The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet

by Jeremy R. Moss

An heir to an established land-owning aristocratic family in Barbados, Major Stede Bonnet enjoyed luxuries equal to those of the finest houses in London. "A Gentleman of good Reputation" and a "Master of a plentiful Fortune," he was given "the Advantage of a liberal Education," but the call of the sea-and perhaps more significantly, the push of his obligations as a father and husband-cast Major Bonnet onto an unlikely and deliberate course toward piracy.
Easily likable, by friend and foe, many would be drawn to Bonnet. In his two short years of piracy, Stede Bonnet stood alongside some of the New World's most notorious pirates, including Charles Vane, Charles Condent (also known as "Billy One-Hand"), Robert Deal, "Calico" John Rackham, Israel Hands, Benjamin Hornigold, William Kidd, Mary Read, Anne Bonny, and the pirate to whom Bonnet would forever be connected, Edward Thatch (infamously known around the world as "Blackbeard"). Follow Major Bonnet through his improbable and exciting journey in the Golden Age of Piracy.

Genres: Nonfiction, History, Pirates, Biography, Historical, 18th Century, Biography Memoir

226 pages, Paperback

Published September 15, 2020

About the author

Jeremy R. Moss is a real estate developer, lawyer and lobbyist living in Jacksonville, Florida. An emerging author and freelance historian, Jeremy's research is focused on piracy and early colonial maritime history. When not working or writing, Jeremy is a family man and can be found telling stories of adventure and buried treasure to his young children.

Reviews

[Denise · Rating 4 out of 5]

I'll give you three guesses as to what led me to this book... (Yep, the OFMD obsession is still going strong.)
Moss's biography of the "Gentleman Pirate" is as well-researched as the sources allow and contains extensive sections from trial transcripts in its latter half. Certainly interesting reading for those intrigued by the prospect of learning more about the real history behind one of the most unlikely Golden Age pirates.

[Sanja · Rating 5 out of 5]

The first three episodes of S2 of Our Flag Means Death brought back my lifelong obsession with pirates and I wanted to learn more about the historical background of the Gentleman Pirate. The real version of him is much more depressing and definitely not as amusing and endearing, though I still can't really fathom why would freaking Blackbeard (the real one, not Taika's leather-clad sex-on-legs version 🥵) join Bonnet, not just raid his ship and be done with him but actually join him, unless he had some ulterior motive.

The real Stede Bonnet was quite frankly a madman. What kind of a pirate buys a ship instead of just comandeering one and pays their crew a salary? Who actually has that much money and still turns to piracy, just because they are bored? In the words of Izzy Hands, Stede f*cking Bonnet, that's who. And learning that he was as bizarre in real life as he is in the show was amazing, it was high time we got a show portraying his life, the jokes practically write themselves.

Anyway, quite an amazing book and I will definitely be reading more about the Golden Age of Piracy. In the meantime I will be continuing with S2 of OFMD and hoping for a different end for Stede and Ed.

(Did I turn this review into an ad for OFMD? I absolutely did. Go watch it. We need season 3.)

[Annabel_Hawkins · Rating 2 out of 5]

A solid, "zoomed in" look at a figure who typically vanishes in Blackbeard's shadow unless he's the butt of a historian's joke, this nonetheless offers little more than a gathering of quotes from popular pirate history books, and relies far too heavily on Johnson's /History/. To someone with very little knowledge of the figure, or someone just looking for an overview of his escapades before the Starz show comes out in the next year or so, this might be a great little volume. To someone who's read already read /Under the Black Flag/ and /The Pirate Republic/ (the two major popular histories on the Golden Age of Piracy, available at every single book store I've ever walked into) you've already gotten the overview, as the author cites them within the text.

I am keeping my copy of this however, as the reference charts of Bonnet's prizes are helpful/interesting, though I feel like I should fact check them before quoting.

[Belinda · Rating 3 out of 5]

A very dry, here-are-the-facts telling of the life of a very interesting man. Feels fairly substantial at about 200 pages about a man whose piracy career lasted all of 18 mostly unsuccessful months, until you realise that a couple of chapters are just "Blackbeard did things and Bonnet was also there" and could have been summed up in a few sentences. The last 100 pages are almost entirely direct transcript from Bonnet and his crew's trials which... isn't necessary, and is very hard to read. It also could have done with a map, I spent a lot of time googling locations.

