Robert Lee Calloway, Sr. was born on March 27, 1912 in Leesburg, Georgia (Lee County).   Oral history states that Anna Lamar and David Harris were Robert’s biological parents.  Reports are that David Harris died young due to illness.  Records show that Anna was about fifteen when she birthed Robert, and gave him up for adoption at the time of his birth.  Dan and Lucy Calloway of Leesburg, GA reportedly adopted Robert and raised him in their care.


When Robert was about eighteen years old, he married Sylvia Mae Jones.  Census records show that in 1935, Robert, Sylvia, and their two oldest sons were living in Palm Beach County, Florida.  Robert and Sylvia eventually produced five children from their union, Robert Jr., Willie Ellis, Bernard, Daniel, and Anita Faye.  All offspring lived well into their adulthood with the exception of Willie Ellis, who reportedly died of an aneurism at an early age.  Robert lived with his wife in Riviera Beach, FL for the duration of his life until his death on December 5, 1987.


Robert is remembered by many as being someone who could give you a swift “tongue-lashing.”  Though he only had a fourth grade education, he is also noted for being the first black caddie in Palm Beach County, demonstrating great skill in a sport where most blacks were excluded from during that time.




Sylvia Mae Jones, also known as "Sib", was born in Georgia on October 25, 1912 to Willie and Hannah Jones (c. 1887 and 1885 respectively).  She was one of four children to Willie and Hannah.  Sylvia's siblings were Sadie, Marie, and Sarah. 


In 1930, she married Robert Lee Calloway, Sr.  Their union produced 5 children.  Records show that Sylvia (also spelled “Silvia” on some records) lived in Palm Beach County for the majority of her life until her death on May 5, 1999 at the age of 86.  

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