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Shooting for the Stars: UWBG Manager Leaps Between Basketball Court and Community Service

When she was just 7 years old, Molly Caldwell made a promise to her parents: if they would pave that patch of dirt she used as a backyard basketball court in her hometown of Eubank, Ky., she would practice hard enough to earn a scholarship to play college ball.

Molly’s parents agreed, and the young athlete’s hard work paid off. Ten years later, she was awarded a basketball scholarship to Transylvania University in Lexington, where she played not only basketball, but collegiate golf throughout her four years. She graduated with a degree in marketing in 2002.


“I’ve got a big scrapbook filled with stories about my years playing for Pulaski,” said Molly, now Director of Corporate Engagement for United Way of the Bluegrass in Lexington. In high school she played in two Kentucky high school girls championship games, was regional player of the year and a member of the 1,000-point club and is listed eighth on the list of all-

time greatest rebounders and steals.


Into the classroom and back on the court


Molly has since dedicated her life to making an impact both on and off the court. Her first job was a teaching position at Boyle County High School, where she also coached both girls golf and basketball. And though she loved inspiring students in the classroom and on the court, an observation by a female referee one summer at basketball camp changed her life’s course. She praised Molly’s work on the sidelines — but believed she belonged on the court, officiating.

Molly took that advice to heart and decided to try her hand at refereeing. She climbed the ladder, working at AAU tournaments, men’s leagues, and middle school and high school games for the Bluegrass Basketball Association. Eventually she became a familiar face at numerous state tournaments, culminating in 2017 when she was named Official of the Year by the Kentucky High School Athletic Association.


Hitting the big time


From there, Molly began her collegiate journey with the NAIA, where she was selected to officiate at four consecutive NAIA Championships. She was subsequently hired by NCAA Division 1 women’s basketball in 2015. Today, she officiates in 10 Division 1 conferences, and in 2022, was selected for the Women’s NCAA Tournament, with her first assignment at Iowa University.

In order to take on this responsibility in the highest echelons of collegiate sports, Molly needed a career where she could officiate nationwide and still make an impact on her community. In 2008, she joined United Way of the Bluegrass, where she became a development officer, managing giving campaigns and donor relationships. “As a lifelong athlete, I’ve never been one to sit on the bench,” Molly observes.


And as a former coach, Molly says the only thing that was hard in her transition to officiating was her inclination to keep on coaching the girls.


“It was hard for me to leave the students, and I did have to leave off trying to coach them during games. It was hard, but I made peace with it,” she says with a laugh.

State Parks and WayPoint Centers


Molly left UWBG in 2013 to become president of the Kentucky State Parks Foundation. Then, in 2020 sports stepped in, changing her life once more. While on the golf course with a former UWBG donor, Molly learned about UWBG’s WayPoint Initiative and was intrigued. She reached out to a former colleague to learn more, saw the program served a great need — and that it was a cause she could passionately market to UWBG donors.


The WayPoint Initiative is a network of community centers where families and individuals in underserved neighborhoods and communities of color can access a variety of vital services.

“As an official and as part of the UWBG team, I’m able to play an active role in making an impact on the court for female athletes and in the community for my Central Kentucky neighbors,” Molly said. “I’m grateful to have the opportunity to pursue these passions by balancing both careers.”


Blending her job as an official and with the United Way has easy for Molly, who feels strongly about her place as a role model, particularly to young girls in sports. Molly says several years ago she briefly considered a career officiating for the NBA but decided to stay in women’s sports. Even today, women’s collegiate players will marvel when there are three women officiating their games. Molly tells them if they love the game, they don’t have to leave when they graduate — officiating is a career open to women who love the sport. “I always say you have to see it to be it,” she said.

Each UWBG WayPoint Center brings together the region’s most effective nonprofit, government and business organizations to leverage their strengths to tackle our biggest issues. With a system of partners and programs, each aims for the greatest impact on local families from a physical anchor point. Central Kentucky currently is home to three WayPoint Centers, two in Lexington and one in Paris. Two more are slated to open in 2023.


Within months of her joining UWBG, Molly helped secure three large grants to get the first WayPoint Centers up and running. She currently serves as director of corporate engagement, working with business partners and major donors, managing staff and identifying grant funding opportunities.


When she’s not on the basketball court, you can find Molly in Lexington with her fiancée Kaelyn and their son, Jed.

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