Kelly Flagg doesn’t tell the story with a swagger in her voice or the kind of triumphant pride you’d expect from a mom who can claim to have gone undefeated against a future NBA star. She tells it like someone who cherishes a private little slice of history, knowing that, no matter how many bright lights shine on her son Cooper Flagg in the years to come, she’ll always have this one win—this one streak—that time can’t touch.
It starts the way a lot of basketball stories start in small-town America: in the driveway.
Back when Cooper was just a little kid with a ball nearly too big for his hands, he’d tag along behind his mom, always looking for a game. Kelly, who had been a college player herself at the University of Maine, never needed much convincing. She wasn’t the kind of parent who just sat in a lawn chair with a whistle and a juice box; she played. And when she played, she didn’t go easy.
“We didn’t have a hoop in the house, so we were always outside,” she says, remembering with a laugh. “Even in the winter sometimes. Maine winters. We’d shovel off the driveway and play until our hands were too cold to shoot.”
At first, the games were more about movement than competition. Cooper was young, wild-legged and uncoordinated. He’d chase the ball more than dribble it, shoot rainbow airballs that barely grazed the net, and lose track of the score by the second basket. But the fire was always there. He didn’t just want to play—he wanted to win.
“And I wasn’t going to let him,” Kelly says. “Not just hand it over. Not even when he was nine, ten, eleven. You earn it.”
As Cooper grew, so did his skills. The kid had bounce. His limbs stretched longer each year like some kind of basketball beanstalk, and suddenly those shots started falling. His handle got tighter. He was thinking the game, learning how to read her movements, cut off angles, bait her into mistakes.
But no matter how close it got, Kelly stayed unbeaten.
The family began joking about it. “You still haven’t beat mom,” someone would chime in whenever Cooper came back from a tournament or dropped 30 in a game. “Still 0-fer.” He’d roll his eyes, grumble, and say, “Next time.”
But next time never quite came.
One of those last games, Kelly remembers vividly. Cooper was around 14. Already taller than her, already stronger, faster, playing above the rim while she played below it. He was serious this time—quiet, focused. There were no jokes, no letting up. He wanted this win bad.
It was played in the backyard again, same old rim, same cracks in the concrete they always had to dribble around. No crowd, no cameras. Just the two of them and the occasional gust of wind.
“I got out to a lead, which I think kind of annoyed him,” she says. “He was used to blowing everyone out by then. But I knew how to guard him—he hadn’t really developed a jump shot yet, not a consistent one anyway, and I wasn’t going to let him bully me down low. I had to get creative.”
She smiles as she remembers throwing little fakes, using old-school footwork, leaning into her strength, and pushing back every time he tried to drive.
“He was definitely fouling me,” she says with mock sternness. “But I gave it right back.”
They played up to 11. The score was tied 9-9. Cooper had the ball. Game point. He jabbed left, drove right, got her off balance just enough. Went up strong.
“And I blocked him.”
That part still makes her laugh.
“I don’t even know how. It was like the one time I timed it just perfectly, and I got my hand on it and sent it flying. He just stood there, staring at me like, ‘Did that really just happen?’”
She got the ball back, hit a jumper from the elbow. 10-9. Then, on the next possession, she posted up, spun baseline, and banked it in.
Game over.
“He just kind of dropped to the ground, laying on his back in the driveway, like he’d just lost Game 7 of the Finals.”
She’s laughing now, shaking her head at the memory. “I walked over and stood above him, looked down, and said, ‘Still undefeated.’”
That was the last time they played 1v1.
There were plenty of reasons, most of them practical. Cooper’s schedule blew up soon after that—travel ball, high school phenom buzz, calls from colleges, then the reclassification to the 2024 class, the move to Montverde, the five-star attention. Life sped up. There wasn’t much time for backyard games anymore.
But there’s a part of Kelly—and a part of Cooper, she suspects—that liked leaving it there.
“I think he knows that if we played today, he’d win,” she says. “He’s too good now. It wouldn’t even be close. But we both kind of like that there’s still this little thing. Our thing.”
She pauses for a moment, looking out the window.
“There’s this idea that moms just cheer from the sidelines. But a lot of us—especially moms like me—we played, too. We remember what it’s like to battle, to compete. So when I say I beat Cooper, and that he never beat me 1v1, I mean it. I earned that.”
And she’s proud of the player—and person—he’s become. The wins and awards, the highlights and headlines. But what she remembers just as clearly are those cold driveway days, the scraped knees, the laughter, the trash talk, the grind.
“I always told him—respect the game, respect who came before you. He knows that now. He lives that now.”
Still, every once in a while, she teases him.
“You know,” she’ll say at dinner, “that record’s still intact.”
And Cooper will smile, shake his head, and mutter something under his breath. Maybe one day, they’ll run it back. Maybe not.
But no matter how the rest of his basketball journey plays out—whether he’s the #1 pick in the draft, an All-Star, an MVP, or more—there’s one scoreboard he hasn’t flipped.
Kelly Flagg — undefeated.