Zephaniah Kingsley Jr. (1765–1843) made his fortune through slavery, over a long life that saw much of the Atlantic World during turbulent times. His father’s mercantile pursuits carried young Kingsley from Bristol, England, to Charleston, South Carolina, and then, because Zephaniah Kingsley Sr. was a loyalist émigré, to New Brunswick. When Kingsley struck out on his own in the early 1790s, he pursued the dangerous but lucrative coffee, sugar, and slave trades in the war-torn Caribbean, flying a series of neutral flags. In 1803, Kingsley moved to Spanish East Florida and transitioned into a planter. Now his nemeses were not privateers but the repeated filibustering expeditions launched from Georgia that sought control of East Florida and its annexation to the United States, typically settling for plunder.

Perhaps the biggest conflict that Kingsley had to navigate was the transfer of Florida from Spain...

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