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Jenkins was a member of the Royal Navy who infiltrated the crew of the pirate captain Edward Thatch, serving until 1718, when he met with his British commanders at Ocracoke. There, an ambush had been set for any pirates who arrived, including Thatch, who had called the gathering to celebrate his retirement.
In conversation with his commander, Robert Maynard, he elaborated on Thatch's apparent insanity, explaining that the pirate drank ale with gunpowder mixed in, and occasionally locked his crew in the hold and lit sulfur and other chemicals to test their resolve.
During his rendezvous, Jenkins' sly movements attracted the attention of Edward Kenway, who pursued him through the outlying jungle and witnessed him signaling the Royal Navy to launch a mortar attack on the encampment. In the ensuing battle, all of the pirates present, save Kenway and his crew, were killed.