That said, this is stunningly well researched and when it's good, it's very good. I'd absolutely recommend it to anyone who thinks they might be interested.

[Tera (adventuresbetweenpages) · Rating 1 out of 5]

DNF about the halfway mark. This book was ridiculous. If there isn't enough info on someone, don't write a book about them. Most of this book was information on cities and ports, other pirates. Most info was just quotes from other books. Makes me sad because I absolutely loved seasons one of Our Flag Means Death, which is loosely based off Major Stede Bonnet, so I was excited to find a book on him. But I'll be on the hunt for other books

[Daphne · Rating 4 out of 5]

Read this just because of internet historian and I am very pleased

[Joshua Gross · Rating 3 out of 5]

This was certainly well researched and cited multiple references. I found it interesting, especially as we had just been to Charleston and learned about Stede Bonnet. He was a gentleman in the 1700s who left his family to buy a pirate ship so he could be a pirate. He ends up joining with Blackbeard, being betrayed, getting a pardon, and then psychotically pirating his way up the eastern seaboard until he gets into a mess of a situation that leads to his arrest and capture. He then, dressed as a woman, tried to escape only to accidentally rat himself out and be captured again, eventually to be hung for piracy.

While the events described in the book were very exciting and interesting they were not written in a way that really helped draw the reader in. The chapters endings were abrupt, and the facts were the facts. But there is something to be said for learning the real facts of a story whether the book those facts are in is especially engaging or not.

[Scarlet Ingstad · Rating 5 out of 5]

This is a must-read for all pirate hisory fanatics!
It reads like a novel, but is all true, factual history based on the life and times of Stede Bonnet, a very underrated man. Bonnet came across and worked with some of the biggest names in the pirate world, including the infamous Blackbeard.
Highly recommend this book for anyone looking to understand more about the Golden Age of Piracy, some of its principle figures, and the world in which these men and women lived.

[Rosie · Rating 3 out of 5]

The first half of this was pretty interesting, but the second half was mainly made up of trial transcripts that were very dry. Would have been good to have paraphrased these and explained them a bit more, but still an interesting read for pirate enthusiasts and fans of Our Flag Means Death.

[Tara · Rating 1 out of 5]

Had I submitted this as a first-year essay in university, I would've failed.

[Joshua Martinez · Rating 5 out of 5]

Really a terrific read! For the history lover, fantastic historical context and dialogue during the trial. Highly recommended.

[Scott · Rating 5 out of 5]

Big reader of pirate history, here. I liked the format of Moss's book - half biography, half courtroom transcription, I think the last 60-odd pages (the actual court proceedings of Bonnet's trial) really set this book apart from books I've previously read.

Law isn't one of my interests, but it was cool to be transported 300+ years into the past for a word-for-word pirate trial (spoiler alert: as of this reading, Bonnet is 100% dead) - to see actual words said by a pirate, rather than the typical pirate history books that rely on what "likely would have" happened.

Good work, good sir.

[Mark · Rating 5 out of 5]

I really enjoyed the The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet. It is a story I knew nothing about and it was fascinating.

Stede Bonnet was living a very privileged life in Barbados. He had inherited a 400-acre plantation and had a wife and three children. He had been given the ceremonial title of Major. He was a wealthy, respected plantation owner that had a comfortable life. Then he effectively sneaks away from it all and purchases a ship, recruits a crew and declares himself a pirate leaving home and his family never to return or see them again. It is an amazing story to comprehend.

Obviously a traditional pirate does not purchase a ship, they steal a ship. Major Bonnet was not a traditional pirate. He also was likely not such a good pirate. His former background may not have prepared him well, as he fails in battle early on suffering defeat, injury and losing command of the very ship he paid for. He later has many adventures and misadventures, including meeting and teaming up with Blackbeard. Capture, trial, etc.

I’m not giving anything away as this is a historical account. And a fun, fast read.

[Jeremy Moss · Rating 5 out of 5]

Full disclosure, I'm the author!

What initially started out as a hobby grew into a passion and then into a reality. Since hearing Bonnet's story, how he left a comfortable family life for one of danger and adventure, I researched every piece of information I could find about Bonnet, including his trial transcript, in an effort to figure out "how" and "why" Bonnet would do that. Ultimately, that question, "why" may remain unanswered, but Bonnet's story is fascinating nonetheless - I hope to have done it justice.

