In 1997, Winsome wrote and produced a root play entitled Ruff Rider, in which family, sexual abuse, love, work, and friendship all intersect. According to author Thomas, author of, "In all of her work, the sympathetic characters are those she portrays as struggling to balance their own pursuit of individual gain with ‘living well together’ with others. As they negotiage the fine lines between egalitarianism and hierarchy, her characters also contribute to the public debate regarding the gendered dimensions of respectability and reputation."[22]