Henry Jennings was a notorious pirate who operated in the Caribbean during the late 17th and early 18th centuries. Born in England, Jennings began his career as a sailor and privateer. He was known for his cunning and successful raids, including the capture of the Spanish treasure galleon “Nuestra Señora de la Encarnación”. After retiring from piracy, Jennings lived a quiet life in the Bahamas and died in the early 18th century. His legacy as a successful pirate leader lives on in pirate folklore and popular culture.

Henry Jennings Historical Background

Jennings was one of the most notorious pirates to ever grace the Caribbean seas. He was born in 1683 in England where he first began his love for sailing at a young age. By age of 18, he joined a crew of privateers and sailed to the Caribbean. Here, he quickly gained notoriety as a ruthless pirate by attacking Spanish vessels and trading between ports with contraband goods. In 1713, he captured three Spanish merchant vessels near Havana, earning him recognition among pirate circles for his bravery and tenacity.

Jennings was highly active throughout the Caribbean basin both as a legitimate trader and privateer. He was instrumental in harassing Spanish shipping and trading activity in the waters near Hispaniola and Jamaica during Queen Anne’s War. His successful raids earned him money and fame but also heightened tensions with Spain and other European powers seeking to protect their trading interests in the region.

As one of the most renowned pirates active in the Caribbean, Jennings had close relationships with several other famous and successful buccaneers. Jennings formed a bond with the malicious pirate Charles Vane. Jenning harnessed Vane’s wickedness for his own advantage but eventually parted ways over a difference of opinion regarding the King’s Pardon.

While the legacy of Henry Jennings is mostly forgotten in the annals of history, the impact he made on the world during his lifetime is undeniable. During his heyday as a captain, Jennings’s capture of the Spanish Treasure fleet wreckage played a significant role in the growth of piracy. To this day, some of Jennings’ booty – including signed papers from British colonial governors and other precious items – can still be found in various museums and private collections around the world.

Life Events & Timeline of Henry Jennings

• Born in 1683 in England
• At age 18, joined a crew of privateers sailing to the Caribbean
• 1713 Captured 3 Spanish merchant ships near Havanna
• 1715, July 31st, the famous ‘1715 Spanish Plate Fleet’ was destroyed by a hurricane off the coast of La Florida near present-day Vero Beach.
• 1715, November 24, sloops Eagle and Bersheba under Captains John Welles and Henry Jennings receive commissions from Jamaica Governor Archibald Hamilton for privateering.
• 1715, December 27, five pirate ships led by Henry Jennings and Charles Vane attacked Spanish salvage teams attempting to recover the wreckage of the Spanish silver fleet. They managed to plunder £87,000 in gold and silver with some reports saying it was up to 350,000 pieces of eight.
• 1716, April 3rd, privateer Captain Henry Jennings meets fellow pirates Samuel Bellamy and Paulsgrave Williams. The next day they capture the French merchantman St Marie. Jennings leaves to capture the ship Marianne and while gone is betrayed by Bellamy and Williams who escape with 28,500 pieces of eight.
• 1716, May 19th, Governor of Jamaica, Lord Archibald Hamilton is arrested for enabling Henry Jennings, Francis Fernando, and Leigh Ashworth to commit acts of piracy violating Spanish treaties.
• 1716, Oct, Gov. Archibald Hamilton is sent from Jamaica to England, for trial.
• 1715, Nov, the fleet with Hamilton is separated by the wind. Jennings captures the governor’s ship, Hamilton Galley, holing them hostage 4 days before leaving with 20 tons of rum. The negotiations and scheming among all onboard were no doubt interesting, but lost to time.
• 1717, December, Jennings accepts the King’s Pardon and publicly retires from piracy.
• 1718, allegedly he, like Benjamin Hornigold, took a commission to seek out and capture his former crewmate Charles Vane. Likely for the reward and to secure his own pardon. Or perhaps to warn Vane and help him escape.
• 1745, during the War of the Austrian Succession, he was captured by the Spanish and presumably died in custody.

