As a civil rights activist, Ruby Hurley showcased her progressive thinking while with the National Association for the Advancement of Colored People (NAACP). We call her progressive thought "radical" because women, especially black women during the forties and fifties, were encouraged to govern themselves according to societal standards that made them invisible. Hurley served as both the National Youth Coordinator (1943-1951) and Director of the Southeast Region (1951-1978) for the NAACP. Through archival research and summative content analysis, we selected seven sources that show her radical disposition through her writings; letters showing her standing up for her opinions; and her courage in doing undercover work, etc. Using Katie G. Cannon’s essay “Hitting a Straight Lick with a Crooked Stick: the Womanist Dilemma in the Development of Black Liberation Ethic,” we explore Cannon’s assertion that moving toward both a black and womanist liberation ethic requires the ability “to debunk, unmask, and disentangle the historically conditioned value judgments and power relations that undergird the particularities of race, sex, and class oppression.” Our aim is to show how effective Ruby Hurley was as a progressive woman leader and to show how her disposition gave her radical agency within a black and male-centered organization.