); when is the Cooper shoe coming in?” Kelly joked. “I don’t know how many people there are in Maine, but I imagine that they’re gonna sell out pretty quickly.”

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Back when Flagg was a kid, getting a new pair of shoes every summer at the Skowhegan tent sale, he never could have imagined that one day, shoes bearing his favorite colors might be sold at the same place. Now that he’s on the precipice of that reality, it’s only underscored that he and his inner circle made the right choice 13 months ago.

“That was never really a thought, or anything I thought would be reality,” Flagg said. “But definitely going through it now, it’s really cool to just be in the position of seeing how it all works and being given these opportunities.”

(Top photo: Mike Lawrence / NBAE via Getty Images)

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