Henry Jennings Artwork

There is a distinct lack of paintings, drawings, or even completely fictitious art of Henry Jennings that has survived till today. Trying to track down some good concept art for the character proved difficult. Most of what I found was purely conjecture or random “cool modern pirates”. None of it really appealed to me, but here are a couple of highlights if you’re interested:

Henry Jennings in The Lost Pirate Kingdom Documentary Series

“The Lost Pirate Kingdom” is a six-part historical documentary series available on Netflix. The series explores the real-life stories of famous pirates such as Charles Vane, Samuel Bellamy, and Blackbeard, and provides a glimpse into the golden age of piracy in the 18th century. The series is a combination of reenactments, interviews with experts, and CGI footage that examines the rise of piracy and the formation of their own democratic society in Nassau. It also explores the conflicts between the pirates and the colonial powers, as well as the impact that piracy had on global trade and commerce.

The show delves into the harsh realities of pirate life, the brutality of their raids, and the political tensions that ultimately led to their downfall. Through interviews with historians and dramatic reenactments, “The Lost Pirate Kingdom” offers a compelling look at the world of piracy and its lasting impact on the region and its role as a prelude to the American Revolution. If you’ve not yet watched it, I highly recommend you add it to your Netflix queue!

Henry Jennings Miniature

As a wealthy landowner and gentleman of wealth, I like the Lost Kingdom’s interpretation of Jennings. The film portrays him a little older than he was at the peak of his career (sorry ) as he was 30 at the time of the Silver Fleet raid. But you can just blame it on the wig making him look older than he really is.

He was no doubt a shrewd man capable of commanding fear and respect from others. Henry was able to negotiate a commission as a privateer from Governor Archibald Hamilton in a non-wartime state. He was also clearly a man of authority and power as he was able to bring Charles Vane under his command and use him as an enforcer of sorts.

How To Kitbash a Custom Henry Jennings Miniature

Parts List

• Body – Militia B4
• Left Arm – Militia E1
• Right Arm – Militia E5 for the arm. I cut the musket hand off and attached a Sailor P42 hand with a sword
• Scabbard on hip – Sailor P32, but I cut the hilt portion off so the scabbard appears empty
• Pistol – random Sailor Pistol P33 or P34
• Head – Box of Plunder, head with the separate ponytail and bow at the back.
• Wig curls – see below
• Book – see below

Body & Arms

For the body, I started with a base Soldier model as the overcoats are of a classier nature than the standard sailor. However, it was a bit too “button-y” for my liking. I instead went with the Militia B4 body. It still has a snazzy jacket and a neckerchief that favors the Lost Kingdom portrayal. Perhaps it came loose and got a bit ruffled during the fighting.

The militia box is disappointing in that 100% of the models have muskets in two hands. I took that as a challenge in creating conversion minis that converted them to single-handed weapons. For this model, you are moving one set of Militia arms to a different body. Unfortunately, this is a bit of a pain. The body B4 has half of the left arm from the shoulder to the elbow attached to the body. You’ll have to cut the body at the shoulder to attach the new arms. Make sure the measure and fit the new arms MULTIPLE times while you are cutting so you get a good fit.

Head

The head is the fiddliest bit to get right. I had to trim it multiple times and trim the collar and edges of the jacket to get it to fit in the slot properly. Dry fit it in place multiple times and keep your fingers safe. As I shared before, I use a self-healing cutting mat that helps absorb the model a bit so it hopefully doesn’t roll/flip across the room as much (… in theory). If you don’t have one, I highly recommend picking one up.

Creating a Custom Wig

What refined gentleman would not have a powdered wig fitting for true period fashion?  To create this style I had to get a bit creative.  I started with the base head with the ponytail and bow from the Box of Plunder.  To enhance it and add side curls, I cut two small lengths from an extra Calvary arm with a Lance.  You could also use one of the boarding pikes.  Or if you didn’t want to sacrifice a plastic mini bit, you could improvise with a thick bread bag tie or a paperclip. 

Creating A Ship’s Logbook

In the mini-series, there is a scene where Jennings is interrogating another captured captain about his logbook (screen clips above).  I loved the concept of Jennings intimidating the captain into revealing his hidden stash and items not in the main cargo hold.  With his lap dog Charles Vane at his side, it was likely quite an efficient tactic!

