Kelly Flagg is driving to Cross Insurance Arena in Portland, Maine, on an early January afternoon. In a few hours, thousands of people will line up to catch a glimpse of her son Cooper, who is the most intriguing American basketball prospect to come along in years. He’s just 17, but there will be autographs for him to sign and fans and reporters to meet, eyes and cameras tracking his every move, both on the court and off.
It’s a homecoming for the Flaggs, who have relocated to the Orlando area while Cooper and his twin brother, Ace — also a college prospect — hone their talents at Montverde Academy, a basketball powerhouse. The game this day has been the talk of the Maine basketball community for months.
Kelly Flagg has a lot on her mind: the logistics of the event, fielding requests for her family’s time, giving fellow Mainers an occasion to remember. But when I ask her about raising Cooper and Ace in the small, central Maine town of Newport (pop. 3,200), with her husband, Ralph, her mind turns to an unexpected subject: the 1985-86 Celtics.
Flagg chuckles, recalling the depth of her family’s Celtics fandom. Her family would tune into both the television and radio broadcasts for Celtics games, then turn down the TV so they could listen to Johnny Most call play-by-play. Kelly’s mom hung a full-size Larry Bird poster in the kitchen.
“In fifth grade, I had a Danny Ainge figurine,” Flagg recalls, referring to the Celtics guard who became the team’s president of basketball operations. “Every day of fifth grade, Danny Ainge was in my desk. And when I got to school in the morning, I would take him out and he would sit on the right corner of my desk for the day.”
Decades later, when Cooper began showing an uncommon aptitude for basketball as a second-grader, Kelly knew exactly how to communicate her ideal for how the game should be played. On longer trips in their van to one practice or another, she would pop in a highlight DVD of those 1985-86 Celtics for the boys to watch. “At first, she had to make us [watch],” recalls Cooper, “but then it just became kind of standard in our car. That’s the team everybody in Boston, for sure — everybody in New England — is going to say is their favorite of all time.”
In the years since absorbing those lessons from Bird, Robert Parish, Kevin McHale, et. al, Cooper Flagg has rocketed to an almost unfathomable stratosphere of basketball. After leading Maine’s Nokomis Regional High School to its first Class A Boys State Championship in 2022 as a 15-year-old freshman, he was invited to participate in the USA Basketball Men’s Junior National Team minicamp, despite being two years younger than most of the other players.
By the end of that summer, Flagg had led the US team to a gold medal at the FIBA U17 World Cup. At year’s end, he became the youngest ever to be named USA Basketball’s Male Athlete of the Year.
“It’s ludicrous to think someone can improve as much as he has, but he has,” says Andy Bedard, who coaches the Flagg twins on the Maine United AAU team. Bedard, a former star at the University of Maine, is himself one of the best players the state has ever produced. (Kelly Flagg, who was a standout high school and college player, is also a coach.)
“It’s fun to have [Cooper] on your team because you don’t know if he’s going to get 40 [points]. You don’t know if he’s going to get 28 rebounds,” Bedard says. “It’s like a menu at a great restaurant that changes constantly. You know it’s going to be great, but you don’t know how.”
Earl Anderson, Flagg’s coach at Nokomis, offers a similar evaluation, in a tone that’s part pride, part mystification. “I can go back quite a ways, and there are only a few players I can think of that make every other player on the floor playing with them better,” he says. He mentions Magic Johnson and Larry Bird. Then he says: “Cooper has that knack, that ability.”
It is suggested that maybe it’s a product of Kelly Flagg introducing him to those ‘86 Celtics tapes in the car.
“That’s got to be part of it,” Anderson says with a laugh. “You may be right.”
With his meteoric rise, Cooper Flagg has the attention of the basketball world. Over the summer, LeBron James caused a social-media stir by taking him aside at Peach Jam, the country’s most prestigious AAU tournament, to offer some private words, and Steph Curry and Jayson Tatum both hosted Flagg at their camps. In October, Flagg made the announcement — on the cover of Slam, the national basketball magazine, no less — that he was taking his talents to Duke University.
