I recently read Under the Black Flag by David Cordingly (Amazon affiliate link) it was an interesting book.

It’s a book written in the 90s looking at the history of pirates during the golden age. It talked about some of the romantic myths that raised up around the golden age, and how those myths came to be.

The book shows how pirates lived and died, the difference between Privateers and Pirates. How the line between the two types could be blurred. And, what eventually lead to the down fall of the golden age of piracy.

The most interesting case, though one of the smallest in the book was Captain Kidd. Who was commissioned as a Privateer (complete with letter of Marque), crossed in to Piracy to appease his crew, and paid the price for it at the end. The political intrigue was a nice twist in the rope too.

What really lead to the end of the golden age of piracy was Hunt Teams (multiple ships hunting the pirates down), clemency (though some pirates went back to their former ways),  and visible reminders in ports of what happened to captured pirates. Countries not being at war led to some of the downfall too.

But the thing is, things had to change before piracy ended. The defenses put up around ports and along the gold trails didn’t do much to stop or deter the Privateers or Pirates going for the gold. For example, Henry Morgan’s attacks on Porto Bello, even though there were 3 castles protecting the place, it still fell to Morgan.

Ships carrying arms didn’t do much either, other than anger the pirates. It wasn’t until Naval vessels put on acts as either other Pirate Ships, or as merchant ships, that having armed sea going ships mattered.

The book did give some interesting history lessons, and gave some ideas that could be re-applied to cybersecurity to secure the Net Today. Think of the Internet as the Sea, and hackers as villainous pirates.

I also know I’m not the first person in InfoSec to read the book and draw some parallels between our industry and the Golden age of piracy. Adam Hogan talked about this a few times. I saw his talk at Bsides Columbus in 2017.

While a history book on pirates, it does give some ideas as to how to change how we’re doing InfoSec today. It was worth the time it took read, and gave some interesting thoughts on how to deal with the problems InfoSec faces today.

* Update 2024-10-01: changed to Amazon Affiliate Link, which I earn a commission from qualifying purchases.