Enjoy!

[Robin · Rating 2 out of 5]

"Every normal man must be tempted, at times, to spit on his hands, hoist the black flag, and begin slitting throats." (H. L. Mencken)

This biography tells the tale of one such normal man, an English plantation owner from Barbados who decides to buy a small ship, outfit it with cannons, and take to a life of piracy. The reasons for the change in vocation are absent from the historical record and unclear. The author suggests sympathies with the Jacobite rebellion or an unsatisfying home life; he leaves his wife and small children and never returns.

While it gets off to an intriguing start and the book seems effectively researched, throughout it I couldn't shake the feeling that Stede Bonnet was not a very apt selection for full length biographical treatment.

He didn't seem like a very successful pirate, for one. Because he lacked any experience with shipboard command he quickly gets critically injured in an ill-considered battle with a Spanish Man-of-war. Perhaps recognizing that Bonnet has no idea what he's doing, famed pirate Edward "Blackbeard" Thatch quickly usurps command of his ship, relegating Bonnet to a passenger on his own vessel. Bonnet remains in this situation for roughly half the book, lacking any apparent agency. He is quite literally "along for the ride."

After he parts ways with Thatch, Bonnet does manage to take some ships and engage in some plunder, but his exploits didn't seem particularly noteworthy compared to the other pirates mentioned in passing. He is a "Gentleman Pirate" because of his breeding, not due to any particular gallantry on the high seas. He doesn't seem to have been a particularly violent pirate, but then again most historical pirates weren't as bloodthirsty as literature and Hollywood would suggest.

Towards the end of his piratical career, Bonnet halfheartedly angles for a royal pardon but continues to board and steal from passing ships. Inevitably he gets captured and put on trial, and without spoiling things too much, he does not comport himself in a particularly manly or defiant way.

I have no complaint about the book's writing, just the choice in subject. Apart from the inciting mystery (i.e., what made this man drop everything to become a pirate?), he doesn't seem to have done enough to justify a whole book written about him. There doesn't seem to be enough historical documentation to make him anything more than a cipher. It seems like he was in over his head throughout his piratical career, but without diaries or other records of his thoughts and motivations it's difficult to come away from this book with any kind of moral or other instructive lesson.

This book is brief and competently written, but I wish I had spent my time reading about a more interesting and fully documented pirate.

[Cindy Vallar · Rating 5 out of 5]

We think of him as a failure. A man who lurks in the shadows of a stronger personality. A man who squanders his slim chance of evading the hangman’s noose by escaping. Yet none of this is why he engages those interested in pirate history. What intrigues them is the why. What compels a successful and well-respected gentleman to jettison family, friends, position, and wealth to pursue a life of crime?

He was a member of the elite of Barbados. He inherited a vast plantation. He married well and had four children. He even served as a justice of the peace. Like most people, he carried emotional baggage, some of which stretched back to his childhood, and it impacted this “ideal” life. So much so that one day, he purchased a sloop, fitted it out as a pirate ship, hired a crew, and went on the account. His name was Major Stede Bonnet. But he was a landsman, one who possessed little knowledge of sailing – a fact that would earn him no respect from those who served under him. A near-fatal misstep eventually led him to cross paths with a much-feared pirate who was a legend in his own time – Blackbeard.

Within the pages of this book, Moss shines a light on Bonnet from birth to death. Although he provides no definitive answer as to why this gentleman went on the account – Bonnet took that answer to the grave – Moss does share several hypotheses on this question. Along the way, he allows readers to see “the man behind the mask,” so to speak. For example, while we might deem Bonnet the least successful of pirates, his actual ill-gotten booty would equate to between five and six million dollars today.

The book is divided into two parts: The Life of Stede Bonnet and Bonnet’s Trial and Its Aftermath. Moss consulted many primary documents, some of which he quotes at great length within these pages. Where scant information is known, he fills in gaps with particulars from Captain Johnson’s A General History of the Pyrates. (Although a secondary source, much of the material on Bonnet can be confirmed from contemporary original sources.) In addition to the pertinent quotations that begin each chapter, Moss includes five appendices and actual transcripts of the trials. There is no index or a bibliography containing full citations of works consulted, although footnotes do identify sources.

The Life and Tryals of Major Stede Bonnet is an absorbing revelation of a pirate who often gets short shrift in histories of the golden age of piracy. It serves as an excellent review of this man and his life, as well a methodical examination of imprudent choices and the resultant consequences of them.

