Samuel Dickinson, 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. Nathaniel was an active, outspoken Tory and fled Deerfield in 1775. His activities led to the confiscation of his property by the Deerfield Committee of Safety and Correspondence in 1776 and his banishment from Massachusetts in 1778. As the co-owner. Samuel was allowed to rent Nathaniel's share of the farm for one year, but Nathaniel's confiscated property was auctioned in 1781; the proceeds of the sale were paid to the state treasury.
In his claim to the British government for compensation for property confiscated as a result of his loyalty to the Crown, Dickinson included "A Negroe Man, taken by the rebel committee, and held in the army worth £50 strg." This was likely Caesar Bailey of Deerfield. The Dickinson brothers also shared Cato (also known as Dick Cato,) and Caesar's wife Hagar. Caesar Bailey served in the Continental Army during the American Revolution (1775-1783); it is not clear if or when Bailey and his wife were emancipated before slavery ended in Massachusetts.
Samuel Dickinson died in Deerfield in 1780, predeceasing his exiled brother by five years.
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