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Baxter Holmes
ON THE AFTERNOON of May 12, Cooper Flagg’s immediate family gathered inside his hotel room at the Marriott Marquis in downtown Chicago. There was his twin brother, Ace (who is one minute older), his father, Ralph, and his mother, Kelly.
They finished getting dressed for the 2025 NBA draft lottery, which began later that night at 7 p.m. local time at the McCormick Place Convention Center, a short walk from their hotel.
But before heading out together, the family of the Duke superstar freshman, and the presumed No. 1 overall pick in Wednesday’s NBA draft, spent 30 minutes chatting about his future.
They had held these discussions before, weighing all the likely landing spots and what each one presented, but this would serve as a final debrief before one of the most heralded American prospects in years would, later that night, finally know where he’d likely begin his NBA career.
The family had known for months that the Washington Wizards, Utah Jazz and Charlotte Hornets held the highest chances of landing the top pick, and inside the room, they again went over positives about each one.
Washington was a short flight from Maine and North Carolina — the two states where the family split their time. Charlotte offered the same, plus it had a built-in fan base for Duke alums, they said. And Utah was helmed by Jazz CEO Danny Ainge, who played for the 1980s Boston Celtics teams that Cooper’s parents admired so much and introduced their sons to at a young age.
They also weighed a singular, unsolvable negative. Like so many top prospects, Flagg had never endured sustained losing at any level, and almost regardless of his rookie-year performance, he was almost certainly about to do so. And though he long maintained that he “just wanted to hoop” anywhere, those around him say they harbored concerns about how the ultra-competitive prospect would adjust emotionally to such a dynamic.
“It would be hard for me to imagine Cooper going through a season with a lot of losing,” Duke coach Jon Scheyer told ESPN.
Flagg’s father admitted as much. “It was something we talked about,” he said.
A short time later, the family walked to the convention center, and Flagg’s representation offered guidance: The cameras would be on them throughout the night, and especially as the lottery order was being announced, and any reaction — good or bad — would lead to headlines. It was best, they told Flagg and his family, to stay neutral.
Flagg sat in a front-row seat, next to his Duke teammate, Kon Knueppel. Ralph, Kelly, Ace and Flagg’s longtime trainer Matt MacKenzie sat in the row just behind Cooper. Facing the stage, they all watched NBA deputy commissioner Mark Tatum rapid-fire announce the first 10 picks in 2 minutes and 15 seconds. But even that brief window of time was filled with stunners.
Washington and Utah had fallen out of the top four, while the Dallas Mavericks and San Antonio Spurs had leapt into it.
Sitting in their seats, the family tried to maintain their composure, while considering the new possibilities unfolding.
Flagg had imagined, even briefly, a possible pairing with 7-foot-5 Victor Wembanyamathe Spurs’ top pick in the 2023 draft.
Then, Tatum announced the next pick: Charlotte. That meant Dallas, San Antonio and the Philadelphia 76ers were in the top three. The odds of that being the case were, according to ESPN Research, just 1%.
Then, 12 seconds later, Tatum announced that the 76ers would pick third, and the Spurs would pick second, which meant the Mavericks, who entered the night with a 1.8% chance of winning the lottery, had won.
The Mavericks had the fourth-lowest odds to win the lottery since 1985; they jumped 10 spots, the biggest by any team since the NBA changed the draft lottery format in 2019.
IN ONLY A FEW minutes, the Flagg family’s entire calculus, what they had, for months, been outlining and planning for, changed.
The announcement sent shockwaves across the NBA. A franchise — and a fan base — still recovering from the devastating midseason trade of superstar Luka Doncic was now positioned to draft another generational talent in Flagg.
From their seats, Flagg’s family was just as stunned.
“Dallas wasn’t even on our bingo card,” his father, Ralph, said.
Text messages poured in. Were they happy? Sad? Why weren’t they reacting? Did they realize what had just happened?
Their minds raced.
