Soon they began using the lifeboat to fool passing ships by posing as shipwreaked sailors. They would paddle out near a vessel, and once they were close enough brought out their guns and demanded supplies. The pair continued this trick for several years and were very successful, until one day Caesar and the sailor had a quarrel over a young woman taken from a looted ship. Fighting over her, Caesar killed his friend in a duel and took the woman for his own. Caesar had recruited men from the looted ships to join him in piracy. After a while, they grew in enough numbers to attack ships on the open sea. He and his crew were often able to avoid capture by retreating into Caesar's Creek and other shallow inlets between Elliot and Old Rhodes Key and onto the mangrove islands.
It was said that he and his men buried 26 bars of silver on the island, although no treasure has ever been recovered. Apparently he had a harem on his island, reportedly having at least 100 women seized from passing ships, as well as a prison camp which he kept prisoners in stone huts hoping to ransom them. When leaving the island to go on raids, he left no provisions for these prisoners and many eventually starved to death. A few children reportedly escaped captivity, subsisting on berries and shellfish, and formed their own language and customs. This society of lost children gave rise to native superstition that the island is haunted.
Caesar eventually left Biscayne Bay to join the infamous pirate Blackbeard. A man of keen intelligence, he served as a lieutenant on Blackbeard's flagship Queen Anne's Revenge. In 1718, after Blackbeard's death battling with Lieutenant Robert Maynard at Ocracoke Island, Caesar attempted to set off the powder magazine of the ship as Blackbeard had instructed. However, he was tackled as he prepared to light a trail of gunpowder leading to the magazine, and was restrained by several of Maynard's sailors. Taken prisoner by Maynard, he was later convicted of piracy and hanged in Williamsburg, Virginia.
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