[8] Winegardner's debut novel The Veracruz Blues was published in 1996, and centred on five brother's attempt to create a Mexican baseball league that could rival the MLB.
[11][12] The book is set in midcentury Cleveland, Ohio and centers on the relationship between David Zielinsky, an engaged man from a union family, and affluent journalist Anne O'Connor.
[14][15] Winegardner was chosen by Random House to write a sequel to Mario Puzo's novels The Godfather and The Sicilian after the author's death in 1999.
[16] It received mixed to positive reviews from critics, with Sarah Vowell of The New York Times calling it "a fine, swirling epic.
[20][21] Winegardner has won grants, fellowships and residencies from the Ohio Arts Council, the Lilly Endowment, the Ragdale Foundation, the Sewanee Writers Conference and the Corporation of Yaddo.
His work has appeared in GQ, Playboy, Ploughshares, TriQuarterly, Doubletake, Family Circle, The Sporting News, Witness, Story Quarterly, American Short Fiction, Ladies' Home Journal, Parents and The New York Times Magazine.