Charles practiced law with the firm of Taft Stettinius and Hollister from 1955 to 1967 with three years hiatus while serving in the United States Army: eighteen months as an enlisted man and eighteen months as a Captain in the Judge Advocate General's Corps. He also served as Chairman and CEO of Taft Broadcasting Company and its successor Great American Broadcasting Company from 1967 until 1989. Charles returned to Taft Stettinius and Hollister for a brief time before being named Commissioner of the Ladies Professional Golf Association in October 1990 where he served until 1995.
He acted as personal business advisor to the late Arnold Palmer and Hall of Fame golfers Juli Inkster and Annika Sorenstam. Charles has served on numerous corporate and foundation boards and served as non-executive Chairman of U.S. Shoe, Cincinnati Bell and Convergys Corporation. He sat on the Presidential Board of Advisors on Private Sector Initiatives from 1985 to 1987. He was bestowed Honorary Doctor of Law degrees from both Miami University in 1980 and Ohio University in 1984. In 2000, he was named a Great Living Cincinnatian, the highest honor that can be awarded by the City of Cincinnati.