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Despite the end of the War of the Spanish Succession, Hamilton gathered a fleet of privateers, including Henry Jennings and his eighty man ship, the Barsheba. Jennings and his group of dreaded and cruel sailors turned to piracy after the end of the war, and plundered the wrecks of the Spanish Treasure Fleet.
Hamilton was considered corrupt, appearing to have shared the plunder with Jennings and his pirates. At this time, he also issued a letter of marque to the slaver and privateer Laurens Prins, who expanded his slavery operations to Mexico.