Born in Bristol, Rhode Island, DeWolf was the ninth child of Mark Anthony DeWolf, descended from one of the settlers of the colony. He fought in the American Revolutionary War, and afterwards was a sea captain involved in the American slave trade. He retired from the sea around 1798, and became a successful farmer. He was elected to the Rhode Island General Assembly in 1808.[1] On May 8, 1818, the Rhode Island General Assembly replaced the existing judiciary with a contingent composed of five new members, all Democrats, including DeWolf.[5] After serving on the court, he returned to his private commercial ventures.[1]