[Jennie Morris · Rating 4 out of 5]

I love a good pirate story, I mean, really who doesn't? Of course, the idea of being a pirate is way better than the reality living the life in the Golden Age of Piracy. Perhaps that's what Major Stede Bonnet thought, when he decided to forgo his comfortable life on a island plantation and turn to plundering and pilfering?

Jeremy Moss did a wonderful job with his novel "The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet". This biography reads like an adventure novel, instead of pages and pages of facts thrown at you like some books. Don't get me wrong, I love research and details, but how they're presented in the text makes a big difference in the reading. It's obvious Moss dedicated time reconstructing this gentleman pirate's life.

A young man with everything, Major Bonnet turned to piracy at 28. Married, with four children, and a wealthy plantation owner on Barbados, Bonnet seemed to have a well-made life. So why the sudden change? Why go from a steady life of comfort to swashbuckling outlaw?

Although the lived a life of comfort, Bonnet had his share of tragedies. It isn't hard to imagine the constraints placed upon his station. Without any actual maritime knowledge beyond pages of books, he buys a sloop, names it Revenge, and searches for a crew. Through trial and error, for two years he sets upon an adventurous and dangerous course of piracy.

Before reading this book, I'd never heard of Major Stede Bonnet. His tenure on the sea short, it's filled with incredible incidents of friendship, betrayal, mutiny, and revenge. Funny how we "remember" certain infamous pirates, like Edward Teach (Blackbeard) however Bonnet is often overlooked. His life reads like a fantastic make-believe tale, with such twisting plots, it seems almost unbelievable.

I recommend this novel to history lovers, pirate fans, adventurers, and anyone interested in 17-18th century Colonial and Caribbean history. Pick up this book, you won't be disappointed.

I received an Advance Copy of this book from Discovery.

[Dolly · Rating 3 out of 5]

Like many other reviewers, I was drawn to learning more about the "Gentleman Pirate" Stede Bonnet after watching the popular HBO series "Our Flag Means Death." This slim volume, just under 200 pages, is very accessible and straightforwardly catalogues Bonnet's comings and goings, starting with his origins as a landowner and family man to his deadly end as a convicted felon.

That being said, this is the work of an amateur historian and I think that shows. There is no formal bibliography at the end. Instead there are footnotes throughout with a lot of Ibids. That is not to say it is poorly researched; Stede Bonnet left no journals from his journeys. If I recall correctly, there are only two letters documented in the book that are written by Bonnet. Both are addressed to local authorities, begging for his release after his 2nd capture. Mentions of him in the historical record are rather sparse, which makes piecing together an accurate narrative of his life a challenge for anyone. However, the second half of the book is simply a reprinting of the transcript from Stede's trial without commentary or perspective from the author. I would have liked if Moss had given us some glimpse into his thoughts, even if it was a final chapter or separate section.

One of the book's strongest features is "Appendix V: A List of Those Prizes Taken by Major Stede Bonnet and The Revenge." It's a simple yet effective chart that lists in chronological order the booty Stede & Co. obtained from June 1717 to Oct 1718. I found it helpful to flip back to as I was reading. I used it to remember what had already been taken and what was to come - even if quite a bit of that looting resulted from the efficacy of Bonnet's crew or other pirates, notably Edward "Blackbeard" Thatch, rather than Bonnet himself.

Definitely worth a read if you want to learn more about this unique historical figure or, if like me, you wanted to see where maybe the TV show writers gleaned ideas and inspiration.

[Captain Marrow · Rating 5 out of 5]

Having an extensive collection of pirate history books, those like Moss's book on Bonnet are my favorite type of books; those that hyper-fixate on a particular pirate or location's history, or an element of history. There are countless books on Blackbeard, it's about time someone did Bonnet justice with his own devoted book. Of those that I have, I consider this, as a pirate historian from Charleston, the best book on Stede Bonnet.

For those reviewing who state the book can be dry at times, and there wasn't the excitement they had hoped for, sometimes that's just how history is. It's not always pleasant, not always action-packed, etc. I enjoy books like this, written academically, that are straight to the point with facts and don't beat around the bush. Having these tidbits of Bonnet's life all compiled together in a convenient, well-written package is something I lacked in my own personal library, and that slot on the shelf has been filled.