That’s where Jayson Tatum played in 2016-17, before the Celtics selected him with the No. 3 overall pick in the NBA Draft. “He’s probably ahead of me [at this age],” Tatum says of Flagg. “I wasn’t nearly as athletic when I got into college. It took me a little bit longer.” Seeing Flagg play at camp, Tatum was impressed by his size and skill, but another quality made the biggest impression. “I just like how he had an edge about him, a toughness,” Tatum says. “He was going at guys and trying to go at the best players and trying to block shots. I just loved how he competed.”
While the Flagg family was raised on Boston, they were raised in Maine. The state is passionate about basketball — if you ever wondered what a ghost town looks like, swing by when a high school basketball team has a state tournament game in Augusta, Bangor, or Portland.
The state has produced a handful of college stars and it seems like longtime college basketball analyst Jeff Goodman has seen them all. There’s Nik Caner-Medley, of Portland’s Deering High School, who scored 1,593 points at Maryland from 2002-2006. And there’s Cindy Blodgett, a teammate of Kelly Flagg’s for three seasons at the University of Maine, who scored 3,005 points for the school. Goodman used to say the best Maine player he’d ever seen was Brunswick guard Ralph Mims, who averaged 5.9 points a game for Florida State from 2004-2008 and embarked on a pro career overseas. But then he saw Cooper Flagg. And in 20-plus years of scouting high school players, Goodman says, no one else even comes close.
Flagg’s rise has been accompanied by two recurring questions: How good is he really? And, How did this happen?
The first answer is still being determined, of course, considering he turned 17 years old in December and will not play his first minute of college basketball for months yet. The conjuring of names like Larry Bird and Magic Johnson will perk up any basketball fan’s ears, but the 6-foot-9-inch Flagg’s skill set is more comparable to another Celtics champion, Kevin Garnett (whom Flagg himself has cited as an influence). Like a young Garnett, he plays with an endless reservoir of energy on both ends of the court.
The answer to that second question begins in the town of Newport.
Ralph Flagg and his future wife, Kelly Bowman, both attended Nokomis Regional High School, as would their twins and older son, Hunter. Ralph would go on to play at Eastern Maine Community College. Kelly, who scored 1,257 points at Nokomis, started for the University of Maine when, in her senior season, it upset perennial national power Stanford in the 1998-99 NCAA tournament. (Today, Ralph tends to be content to stay in the background, at least as much as he can at 6 feet 9 inches; Kelly is 5 foot 10.)
Kelly introduced her boys to the sport she and Ralph loved before they were even out of their cribs, giving them a basketball-shaped rattle. Cooper took to basketball first; by second grade, he was playing in a recreational league against fourth-graders. But it wouldn’t take Ace long to fall for the game himself.
When the twins were in third grade, Kelly reconnected with fellow University of Maine alum Bedard, who was putting together a traveling youth team — commonly known as an AAU team — in Southern Maine. Bedard still recalls visiting a gym to see Cooper play for the first time. “You know the dynamic of youth basketball,” he says. “You’ve got some pretty good athletes, you’ve got some kids who are tripping over half-court, you’ve got kids at all sorts of skill levels. And then all of a sudden I saw this kid walking to the end of the line and I thought, [snaps his fingers] That’s Cooper right there.”
The Flagg boys hit it off with Bedard’s son Kaden (who also plays at Montverde, on one of its lower-profile teams), and the family made the commitment to drive the hour-and-a-half from Newport to Portland — with the requisite Larry Bird Film Festival on loop — two nights per week to practice with the AAU team.
“I was a teacher, and as soon as school got out, I ran out of the building, grabbed the kids, we jumped in the car, ordered a pizza from Pizza Hut or wherever, picked it up along the way, and they ate on the way down because everything was going be closed on the way back,” Kelly says. “We would get back about 9 o’clock, 9:30. You’re talking [about] 10-year-old kids. Those were some late nights.”
“It was a lot,’’ acknowledges Cooper. “But at the end of the day it was just kind of a sacrifice we had to make given the opportunity that we were looking at.”
