The Gentleman Pirate with the Mid-Life Crisis: Stede Bonnet and the Golden Age of Piracy episode artwork

EPISODE · Jun 2, 2026 · 59 MIN

The Gentleman Pirate with the Mid-Life Crisis: Stede Bonnet and the Golden Age of Piracy

from History's Devils · host James Crossland

This week, James sets sail with Jamie Goodall (author of The Pirates of Chesapeake Bay and Pirates and Privateers) into one of the strangest true stories of the Golden Age of Piracy – the rise and fall of the so-called “Gentleman Pirate”, Stede Bonnet who abandoned wealth, status, and family for a life of crime at sea. Often described as a pirate driven by a midlife crisis, Bonnet’s journey from plantation owner in Barbados to notorious outlaw of the high seas is as chaotic as it is fascinating.Charting his brief but colourful career, we look at how Bonnet captained a ship despite his lack of sailing experience, his disastrous command decisions and his encounters with the notorious Captain Edward “Blackbeard” Teach. Along the way, we discuss where Bonnet fits in the wider tale of the legendary Nassau Republic, which dominated piracy in the Caribbean during the early 1700s.Check this one out if you enjoy pirate lore or have ever wished you could sail away with Blackbeard and wreak havoc on the high seas!Topics Covered in this episode:Stede Bonnet's origins in BarbadosThe War of Spanish Succession and the impact its ending had on piracyThe Nassau "Pirate Republic"Why hiring a pirate crew and paying them a regular wage was a bad ideaStede Bonnet's career in piracy along the eastern American seaboardThe way Stede Bonnet treated his crew and his style of captaincyThe story of Blackbeard, AKA Edward ThatchThe problems of Captain's Johnson's General History of the Pirates as a sourceHow Blackbeard took over Bonnet's ship, the Revenge and the rivalry that developed between the two menThe Act of Grace and how Blackbeard and Bonnet both sought a pardon for their crimes but then returned to PiracyThe Battle of the Cape Fear River that lead to Bonnet's captureHis escape from Charleston and re-captureStede Bonnet and Blackbeard's deathsThe ending of the Golden Age of PiracyChapters00:00 - The Gentleman Pirate Mystery01:14 - Why Steed Bonnet Became a Pirate03:44 - A Midlife Crisis at Sea06:23 - Was Bonnet Losing His Mind?09:22 - Early Success on the High Seas12:49 - Nassau: Pirate Republic15:03 - Meeting Blackbeard Changes Everything20:32 - Blackbeard Takes Control24:18 - The King's Pardon Arrives27:47 - Can a Pirate Go Straight?30:32 - One Last Voyage36:49 - Trial, Execution, and Infamy52:16 - The Legend of Steed BonnetFollow Jamie on Threads and Instagram @L_Historienne and on Bluesky @Lhistorienn and check out her website hereThanks to SOULFULJAMTRACKS for their tune "Dark Halloween"Follow HISTORY's DEVILS On Instagram @historysdevilshttps://www.instagram.com/historysdevils/On Substackhttps://jamescrossland.substack.com/Follow JAMES CROSSLANDOn Bluesky @jamescrossland.bsky.socialhttps://bsky.app/profile/jamescrossland.bsky.socialTag HISTORY's DEVILS@historysdevils#HistorysDevils #JamesCrossland #HistoryPodcast #History #DarkHistory #storytellingHistory's Devils is a podcast exploring the lives of murderers, charlatans, psychopaths, dictators, war criminals, tyrants, demagogues, revolutionaries, cult leaders, conquerors, fraudsters, and other controversial figures.History's Devils is hosted by James Crossland, professor of international history and author of:Rogue Agent: From Secret Plots to Psychological Warfare, the Untold Story of Robert Bruce LockhartThe Rise of Devils: Fear and the Origins of Modern Terrorism

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This week, James sets sail with Jamie Goodall (author of The Pirates of Chesapeake Bay and Pirates and Privateers) into one of the strangest true stories of the Golden Age of Piracy – the rise and fall of the so-called “Gentleman Pirate”, Stede Bonnet who abandoned wealth, status, and family for a life of crime at sea. Often described as a pirate driven by a midlife crisis, Bonnet’s journey from plantation owner in Barbados to notorious outlaw of the high seas is as chaotic as it is fascinati...

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