Jack Woolsey was sold at the age of 19 to Henry Lloyd in Long Island; Jack joined Lloyd’s daughter’s (Rebecca) and son-in-law’s (Melancthon Taylor Woolsey) household. When her husband died, Rebecca retained legal rights to Jack. Rebecca moved to New Haven and into her daughter’s and son-in-law’s, James Hillhouse, home where Jack continued to be enslaved by Rebecca. Jack joined the crew of the Neptune as a cook. Neptune sailed from New Haven in November 1796 to the Falkland Islands and then to China, where the crew traded seal skins for silks, teas and other items. On the return voyage home, Jack succumbed to dysentery on July 14, 1799 on the voyage home in the China Sea.