When I suggest to Kelly that her own basketball experiences must have helped her navigate the path for Cooper, she demurs. “I’m glad it seems that way. But to be honest, I had no idea what we were doing and I think a lot of it was luck and then learning along the way.”
“Kelly is the perfect basketball mom,” says Brian Scalabrine, the former Celtic and current NBC Sports Boston broadcaster, who has worked with Cooper since he was at Nokomis. “When I ran [a pickup game in Boston], she was all over Cooper for dribbling too much. She’s all about making the right play.”
While the twins’ personalities are markedly different — Ace is more gregarious; Cooper projects an almost subdued confidence — they share a relentless drive. Whether it’s basketball, fishing, Ping-Pong, or cornhole, the Flagg boys are locked in constant competition. Everyone seems to agree this comes from their mother, which I believe. At one point she notes Cooper has never beaten her one-on-one in basketball. Sure, they last played when he was in fifth grade, and the game ended early when she injured her knee — but still, he never beat her.
“There’s always some sort of competition,” says Bedard, who has also moved to Florida so his son can attend Montverde. “And when [Cooper] loses, he gets pissy, and he wants to play again.”
Montverde coach Kevin Boyle says there’s been one fight on the team this year: Cooper vs. Ace, naturally. (“Cooper took Ace’s toy. Ace took Cooper’s toy back,” is how teammate Liam McNeeley jokingly describes it, clearly familiar with the brothers’ dynamic.)
Such competitiveness benefited their AAU team, the core of which was assembled when the twins were in fourth grade. By the time they were in fifth, says Bedard, they needed to cross into Massachusetts to play in more competitive tournaments, even against sixth- and seventh-graders. “We wouldn’t win every tournament, but it was our little boys playing against kids that have friggin’ beards,” Bedard says with a chuckle. “But we were competing, and that was so much better for them than smacking someone by 30 and holding up a trophy for Facebook.”
Cooper Flagg threw down his first dunk as a seventh-grader, and perhaps not coincidentally, that was when he and his Maine team began receiving bigger opportunities. The team, now called Maine United, was offered a chance to play in the invitation-only Made Hoops East Coast circuit, which featured elite middle school teams from Toronto to Miami. “Not only did [Cooper] play in our East Coast circuit . . . he actually played in our spring circuit, which is like our Midwest and South circuit,” says Eric Hampford, Made Hoops’s director of scouting. “And he dominated there, too.”
While Cooper and Ace made a splash in AAU, the Flagg family looked forward to when the twins would join their older brother, Hunter, on varsity at Nokomis. By the time they arrived as freshmen for the 2021-22 season, Hunter was a senior, and the team had endured some lean times, including going 3-15 the previous year.
His siblings changed that immediately. “That was something that me and Ace and Hunter had always talked about growing up, that we would be able to spend that one year of high school together,” says Cooper. “So we always kind of looked forward to that one year and we always had it circled.”
Over the season, Cooper averaged 20.5 points, 10 rebounds, 6.2 assists, 3.7 steals, and 3.7 blocks per game while leading Nokomis to a 21-1 record and a state title. He was named Maine’s Gatorade Player of the Year.
As dominant as Flagg was at Nokomis — his teammates good-naturedly took to calling him “Hollywood” because of the burgeoning media attention — it was difficult to gauge the depths of his talent. Maine high school referees are notoriously conservative, with dunks sometimes resulting in a technical foul if players hang on the rim for even a fraction of a second.
Bedard puts it more bluntly: “Playing at Nokomis was basically like having a thoroughbred horse running around a baseball diamond . . . He was the Gatorade player of the year, but we didn’t get the full Cooper Flagg. His wings were kind of clipped by the parameters of Maine basketball.”
So after one season and one championship, and with Hunter graduating, it was time to step onto a bigger stage.
Great players can make a basketball gym roar. It takes a truly special player to make one fall silent.
Brian Scalabrine won’t forget when Cooper Flagg did that, after he invited him to one of the high-level pickup games Scalabrine organizes and plays in in Boston. Scalabrine had never met the Flaggs, but had heard the raves about Cooper — he wasn’t sure how seriously to take them, but any doubt didn’t last long.
