Charles Fleming entered the legal profession at a time when Cleveland’s major law firms would not hire black attorneys. However, his outstanding litigation skills became widely recognized when, as an assistant county prosecutor in the 1960s, he was among those assigned by then County Prosecutor John T. Corrigan to handle the most difficult high-profile cases. Fleming gained litigation experience while defending local civil rights activists—often black nationalists—in front of all-white juries. He was a senior partner at the firm of Fleming, Hubbard, and Davis from 1968-1976. Fleming was elected Cleveland Municipal Court Judge in 1976 and served on the court for 19 years, including acting as Presiding and Administrative Judge from 1981-1984.