Charles (Dan) D. Bailey Jr., a sixth-generation Floridian, was born in 1946 in Jacksonville, Florida, and raised in Sarasota, Florida. He received his BA degree in 1968 and JD degree in 1971 from Mercer University and was admitted to the Florida Bar in 1971.

Mr. Bailey is general counsel to the Sarasota-Manatee Airport Authority. He served for five years as the principal attorney for the Sarasota County Public Hospital Board. He also practices in the area of land use planning and zoning. He previously served as general counsel to the Clerk of the Circuit Court for Sarasota County. Mr. Bailey was selected by his peers for inclusion in The Best Lawyers in America 2007–2020; “Lawyer of the Year” in Land Use and Zoning Law in Sarasota in 2016; the 2006 and 2011 Florida Super Lawyer; and Florida Trend Magazine's 2019 Legal Elite.

His prior civic activities include service as president of the Sarasota Chapter of the American Red Cross; Sarasota County Civic League; Sarasota County Bar Association; Sarasota Tiger Bay Club; and service as Lt. Governor of Kiwanis, Division 21. He previously served as chairman of the United Way of Sarasota County and chaired the William G. & Marie Selby Foundation for nine years. He was the founding chair of Sarasota County Openly Plans for Excellence (SCOPE).

He is the father of four and grandfather of six.