Free was born in Red Oak, Oklahoma, and after she graduated from law school she began her legal career with the United States Department of Justice; she was the youngest attorney ever hired by the DOJ. At DOJ, Free prosecuted federal environmental laws across the country with a special emphasis on tribal lands. In 1998, she ran for and became the first woman and the first Native American ever to be elected District Attorney in Southeastern Oklahoma. During her administration, she focused her efforts on fighting for women, children, and crime victim's rights.
Free established the very first political action committee devoted to electing Native American candidates at the local and state level, INDN's List (Indigenous Native Democratic Network). Kalyn has an abiding interest in Japan and has represented the United States on trips to Japan sponsored by the American Council of Young Political Leaders.
Throughout 2011 Ms. Free worked as the attorney and senior adviser of Bill John Baker's campaign for Principal Chief of the Cherokee Nation against the incumbent Chief, Chad "Corn-tassel" Smith. Free again served as senior advisor on Baker's successful re-election in June 2015. Currently, Free represents Baker as his Special Counsel.
Free is also the author of "Why? Rising to the Challenge" in Voices of the Heartland where she describes her career and struggles as a Native American.