After the war, Ben Tillman, his mother, and his wounded brother James (who died in 1866) worked to rebuild Chester plantation. They signed the plantation's freedmen as workers. They were confronted with the circumstance of several men refusing to work for them and legally leaving the plantation. From 1866 to 1868, Ben Tillman went with several workers from the plantation to Florida, where a new cotton cultivation belt had been established. The Tillmans purchased land there. Tillman was unsuccessful in Florida: after two marginal years, the 1868 crop was destroyed by caterpillars.