Upon graduation, Wiley earned a position at the Oakland Tribune, where he coined the famous phrase "Billyball" to describe the managerial style of Billy Martin. He quickly climbed up the ranks from copyboy to beat writer and eventually became a regular columnist. In 1982, he was hired by Sports Illustrated, where he wrote 28 cover stories over a nine-year period, mainly about boxing, football, and baseball.
Wiley published several books during the course of his career, including Serenity, A Boxing Memoir; Why Black People Tend To Shout; and By Any Means Necessary: The Trials and Tribulations of Making Malcolm X, with Spike Lee.
Additionally, Wiley wrote articles for GQ, Premiere, and National Geographic. He was a weekly contributor to espn.com's Page 2, where he wrote more than 240 columns. His presence on TV included ESPN's The Sports Reporters and regular guest appearances on SportsCenter.
In skirting the line between sports journalism and literary fiction, Wiley wrote many Page 2 articles in the third person, featuring discursive, jazz-inflected prose and dialogue conducted between himself and a fictionalized character whose identity the writer left deliberately obscure.
Wiley died of a heart attack on June 13, 2004 while watching Game 4 of the 2004 NBA Finals. Survivors included his companion, Susan Peacock of Orlando; his mother, Dorothy Brown of Washington; a son from his marriage to Holly Cypress, Colen C. "Cole" Wiley; a daughter from his marriage to Monica Valdiviez, Magdalena Valdiviez-Wiley; and a half brother, Samuel Graham of Memphis.
- Tributes to Ralph Wiley at ESPN.com
- "Freedom Rider, Ralph Wiley" by Margaret Kimberly
- "Sportswriter Ralph Wiley Dies; Essays Probed Black Life" The Washington Post, June 16, 2004; Page B06