In his profile on the African American Literature Book Club website, Shepard notes that "As a fifth-grader in Nebraska, I was one of the few Black students in the class, and when American slavery was taught I was embarrassed by the topic." He has sought to present the history of slavery and race in America in such a manner that "young people of color ... (would) not feel the shame, guilt and embarrassment that he felt as a kid while being taught about black history." His first novel for younger readers, Sneakers (1973) was a Council on Interracial Books for Children award winner. His second book Conjure Tales retold African-American short stories that were published in 1890 by Charles W. Chestnutt, a writer of mixed racial heritage recognized as an innovator in addressing complex issues of racial identity in work deeply informed by both literary and folk traditions.
Shepard's book Now or Never!: 54th Massachusetts Infantry's War to End Slavery, (2017) is a work of creative nonfiction that retells the story of the so-called "Glory" regiment of black soldiers in the Civil War. He notes that for many years, on his way to work as an editor at Houghton-Mifflin in Boston, he each day passed Augustus Saint-Gauden's memorial to Robert Gould Shaw, the regiment's white commander, and looking on the features of the black soldiers portrayed there helped inspire him to want to re-tell the great story of their fight against slavery from their own point of view.
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