On June 4, 1946, Simon Randolph, Jr. was born in Suwannee County, Florida to the late Simon and Sarah Graham Randolph, Sr. Later the family moved to Monticello, Florida where he graduated from Howard Academy in 1967. He was converted and baptized in 1978 and joined St. Rilla Missionary Baptist Church in Lloyd, Florida, which was the family's church. While attending St. Rilla, he joined the choir and later the St. Rilla male chorus. Simon was known for displaying a big smile whenever his favorite song  "I won't complain" was heard.

Simon was employed by Artistic Creations (The Apron Factory) for several years. Being multitalented, he also started his own business on the side, Simon's Woodworks. Simon was known for crafting all sorts of wooden objects such as signs, name plates and various figurines.

On September 4, 2020 at 12:31am, God called his name. "Simon, good and faithful servant come home," our Master said.

He leaves to morn his passing, his loving wife, Mary Louise Gaffney Randolph of Monticello, FL; his brother, Simon Randolph, Jr. of Tallahassee, FL; his sister, Willie Mae Campbell of Canton, OH; his stepchildren, Jacky Gaffney and Willie Ann Smith of Monticello, FL, his grandchildren, Raymond Smith of Miami, FL and Tamar Smith of Albany, GA; his nephew, James (Laleatha) Macon of Woodville, FL and Calvin (Shakeira) Salters of Monticello, FL; his niece, Miesha (Antonio) Dawkins of Crawfordville, FL; four sisters-in-law; six brothers-in-law; and a host of other relatives and friends. Simon was preceded in death by his sister, Minister Rosena Randolph Macon Singleton.