“Very first possession, he drives right, kind of gets stuck,” Scalabrine recalls. “He pump fakes, the defender kind of gets out of position. He throws it up with his right hand, 1-2 steps, puts his elbow above the rim, and he dunks it with his left hand off the glass.” The whole gym went quiet. “Normally you would be like, ‘Oh, [expletive]!’” Scalabrine continues. “But you could hear a pin drop in there.”
The impression Flagg made was emblematic of his rapid rise to national prominence. After the championship at Nokomis, he has sustained his dominance no matter the competition, challenge, or venue.
The weeks and months after winning the state title in March 2022 have been a whirlwind for the Flaggs. Later that month, to little surprise, the family announced that Cooper and Ace would head to Montverde, which plays a national schedule similar to a Division 1 college program, for their sophomore high-school seasons.
That same hectic March, Maine United was invited to play in the Nike-sponsored Elite Youth Basketball League, perhaps the premier AAU and travel circuits in the country for players 17 and under.
Meanwhile, Cooper Flagg received an opportunity not just to represent his state, but potentially his country. He was among 48 players to be invited to the USA Basketball Men’s Junior National Team three-day minicamp in New Orleans. Flagg, the youngest player invited, got the call in part because of a recommendation Scalabrine had made to his contacts at USA Basketball. “They were kind of like, ‘Yeah, we’ll invite him, but he’s probably not going to make this team. He’s 15,’” Scalabrine says.
Flagg didn’t just make the team, he emerged as its best player. During the championship game of the world cup in Malaga, Spain, he compiled 10 points, 17 rebounds, 8 steals, and 4 blocked shots, beating Spain’s team 79-67. “Barcelona was offering Cooper a contract to come play right now,” Scalabrine says.
By the end of Flagg’s sophomore season, he was considered a top-three prospect in his class. By the end of the following summer, he was considered one of the finest prospects to come along in years.
Flagg became a sensation this past summer with an otherworldly performance at Peach Jam, where he led Maine United to the final of the U16 division. With every pro and college scout worth his or her clipboard in attendance, Flagg averaged 25.4 points, 13 rebounds, 6.8 blocks, and 5.7 assists.
“Last summer, he dominated every single game,” says Jeff Goodman, the basketball analyst. “It was him and [Brockton native] AJ Dybantsa, those two were the best two players at the Peach Jam. They were the two. You could have the number one pick in successive years coming from New England. Like, how ridiculous is that?” Flagg and Dybantsa, who is now part of the class of 2025, squared off this month at the Spalding Hoophall Classic in Springfield, with Montverde edging out Dybantsa’s Prolific Prep, 76-71.
In August, after his summer of extraordinary heights, Flagg reclassified to the class of ‘24, essentially skipping a year of high school to expedite his path to college and the NBA.
“In some ways it was losing a year of his childhood, which is tough, but a lot has happened,” Kelly says. “[T]here’s been a lot of sort of stressful moments, but the stress that we have endured is nothing compared to what other people go through. It’s all good stress.”
After a period of recruiting courtship that included a visit to the University of Connecticut, Cooper chose Duke. The choice was no surprise — he had already referred to it as his dream school, and it was Kelly’s favorite college team.
Duke, which has won five men’s basketball national championships, is arguably the most prestigious program in the country. Current NBA stars such as Tatum, Orlando’s Paolo Banchero, Dallas’s Kyrie Irving, and New Orleans’s Zion Williamson and Brandon Ingram each spent a year there before making the jump to the pros.
Tatum was happy to hear when Flagg announced he was heading to Duke. “Special kid, special player, and he’s going to a special place,” he says. “He’s still a teenager, and there’s a lot you have to deal with and learn. But that’s essentially why you go to Duke. You get to play on the biggest stage.
“There will be a lot of great days and some bad days, but ultimately that’s the best place to prepare you to get to that next level.”
Outside Cross Insurance Arena in Portland, after the Flaggs have found their way inside, a line winds around the building; the crowd is dotted with blue-and-white Duke jerseys, some with “Flagg” stitched on the back.