Instead of the pressure of being one of the best players on a losing team, he’d be on one that, just a year ago, went to the NBA Finals. He would be, by any narrative or measure, the man to heal the wounds left by the departure of Doncic, who by 25 had earned five All-Star appearances and been named first-team All-NBA five times.
Flagg immediately would face a different pressure, one few No. 1 picks have experienced: to help a pair of All-Stars, in point Kyrie Irving and forward Anthony Daviswin in the NBA — and fast.
“We never even considered that the impossible could happen on May 12,” one Mavericks team source said. “I’m not sure there has ever been a more abrupt reversal of fortune.”
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JON SCHEYER, WHO coached Flagg for one season at Duke, watched from his hotel in Amelia Island in Florida, where the ACC spring meetings were being held.
“To me, it’s a dream spot,” Scheyer said of the Mavericks. “I really feel that way.”
And as Flagg and his family walked out of the convention center that night, they began to feel the same.
Two Duke players were already on the roster, Irving and center Dereck Lively IIa first-round pick in the 2023 draft. Scheyer told Flagg soon after that center Khaman maluach and Lively were two of the best people he had coached. Flagg had played alongside Maluach during his freshman season with Duke; now he’d likely play alongside Lively during his first season in the NBA in Dallas. “Enjoy that!” Scheyer told him.
Flagg could learn from players who had won championships, they thought, such as Irving, Davis and, they hoped, retired Dallas legend Dirk Nowitzki.
“He’s not going to go into Dallas thinking he’s got all the answers,” Scheyer said. “He’s going to learn from Kyrie, he’s going to learn from [Davis]. He’s going to learn from Derek Lively and Jason Kidd and his staff. He’s coming in to learn, and I think that’s a special part about him.”
Like so many, the Flagg family had monitored the voluminous backlash from Mavericks fans after Doncic was traded abruptly to the Los Angeles Lakers last season. The Flaggs saw the jersey burnings, the mock funerals, the protests.
To them, though, it represented strength — an admirable bond with the organization, even if it had been badly strained.
“They are a very passionate fan base,” Ralph said, “and I think from what we understand and what we’ve seen on social media, they’re ready to fully embrace Cooper.”
“Dallas has been lucky for many years,” Scheyer said. “They’ve been able to watch Dirk, Luka — so many winning teams. Now, you’ve got a guy in Cooper, who I think will carry that tradition forward.”
His impact on the organization was felt immediately, first on the team’s bottom line.
“We surprisingly renewed 75-80% of our season tickets,” one Mavericks team source said. “But we had a lot of work to do in earning back the confidence and fandom of a not insignificant segment of our fan base.
“We sold $8 million in new season tickets in the three days after the lottery.”
After the backlash from the Doncic trade, one company that was considering a sponsorship partnership with the Mavericks paused, the source said. Then, after seeing the lottery and the positive fan reaction, that same company agreed on a new sponsorship deal with the team.
“We have done two additional new sponsor deals, one the second largest in our history, since the luck of the lottery,” the Mavericks source said.
After the lottery, Flagg bounced across the country, working out with MacKenzie at a gym in Westlake Village, about an hour west of Los Angeles. Flagg traveled to North Carolina to see his brother graduate from high school, and then north to Maine to see his former classmates at Nokomis graduate from high school.
The Flagg family already has an Airbnb booked in Las Vegas to watch him during summer league. And while draft parties are being organized in Flagg’s hometown of Newport, Maine, the family has enjoyed a brief solace from the noise and focus of television cameras in Westlake Village, where Flagg continued to work out before heading back to New York for the draft.
Recently, the family visited a Hugo Boss store in Los Angeles for Flagg to be fitted for a suit on draft night. As they watched while specialists worked with Flagg, the gravity of the moment — and what was coming next, the start of his NBA journey — settled in for those around him. They all looked at each other and couldn’t believe how fast everything had flown by.
“He’s in a good place mentally,” MacKenzie said. “He’s in a good place physically, and I think that he’s ready for this next chapter of his career.”
