Dailey grew up in Youngstown, Ohio, with parents John and Rose-Marie (Genetta) Dailey and two sisters, Kathleen and Colleen. After graduating from Ursuline High School, he pursued a career in law enforcement at Youngstown State University before becoming a crime reporter for various stations in Ohio, including WNIO 1540-AM and ABC affiliate WYTV. He later worked as a radio host at CKLW in Windsor, Ontario, and then moved to Toronto where he joined Citytv. During his time at Citytv, Dailey became known for his famous line "This is Citytv, everywhere". Despite surviving prostate cancer, Dailey was eventually diagnosed with kidney cancer which spread to his lungs and resulted in his death on December 6, 2010 at the age of 57.