Timothy, Jr. was a surveyor and soldier, having served in the Revolutionary War (1775-1783). He married Mary Wells, Jr., and it is said that they were "the richest couple ever married in Deerfield." (A History of Deerfield, George Sheldon, Vol. II, pg. 894) After losing their fortune, the couple moved to nearby Turners Falls, Massachusetts.
Timothy enslaved a man named Amos, whose tooth was extracted by Dr. Thomas Williams in 1749. The couple also enslaved a man named Caesar, whom Mary most likely brought with her when she wed Timothy.
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