 In 1689, Coates originally signed aboard the "Jacob" as a sailor in a privateer expedition, then under the command of Captain William Mason, and commissioned by the colonial officials in New York to raid French shipping off the coast of Quebec ""to war as in his wisdom should seem fit"".However, unable to find French vessels, Mason began raiding English shipping and distributing the spoils among his crew, including Coates, eventually adding up to 1,800 pieces-of-eight per crewman.Possibly withholding a portion of the crew's shares, Mason disappeared after stopping at an island in the Indian Ocean; he had actually returned to New York with some of his crew and his quartermaster Samuel Burgess to divide the spoils, later returning to the area as captain of the "Pearl".