To craft the book I cut the outer cover from a Domino’s gift card.  I initially cut a long rectangle and then folded it in half to create a crease. I also cut another thin strip the same width to function as the spine of the book. The pages are simply cut from a scrap piece of paper slightly smaller than the cover. I cut about 12-14  sheets and stacked them neatly, coating them with white PVA glue in between.  Add as many pages as looks good.  

Once the book was dry I primed and painted the cover and put a wash of skeleton bone contrast paint on the pages.  Doodled some words with an ultra-fine point Sharpie marker.   Then for a final touch, I added a thin red bookmark using a piece of cross-stitch thread from my wife’s sewing supplies. I cut it to length and then rolled it between my fingers that were coated with PVA glue.  This gives it some stiffness and keeps it from fraying into individual threads.  Later when I was finishing painting the red on the scabbard, I thoroughly wet my brush and dripped some blood splatters on the pages for effect.

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Painting the Henry Jennings Miniature

I, unfortunately, don’t always keep close track of the paints I use while I’m working. I just sort of wing it grabbing paints on a whim based on what looks good. The base jacket was a flat “black “pavement” craft paint and then a coat of “Ultramarine Blue” Citadel Contrast Paint. Some misc greys/blues for highlights.

The skin is Contrast Gulliman Flesh, if you only buy one contrast paint, this is the one to get. On most models, it’s a single coat and done and you have great tabletop-quality skin (90% of my sailors and European models are this way). I added a layer or two to lighten the model cause I imagine Jennings being a bit of a pasty aristocrat.

The decking is a couple of coats of Skeleton Horde contrast paint. I vary between a single thick coat and two thin coats, but I like the variance the paint gives straight out of the container.

Henry Jennings Flag

Flags played a crucial role in the history of piracy, as they served as a symbol of identity and intimidation. In the early days, they were often simple red or black squares to indicate no quarter would be given. Later pirate flags were designed with distinctive imagery, such as skulls and crossbones or red flags, to strike fear into their victims and announce their presence. Pirates would hoist their flags before attacking a ship to give their victims the chance to surrender without a fight.

The most famous pirate flag is the “Jolly Roger,” which had a skull and crossbones on a black background. It’s become the symbol of piracy for centuries. Many pirate crews would create custom flags as personal symbols to help bolster their reputation. Depending on the flag flown, merchants and enemies knew the level of risk they faced based on the tales of the brutality of the crew pursuing them. The use of flags by pirates became so significant that many countries passed laws outlawing their use.

The accuracy of the details of the flags of many crews is questionable as there are a number of myths that have arisen over the years. There have been several fictional writers and artists that have twisted up reality and so many flags attributed to captains should be taken with a grain of salt. That said, custom flags for commanders and crews a FUN way to add some creativity to your games.

Artistic Version of Henry Jennings’ Pirate Flag

Henry Jennings allegedly flew a black flag with a skull and crossbones over an hourglass. The hourglass was meant to warn enemies that their time was running out and to urge them to surrender quickly before it was too late. Below is an artist’s rendering of a possible flag flown by Jennings.

Henry Jennings as a Commander in Blood & Plunder

As a veteran commander, he comes with 3 Command Points and a 12″ command range putting him at the top of the list for capability. He began his career as a privateer so he has the option to command British Privateers. After giving in to his base nature he turned to full-blown piracy. Joining in a loose alliance with the other greats of Nassau he also can command both the Golden Age Pirates or The Flying Gang.

Special Rules Breakdown

He has 3 special rules:

• Bold – It’s typically better to avoid being Shaken or entangled in Melee, but this lets him continue to bark orders and use Command Points without limitation.
• Very Inspiring – This is fitting for a venerated leader like Jennings. Being able to reroll any failed Fatigue Check on any unit in command range will help you keep the Fatigue at bay and your units shooting at maximum speed.
• God’s Blessing or the Devil’s Luck – Granting an extra Fortune Point lets you do all sorts of fun things. Check out our Fortune Points Strategies and Tactics article for more ideas.

Force Lists With Henry Jennings

Henry Jennings is an expensive commander, which is fitting his years of experience and skill.  But at 30 points I personally wouldn’t recommend him in lists under 200 points. He also lacks Commodore so he’s not the top option in larger 400pt+ games that may feature multiple ships. I think his sweet spot is 200 and 300 point forces.

