Mr. Weatherspoon, a native of Cairo, Georgia, attended Boys High School; and St. John University, Empire State College, and Hunter College in New York. He achieved a Master's Degree in Business Administration from Strayer University in his later years. After serving, with honor in the United States Air Force, he also served on various boards and councils for the advancement of communities throughout the New York metro area, from the South to New England, on to East Africa. He was an advisor on education outreach programs, a project strategist, most notably in the area of telecommunications in East Africa.

Mr. Weatherspoon was revered as an entrepreneur, a real estate developer, and investor. He held 14 director, organizational president, medical administrator, and educational positions throughout his life. The positions he held were numerous but he dedicated special time and attention to the Upper Dorchester County Ministerial Alliance and the Dorchester County Democratic Party over the past several years. Though he worked hard, his favorite pastime sport was baseball, as he emulated his cousin and favorite player, Jackie Robinson.

In his private life, Mr. Weatherspoon assumed the role of patriarch, family-history griot, and respected, learned counselor. Kenneth Weatherspoon Sr. was preceded in death by his wife, Mary Britt-Weatherspoon, one son, Ronald Weatherspoon, his parents Arch Weatherspoon and Grace Weatherspoon, siblings, Joseph C. Weatherspoon, Roosevelt B. Weatherspoon, Janie Lee (Weatherspoon) Green, James W. Weatherspoon, Archibald Weatherspoon Jr., Grace J. (Weatherspoon) Fraser, David Weatherspoon. He is survived by one brother, Mr. Vernon L. Weatherspoon Sr. of Richmond, VA.

Mr. Weatherspoon leaves many loving and cherished memories to children, Kenneth R. Weatherspoon, Jr. and life-partner, Ovella Wilson; Ronald's children, Ronald Jr., Djaris, Nicole, Phadon, and Mary Grace; Patrice (Weatherspoon) Walker; two sons, Donald and DeWayne and Aletha (Weatherspoon) Lockett, son-in-law, Jerry B. Lockett, two sons, Rashawn and Demetrius Featherston; Gary Weatherspoon, daughter-in-law Cherita (Griffin) Weatherspoon and their four children, Emile, Corban, Jaden, and Ian;  He also leaves a host of great grandchildren, nieces, nephews, brothers and sisters- in-law, and cousins to carry the torch.