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Houston Tillman "Red" Rainwater and his son, Jack Tillman Rainwater

When Roscoe Rainwater wrote in his 1972 genealogy, Here’s the Plan of The Rainwater Clan, that “...we have never heard of a Rainwater being a member of the chain gang..”, well, he hadn’t counted on H. T. “Red” Rainwater and his son, Jack.

Houston Tillman Rainwater was one of eleven children born to James Riley Rainwater, and his wife, Laura A. Rowell Rainwater. James Riley was a great-grandson of James Rainwater “the preacher.” The family lived in Carroll and Coweta Counties in Georgia. James Riley Rainwater was a cotton mill worker at a time in the un-unionized south when this occupation meant grinding poverty, and was often undertaken only after the family farm had failed. If one looks at Red’s long criminal career in this light, it’s likely he saw crime as an easy way out of the poverty of his childhood.

H. T., or Red, as he was known, left home early. He was living in Athens, GA in the 1920 census, and he moved to Dade County, Florida shortly thereafter. He married Elizabeth Lamar around 1921 and together they had three children: Jack T., Jean Elizabeth, and James. In the 1930 census, Red says he is a service station attendant, but he was, in reality, a bootlegger. When the bootlegging business dried up at Prohibition’s end, Red moved into the numbers racket, becoming a well-known bookie. He also leased Pier 5 from Dade County, a controversial move that was protested by local watermen. His 30-year career as the “Bolita Baron” of Dade County ended when a combination of tuberculosis, a recent gall bladder surgery, heroin addiction and a glass of milk ended his life in 1968.

Red’s son Jack Tillman Rainwater became a charter boat captain, which was probably a good cover for illegal activities. His most positive newspaper mention came in 1948 when he leased his charter boat, the Sea Gull, to the Miami Daily News, to take Mrs. William Richter out for a bit of deep sea fishing. Mrs. Richter landed a 50 pound 6½ foot sailfish and Jack landed some positive press. Most of the Miami New’s other coverage of Jack details his own career as a Bolita bookie. He died on 1 April 2007, his passing remarked by a nine word obituary in the Miami Herald.

Red’s other son, James, eschewed the family’s penchant for crime, and became a lawyer. He made the news in 1950, when he represented the “Brassiere Brigade,” female telephone company counting room employees who were accused of slipping rolls of quarters into their bras. Eventually the girls were freed for lack of legal evidence. In later years, he became a controversial law and order judge in Dade County. Privately, James and his wife Harriet were RV camping enthusiasts.

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