A Daytona Beach, Florida (USA) native, Cherry is a graduate of Morehouse College (B.A., Journalism with honors, 1978). For two years, starting as a sophomore intern, Cherry wrote and produced the 6 p.m. and 11 p.m. weekend sportscasts for WAGA-TV 5, then Atlanta’s CBS affiliate.
He left the television industry to study law and business, graduating from the University of Florida’s Holland Law Center (now Levin College of Law) and Graduate School of Business (now Warrington College of Business Administration) with both Juris Doctor and Master of Business Administration degrees, respectively, in 1982.
He is a former Fort Lauderdale, Florida city and South Florida state prosecutor, and practiced law for 21 years in his own firm. For more than ten years, he served as general counsel to the high-performing Housing Authority of the City of Fort Lauderdale, where he worked closely with its visionary former executive director, the late Dr. William H. Lindsay. He returned to journalism and newspaper publishing as his primary occupation upon the death of his father Charles, Sr. in 2004.
Cherry is a minority shareholder in and former general counsel of Tama Broadcasting, which owns nine radio stations. Since 1990, he has served in various capacities in radio stations in which he has ownership interests, from part-time deejay to general manager. In 1993, as a result of his experience as a prosecutor, he wrote the original EXCELLENCE WITHOUT EXCUSE: THE BLACK STUDENT’S GUIDE TO ACADEMIC EXCELLENCE, one of the best books ever written on improving academic performance for Black students. It is still used as a textbook in college-preparation classes and seminars. He reissued the original book with a new Introduction in 2013.
For the past 25 years, he has written commentaries, editorials, and stories for his other family-owned newspaper, the Daytona Times. His 30-minute radio commentary, Free Your Mind, has aired on WPUL-AM 1590, Daytona Beach, FL, since 2000. His award-winning weekly column, Straight, No Chaser, has appeared in the Florida Courier since 2006.
Cherry founded the Florida Black-Owned Media Coalition, Inc., a trade association representing Florida mass media owned by African-Americans, in 2006. He was elected to the board of directors of the National Newspaper Publishers Association, the trade association representing more than 200 African-American newspapers, in 2009. He also serves on the Government Affairs committee of the Florida Press Association, the trade association representing Florida’s newspaper industry.