In 1942 Howard became chief surgeon at the hospital of the Knights and Daughters of Tabor in the all-black town of Mound Bayou, Mississippi. Within five years, he had founded an insurance company, a hospital, a home construction firm, and a large farm, where he raised cattle, quail, hunting dogs, and cotton. He also built a small zoo and a park as well as Mississippi’s first swimming pool for blacks. In 1947 he broke with the Knights and Daughters, organized the rival United Order of Friendship, and opened the Friendship Clinic.
Howard entered the civil rights limelight in 1951 when he founded the Regional Council of Negro Leadership. One of its officials was Medgar Evers, whom Howard had hired as an agent for his Magnolia Mutual Life Insurance Company. The council mounted a successful boycott against service stations, distributing twenty thousand bumper stickers bearing the slogan, “Don’t Buy Gas Where You Can’t Use the Restroom.”