By 1656, Leader was in Barbados, where he engaged in sugar-refining and salt manufacturing. In a letter from 1660, he complained about the island's climate and stated that if it wasn't for the slave labor available in Barbados, he would prefer to reside in New England. He also wrote that he intended to leave "this western world" for Ireland, as he saw "no place either for profit or pleasure so good as Ireland", which was remarkable considering that conditions there following the Cromwellian war were very poor. Illness prevented Leader from leaving Barbados until the spring of 1661. He died in Kittery on December 27, 1661. He was survived by two daughters, Elizabeth Hole, who was killed by Native Americans on May 4, 1705, and Anna Clark of Portsmouth, New Hampshire, who lived until at least 1723.