Stede Bonnet lived a life of luxury in Barbados, inheriting from his father an over 400-acre sugarcane plantation, along with 94 slaves. But in late 1716, when he was 29 years old, Bonnet decided to leave behind his plantation, his wife, and his three surviving children, all under the age of 5, to become a pirate, despite having no experience even captaining a ship. As Captain Charles Johnson put it in A General History of the Pyrates: “He had the least Temptation of any Man to follow such a Course of Life, from the Condition of his Circumstances,” blaming it on a “Disorder in his Mind.”
So why did Bonnet leave behind his privileged life, and would he have made the choice again if he knew how it would turn out? Joining me in this episode to help us understand more about Stede Bonnet and his possible motivations is freelance historian Jeremy R. Moss, author of The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet.
Our theme song is Frogs Legs Rag, composed by James Scott and performed by Kevin MacLeod, licensed under Creative Commons. The mid-episode audio is “Oh, Better Far To Live And Die,” from The Pirates Of Penzance, written by Gilbert & Sullivan and performed by the D’Oyly Carte Opera Company and The Royal Philharmonic Orchestra in 1959, available via the Internet Archive. The episode image is: “Print engraving of Stede Bonnet in Charles Johnson's A General History of the Pyrates,” Public domain, via Wikimedia Commons. 
The HBO Show loosely based on the life of Stede Bonnet that we reference in the episode is Our Flag Means Death, created by David Jenkins and starring Rhys Darby as Stede Bonnet and Taika Wititi as Blackbeard.

Additional Sources:

“The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea,” by Amy Crawford, Smithsonian Magazine, July 31, 2007.

“The Life Of Stede Bonnet, The Gentleman Who Became A Pirate On A Whim,” by Genevieve Carlton, All That’s Interesting, August 9, 2022.

“A Pirate’s Life Was His, Stede Bonnet’s,” North Carolina Department of Natural and Cultural Resources, September 27, 2016.

“Top-Earning Pirates,” Forbes, September 19, 2008.

“Stede Bonnet and the Golden Age of Piracy: Part One,” by Danielle Herring, Library of Congress, December 8, 2022.

“Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the 'worst pirate of all time',” by Jeremy R. Moss, History Extra, March 3, 2022.


“A General History of the Pyrates: from their first rise and settlement in the island of Providence, to the present time,” by Captain Charles Johnson, 1724.


Learn more about your ad choices. Visit megaphone.fm/adchoices