While Leonard has always featured strong, independent women characters, his writings truly began to reflect the changing role of women in his 1980 novel Gold Coast. But Leonard was still tentative and consequently his protagonist Karen DiCilia is not defined sharply enough for most readers to realize her potential.

Leonard was more successful with Carmen Colson in his 1989 novel Killshot (see separate entry), she is a rounder, more fully developed character than Karen DiCilia. Jackie Burke in his 1992 novel Rum Punch is also richly developed. Still, Karen Sisco is Leonard's most finely detailed portrait of contemporary women.