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Ruby Pearl Diamond was from a Jewish family. Her grandparents Robert Williams and Helena Dzialynsky moved from Jasper to Tallahassee, Florida, with their five daughters at the conclusion of the Civil War. The family had some wealth and opened a store before purchasing three plantations for cotton production.

The Weekly Floridian dubbed Williams the "King of the Jews" in Tallahassee: all five of his daughters married Jewish men, and he gifted a Torah to the small Jewish community.

Williams's daughter Henrietta married Julius Diamond, a Tallahassee merchant and city commissioner in 1879. Diamond had emigrated from Prussia after the Civil War and was an early merchant in Tallahassee who owned several downtown buildings, an insurance business and farmland.

Henrietta and Julius Diamond had two children. Sydney Hamilton was born in 1883, and Ruby Pearl in 1886. Sydney was a well-known Tallahassee attorney.