Just like the case with another Mav and former Duke player, Dereck Lively, Cooper Flagg’s mom has been key in his development.
“My biggest supporter? Probably my mom. She’s been there every step of the way,” Dallas Mavericks draft pick Cooper Flagg said on draft night.
And Kelly Flagg is not your normal mom. She is a former college basketball player for the Maine Black Bears and a very accomplished one at that. Not only did Kelly Flagg (Bowman at the time) co-captain the team’s first ever NCAA tournament win where they upset Stanford 60-58 in 1999, she also led them to three America East championships.
Kelly Bowman Flagg was a co-captain for @BlackBearsWBB for their first-ever NCAA Tournament win, where they upset Stanford 60-58 in 1999
Her son Cooper Flagg was drafted No. 1 overall in the 2025 @NBA draft tonight.#NCAAWBB x @NBA, @BlackBearNation pic.twitter.com/nMzWZsoBIK
— NCAA March Madness (@MarchMadnessWBB) June 26, 2025
Before that, she was a high school standout in Newport, Maine. Her high school coach, Charlie Wing, described her like this: “She’s a very well-rounded player who does everything well. She also has a tremendous desire to succeed and is very coachable. I wish I had a dozen Kelly Bowmans.”
Sound familiar?
And according to Cooper, he never managed to beat her one-on-one.
Both Cooper’s mom and dad played college basketball, Ralph Flagg for Eastern Maine Community College, so Cooper was born into a basketball family, though it was Kelly who worked with Cooper and his brothers on-court, while she coached her former high school girl’s varsity basketball team.
And Kelly Flagg had a very active hand in developing what will probably be the next American superstar, Cooper Flagg. Actually, a hand is not giving her enough credit, she coached Cooper from being a tall boy in Maine to the biggest story in American basketball.
Cooper is quick to give his mom credit, and the way he speaks about her reveals that she is a big presence in his life and development.
“I still missed a bunch of free throws. I bet my mom probably wasn’t very happy with that,” he said with a smile during the Summer League.
Even more telling about just how important Kelly has been in getting Cooper ready for the biggest stage is this story on why he reclassified to graduate high school in three years and position himself as the youngest number one NBA Draft pick since LeBron James:
“A quote my mom likes to say a lot: ‘If you’re the best player in the gym, then you need to find a new gym.”
This, along with stories about how he manages to stay calm during pressure, like this comment from Kelly Flagg, are signs that Cooper already is a mentally very strong player. That comes with experience and it comes with guidance and is helped along by mentors who have been in similar situations, like Kelly has.
“Very proud of him for drowning out the noise and continuing to get better!” Kelly wrote after a tough game last year.
Photo by Jacob Kupferman/Getty Images
And the difference it makes to have the guidance of a parent, who has been through a lot of big moments themselves, is real. It gives a teenager a big advantage when they have someone at home to talk to about the pressure of the moment and the mentality needed to succeed on the highest level.
Another player, who has been outspoken about how important his own mom’s basketball experience and support has been to his development, is Dallas Maverick center Dereck Lively.
Kathy Drysdale, who tragically passed away from cancer last year, had been Dereck’s coach and rock all through his childhood, Duke tenure, NBA draft and rookie year on the Mavericks. She was a former Division 1 player herself, a standout at Penn State, who went on to work for the Philadelphia 76ers from 1993-2008, while coaching, guiding and supporting her son. Dereck never missed a chance to talk about how important she was to him, and still is. A few months after her passing, he credited his first NBA career threepointer to her.
“It’s for her. She helped me make it, she’s going to help me make a lot more.”
Another example from this year’s draft is Ace Bailey, who was selected fifth overall by the Utah Jazz. He recently talked about how his mom, Ramika Mcgee, who played basketball at West Virginia Mountaineers, was a big part of him getting to the NBA:
“Her giving me advice, giving me goals, what you gotta do, how dedicated, sacrifices and all that. It poured in and it worked and I listened.”
This trend of more and more former competitive basketball players turned mothers taking over as their kids’ coaches, developing and guiding them all the way, is a significant shift. Until recently, it was mostly fathers who coached their kids, especially sons, but as more and more girls and women in the US have and have had access to organized sports, more mothers take on the task, as well. Christine Brennan, who is the author of the new book, On Her Game: Caitlin Clark and the Revolution in Women’s Sports, talked more about that on a Maine radio show earlier this week.
Brennan, who is an award-winning sports columnist, is convinced that this trend is here to stay. In the future, we can look forward to seeing even more excitement around women’s sports, women’s basketball and more women involved in the business surrounding sports – as well as mom coaches, guiding their sons and daughters all the way, like Kelly Flagg, Kathy Drysdale and Ramika Mcgee have done to great success.