Legg served three prison sentences for drug possession (two in Arkansas and one in Oklahoma) before attending classes with the Cherokee Nation re-entry program, which assists formerly incarcerated Cherokee Nation citizens with finding jobs, housing, and school after release.
[1] From 2013 to 2019, Legg worked as the Cherokee Nation's Career Services Coming Home Re-entry Program director.
[2] In 2014, he was named a "Champion of Change" by the Obama administration for going from being sentenced three times for drug possession, to running a re-entry program for Native Americans.
[3] Legg ran for the Cherokee Nation's 6th district seat being vacated by Bryan Warner in 2019; he faced Ron Goff and Gary Trad Lattimore in the general election.
[6] Legg said of his election to the tribal council "I feel like I carry a big torch for those that are also convicted felons.