For 25 years, nonprofit administrator and foundation executive, Cleo Wilson served as the Executive Director of the Playboy Foundation, a corporate giving program of Playboy Enterprises, Inc. Wilson engaged the Foundation in the process of “micro philanthropy,”—including many grassroots efforts in Chicago. She continued to fight for civil liberties and racial equality, filing a lawsuit against the City of Chicago and the State of Illinois to ensure fair voting protection for Chicago’s African American residents and serving as vice president of the Illinois Chapter of the American Civil Liberties Union. Wilson was also an early HIV/AIDS activist and was appointed to the Chicago AIDS Foundation’s Board of Directors in 1989. She then served as president of the organization for three years. Before retiring in 2012, she was a founding board member and Executive Director at Intuit: The Center for Intuitive and Outsider Art.