Born in 1804, Jack was the son of Rose and possibly the brother of a boy named Scipio, born in 1811. Rose and Jack were both enslaved by Charles Phelps of Stonington, a physician and town leader. In 1807 Phelps sold Jack, then about two-and-a-half or three years old, to Ebenezer Stanton and “leased” Rose to Stanton for a period of five years. Because Jack had been born after 1784, when Gradual Emancipation was passed in Connecticut, he would legally gain his freedom at age 21, whereas his mother, born in 1775 was ineligible for Gradual Emancipation and would have been considered a “slave for life.” Based on the terms of the sale/lease, Rose would have gone back to Phelps in 1812, while her son, theoretically, would have stayed in the Stanton household. However, Phelps died in 1808, and then Ebenezer Stanton, a sea captain, died in 1811. 

Records suggest that Rose may have moved to the household of Cyrus Williams, the son-in-law of Dr. Phelps, where a boy named Scipio, was born to a woman named Rose in 1811. The record does not show what became of her, though she may have been the older woman, also named Rose, who was named in a dispute between the towns of Ledyard and Stonington. Ledyard was helping to care for her in her advanced years, and because she was originally enslaved in Stonington, they were seeking compensation. As for Jack, a mariner named Jack Stanton who was 23 in 1827 (so born circa 1804) appears on a Seaman’s Protection Certificate, which prevented sailors from being “impressed” or taken into service by foreign mariners. He was born in Stonington, resided in New London, and was described as a “Colored Man” about five feet four inches tall. There are also several listings for “Jack Stanton” serving on ships out of New London in the 1830s and 40s. Whether this is the same Jack, we cannot know for certain.