Chauncey was born in Oakland CA on October 20, 1949 his father Chauncey Bailey senior and mother Bridgett Marie Dewey-Bailey. He was the second of three children had a younger brother named Stephen bailey and an older sister Lorelei Bailey. He attended Webster Elementary, Bret Harte Junior High and graduated from Hayward High in 1967.
Chauncey was an A student excelling in academics more than sports. However he loved baseball basketball and played as a child with family members and friends on Byron Street in Hayward. Later he played on the softball team with the Oakland Tribune.
His parents nicknamed him “Skippy” due to his stutter although by 18 he had overcome the speech impediment. After high school Chauncey started college at San Jose state. His sister says he was a late bloomer socially but quickly found his passion in communications. During his years in college he wrote for the San Jose Mercury News.
Chauncey majored in journalism and in his spare time wrote creative pieces.
After graduating from San Jose State he went to Chicago to join the newspaper agency the Chicago Tribune. He stayed there three years, where he met his wife Robin Hardin, a local TV personality. Then they moved to Detroit where Chauncey was a reporter for the Detroit Free Press.
Chauncey became a surrogate parent to his niece for ten years and during this time began taking the bus frequently so he could be closer to “the people.” On his first bus ride he noticed people looking out the window, so the next day he began bringing newspapers handing them out to people on the bus. He did this every day for five or six years.
From Detroit Chauncey traveled to DC to work for a 2 year stint with the Associated Press before deciding to return home because of his love for the west coast and Oakland in particular.
He went to work for the Tribune and the Daily Review. He also became the proud father of a son-Chauncey Stephen Bailey.
Chauncey moved to St. Kitts to live for a year after leaving the Tribune. Upon his return he worked at Soul Beat and KDIA and wrote screenplays in his spare time. He secured editorial positions at the Post and the Globe. He was recently in talks with Lions Gate Films, regarding the production of one of his screen plays.