The third of ten children, Smiley was born September 13, 1964 in Gulfport, Mississippi, the son of Joyce M. and Emory G. Smiley. When he was two his father, an Air Force non-commissioned officer, was transferred to Grissom Air Force Base in Bunker Hill, Indiana. Upon arriving in Indiana, the Smiley family took up residence in a crowded mobile home in Kokomo. Although the family was poor, Smiley observed in the introduction to Hard Left that "while we never had a lot of what we wanted, I can't say we ever went hungry, either." His father often worked several part-time jobs to support his large family, and Smiley wrote of him, "I've never known anyone with a stronger work ethic." Smiley's mother was an associate minister at their church, the New Bethel Tabernacle, part of the Pentecostal Assemblies of the World. Smiley recalled for the Washington Post that he was in church every day when he was growing up.
Acutely aware that Indiana had once been the location of the national headquarters of the Ku Klux Klan, Smiley nevertheless described his youth in Hard Left as "a typical Midwestern small- town life." He was one of only a handful of African American students in an otherwise all-White high school, but he did not allow this to become an obstacle. He was elected class president and voted "most likely to succeed" at his high school. Smiley observed in Hard Left that "although I lived in a nearly all-White community, I never felt 'less than' simply because of the colour of my skin. I learned that people of different races can and do get along.
Smiley's love for politics began at the age of 13, when he attended a campaign speech by then-U.S. Senator Birch Bayh at an American Legion Hall. That night, he abandoned his dream of becoming a major league baseball player when he realized that politicians were in a unique position to motivate people and positively affect their lives. Upon graduation from high school, Smiley attended Indiana University in Bloomington where he landed a spot on the debate team and became active in student government. He also got involved in local politics by working for the mayor of Bloomington, Tomilea Allison. Having achieved "everything I wanted to do in college except graduate" by the end of his junior year, Smiley told the Los Angeles Times that he considered dropping out. However, a friend persuaded him to stay in school and seek work as an intern. After repeated telephone calls and letters to the office of Los Angeles mayor Tom Bradley, Smiley was eventually granted an internship.
After graduating from Indiana University, Smiley worked for three years as an administrative aide in the Bradley camp. At the age of 24, he was the youngest member of Mayor Bradley's executive staff. In 1991, Smiley left Bradley's staff to run for city council in Los Angeles. Running against incumbent Ruth Galanter, Smiley finished a respectable fourth in a field of 15 ...