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In late 1711 at the age of 17, Edward met Caroline Scott, a woman of modest but steady means. Their friendship began cautiously, as Caroline's hand had already been promised to the boorish son of a wealthy East India Company executive. But Edward's charms eventually won out, and he and Caroline were married within a year of their meeting; a union that angered her father, and got the whole of Bristol talking.
It happened during a darker period in his life that Edward revived an old idea of joining a privateering fleet sailing for the West Indies, with the aim of making war against the Spanish and collecting unchecked sums of gold and cargo. Discarding his wife's warnings, he left for the West Indies barely one month later, where he soon met with the privateer Benjamin Hornigold and his quartermaster, Ed Thatch.
Later, during his adventurous life, he survived a navel battle that left him close to death. Upon regaining consciousness, he met a man named Duncan Walpole, who was a Templar-turned-Assassins. Edward killed Duncan and took his Assassin robes along with a letter that he was to deliver to a man named Laureano de Torres y Ayala, a Master Templar. This event marked his fate and put him on a new and adventurous path toward becoming an Assassin.