Inside, there’s a palpable buzz as Montverde prepares to play its first of two games in Portland against highly-ranked teams, a competition billed as — what else? — the Maine Event. There are tables selling “In Flagg We Trust” T-shirts, with $10 from each sale going to the Ronald McDonald House. (At the end of the night, the charity will have $4,000 coming its way.) Tickets for the games sold out in about 12 hours.
The event came together when Made Hoops chief executive Chad Babel suggested the Maine games to Montverde coach Kevin Boyle and the Flaggs, who all quickly agreed. Kelly Flagg played a crucial role in the logistics, such as finding venues.
The games are the Flaggs’ gift to Maine — and they’re a homecoming, but also a send-off of sorts. Kelly notes that this is probably the last opportunity for Mainers to see Cooper play in his home state for a long time, given that Duke doesn’t have a game scheduled here in the near future and the NBA is unlikely to expand to Cross Insurance Arena anytime soon.
While Nokomis fans may have had visions of four high school championships, common sense suggested it was necessary for Cooper and Ace — who has several Division 1 offers and is coveted by UMaine — to leave the state to maximize their opportunities. But these games in Portland should send a clear message: Leaving Maine did not mean they left Maine behind.
Before Montverde’s matchup against the night’s opponent, Gonzaga College High School, the public address announcer introduces Ace as “the pride of Newport, Maine.” The cheers for Cooper drown out his introduction, and if any fans had sat down for the start of the game, he lifts them immediately back to their feet, taking a pass from teammate Liam McNeeley — one of six Montverde players ranked among the top 50 in the country — and delivering a rim-rattling dunk on the game’s first possession.
From the press box high above the court, I scribble my impressions in my notepad: It’s all true. All of it. Plays way above the rim. Relentless on defense. Every opposing shooter is thinking about him even if he isn’t near. Selfless, excellent passer. Shot needs some polish, but by all accounts has come a long way. He’s going to be the best player on winning teams.
Cooper finishes with 23 points, 10 rebounds, 8 blocked shots, and 5 assists in Montverde’s 91-53 win. If there were any skeptics in the building, they had to have been converted to true believers.
After the game, the twins are clearly thrilled that they gave their home state fans a show. “As we’ve grown and our lives have changed, we don’t see home pretty much at all anymore,” Cooper says. “It means everything to come back, see everybody and really feel the support in real time.”
During a packed press conference, a reporter asks him, “How many people do you have here?”
He ponders for a second. “About 7,000?”
The reporter clarifies the question. He means how many family and friends, not the total attendance.
“About 7,000,” interjects Boyle, Montverde’s coach, without skipping a beat.
The next day, at the Portland Expo, Flagg puts on another show, posting 29 points, 9 rebounds, 2 steals, and 2 blocks — and a collection of thunderous dunks — in a win over CATS Academy Boston. When he checks out of the game with a little over 3 minutes left, some in the crowd begin to disperse, trying to get a head start on a looming snowstorm.
But many stay, even after the final buzzer. Around 70 or so people, many wearing Duke gear, mill about the edge of the court, waiting for Cooper and Ace to emerge. Some kids hold pens, hoping for an autograph. Some adults do, too.
At last, the twins emerge. They hug Kelly and Ralph and their friends and family. Cooper heads to the middle of the court, while Ace chats with a smaller group off to the side. For nearly a half hour, they quietly oblige everyone, until it’s time to go. Cooper signs one more autograph for a man in a Tacko Fall Celtics jersey, before disappearing down a stairwell.
From here, the Flaggs are heading back to Florida, home for now. Kelly says that not all of their possessions came south with them. But those old Celtics DVDs? They’re still with them, in their Chevy Suburban. “And I still have my Danny Ainge figurine,” she notes. “Cooper had possession of him for a while and he actually just made the journey [to Florida].”
It’s probably best that the totem is back with her. Cooper is on the cusp of his own journey now. He probably won’t be back home to Maine anytime soon, at least to play basketball. But an entire state cannot wait to see all the places he’ll go from here.