Samuel, Jr. served in the French and Indian War (1754-1763). He never married. Until 1776, he and his brother Nathaniel shared a farm in Deerfield, Massachusetts. The farm was confiscated that year and sold in 1781, because Nathaniel was a violent, outspoken Tory. As a result, his enslaved man, Caesar Bailey, became Samuel's property. The Dickinson brothers shared Cato (also known as Dick Cato,) Caesar's wife Hagar, and possibly a girl.
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