Keep it up Jeremy, wonderful job.

- Captain Marrow

[WTEK · Rating 2 out of 5]

I'm not going to lie, I picked this up after watching Our Flag Means Death. I wanted to see the real story behind Stede Bonnet. Well, you do and don't get that. You don't because there just isn't enough documentation to see what this man's motivations were or what his interactions with other pirates were like. There was, however, a number of facts about his whereabouts and plundering.

Unfortunately I just couldn't finish this book. I wanted to like it. There were interesting facts in it. But overall it was written a bit like a high school report on Stede Bonnet. There was an abundance of direct quotes from the author's resources that he then went on to basically paraphrase. It would have been more engaging and would have drawn me in more if he would have footnoted without using the direct quotes to create a story that flowed better. You can stick to the facts and still use a story narrative style to make history more engaging.

[Celestarius · Rating 3 out of 5]

I originally bought this after watching the first season of Our Flag Means Death, as I was curious what parts were taken from actual history (obviously not expecting the show to be super accurate). I only just got around to reading it after watching (and disliking) the second season of the show, but anyway, I found it fairly interesting.

While it focuses on Stede Bonnet, as the title implies, Moss also includes details about other pirates of the time and aspects of pirate life, all pulling from historical record. It's definitely a history book and not a narrative retelling of events. While that does make it a bit dry at times, it's also neat to read original source material (much with alternate spellings and misspellings intact) from some of the figures involved in the events covered. This includes a somewhat lengthy section of court documents from Bonnet's trial (which, full disclosure, I skimmed a bit because it was so long).

[Jen Well-Steered · Rating 4 out of 5]

Try to read this without picturing Stede and Ed making out on the beach outside the Royal Privateering Academy, then agreeing to meet at dawn and run away to China.

That probably didn't really happen, but it's surprising how much of the show is more or less based in fact, from Stede abandoning his wife but taking his books with him to the entire crew being abandoned by Ed on a desert island. The book also deals more with the things the show sort of glosses over, like the fact that Stede's money came from owning a sugar plantation in Barbados that was worked by slaves.

Highly recommend for fans of Our Flag Means Death who want to know more of the real story.

[Andrea · Rating 2 out of 5]

I really wanted to like this book, I really did. But it lost me at chapter 20, which was one long citation, which continued until the end of the book. I can see the usefullness of viewing the trial as it actually was, but especially the transcript for the trial of the crew did not give me as a reader anything. Feels like a collection of citations more than anything else.

[Dollhaus · Rating 3 out of 5]

I like nonfiction books, I do.

What I don't like are dry non-fiction books. This felt a little too academicy and reporty for a good read.

Don't get me wrong, this book is very well researched and is full of interesting facts. It just... isn't fun to read. I want a bit more of a narrative structure. This just lists the information and says who did what and where.

[Angela · Rating 4 out of 5]

Really enjoyed learning the details of Stede's short and pitiful life. Running off and becoming a pirate is very tempting, my guy. I know. Loved the rueful letters he wrote trying to get out of his death sentence. Loved his attempt at escape disguised as a woman. Next time im walking around on a ship in my dressing gown reading a book i will pour one out for my homie.

[Scarlett Bryant · Rating 2 out of 5]

Bought this book because it is the real life person who Stephen Bonnet’s life is based on from Outlander. Enjoyed the first 40 pages about his life but most of the book was about specific pirate battles which wasn’t really my vibe. Would reccomend if you think nonfiction prate battles are interesting, otherwise I would probably skip it.

[Helena · Rating 4 out of 5]

Very interesting book, especially the first two thirds. There was too much focus on trial recordings towards the end though, which could have been better summarised by a few blocks of text, so I skimmed a lot of those. Really good to read the history that Our Flag Means Death was loosely based on!

[Laura · Rating 3 out of 5]

Meh. Giving an extra star because I love Stede Bonnet in his Our Flag Means Death version but it seems I prefer to take my history with a dollop of fiction. Controversial!

(It was good fun to find out which bits of the show were based on historical accounts of actual events.)

[paige janusek (^з^)-☆ · Rating 2 out of 5]

i’m not the biggest fan of nonfiction but it was pretty interesting ngl

[Sadie Basem · Rating 4 out of 5]

I read this after watching OFMD and it was really neat to compare the history with the show. The author was very thorough in his research!