Montgomery, born in St. Albans, starred at South Charleston High School, leading the Black Eagles to two state championships (2004, 2005) and winning the Mary Ostrowski Award as West Virginia’s top girls’ basketball player in 2005.

At the University of Connecticut, she helped the Huskies win an undefeated national championship in 2009 and earned the Nancy Lieberman Award as the nation’s top women’s point guard. Selected fourth overall in the 2009 WNBA draft, Montgomery won two WNBA championships with the Minnesota Lynx. After retiring, she became a TV commentator, business owner, and advocate for women’s sports and social justice. In 2021, she became part-owner and vice president of the Atlanta Dream, making her the first former WNBA player to own part of a league team. She also became the first woman to own a team in the Fan Controlled Football league.