200pt British Privateers by Jayden King

This Force focuses on attacking enemies at mid to close range with the eventual goal of boarding and capturing the vessel. I recommend that you put the large unit of Sea Dogs on the 4 Swivels on the Fore Deck along with the larger unit of Jamaican Privateers. Assign the Able Seamen to the 2 rear swivels along with the other unit of Jamaican Privateers on the same deck. The Officer helps keep the Inexperienced units firing. He costs 8 points which is the same cost as “Trained” on one of the two units, but as the benefit of serving as a backup commander if Jennings is killed.

https://forcebuilder.bloodandplunder.com/shareforce/a6338eb7

200 pt Flying Gang Pirates by Garrett Swader

This is a Pirate version of Jennings leading the group of Flying Gang pirates. This force has 4 Swivels on the Fore Deck to soften its target as it approaches to board. The Jamaican Privateers and Euro Sailors are both use Muskets to add additional fire at long range. Once engaged in boarding the Sea Dogs and Pirates provide close combat skills and the Ruthless faction ability will hopefully help you inflict more hits.

Force Setup & Strategy

• Put the pirates with Jennings and the Jamaican Privateers with the Loyal Quartermaster up front.
• The Seadogs on swivels and Euro Sailors with muskets in the back.
• Your goal is to close on the enemy as quickly as possible using the rear deck of swivels and brace of pistols to soften your target and inflict fatigue. The two front deck units should stay prone until they are ready to throw grapples. Then stand up, Grapple, and start the boarding fun. Don’t forget to throw your explosives!

https://forcebuilder.bloodandplunder.com/index.php?builder&forceid=44407e20

300 pt Golden Age Pirates by Jason Klotz

Historically, Jennings was the owner of a 40-ton sloop of war with 4 guns known as the Barsheba (Bathsheba). That size ship is viable as a Bermuda Sloop, Balandra, standard Sloop, or even a Brigantine. This list uses a larger “Sloop of War” variant of the Brigantine armed with 4 Medium Cannons.

Force Setup & Strategy

• Fore Deck: 4 swivels with 12 sea dogs armed with melee weapons only and 5 roundsmen to max the capacity of the front deck. You may want to start the Roundsman prone for at least one round as you approach to minimize casualties and fatigue on the small unit.
• Mid Deck: 4 Medium Cannons with Grapeshot manned by the Zeelieden and a Master Gunner to keep firing quickly. There is a small squad of 6 Roundsman in the middle with long-range weapons that pair with the cannons.
• Rear Deck: 2 units of Late Flibuistiers, the larger unit w/Jennings.
• The force also has a sharp-eyed lookout to help win the role as the attacker so you can take advantage of the Golden Age Pirates’ False Colors ability.
• During initial deployment, unless they are a cannon heavy force, I would try to sail parallel to my opponent or even slightly away from them. I would stay in the 16 to <24″ range and shell them at long range to try to inflict a bit of Fatigue and some casualties. There are plenty of command points and veteran units to keep firing every round with muskets and a high rate of fire with the Grapeshot.
• The Golden Age Pirate free Grapeshot lets you choose between roundshot or grapeshot. The advantage of grapeshot is you start with a base 4 instead of a 6 like Swivels. That means if your opponent is running a Swivel boat, and you try to stay at 20″ you are hitting on 8s vs 10s on Swivels. Alternatively, if they have a small ship you can opt for Roundshot and do some damage to the hull.

https://forcebuilder.bloodandplunder.com/shareforce/8de81ec3

Final Thoughts on Henry Jennings

Suggested Additional Reading

• Create a custom Benjamin Hornigold commander model
• Check out the legendary Edward “Blackbeard” Teach, Stede Bonnet, Charles Vane, and Amaro Pargo miniature showcase articles.
• Check out the Golden Age Pirate Faction here.
• Check out our other painting related articles here on Blood & Pigment.
• Check out this guide to assembling the new multi-part plastic models from Raise the Black.

Related Products

• Kitbashed mini requirements
  • Sailors or the Blood & Plunder Blackbeard vs. Maynard 2 Player Starter Box (Contains Blackbeard, 2 ships, and 24 crew models)
  • The Soldier Boxed Set – Model body
  • The Cavalry Boxed Set – Optional for the arm
• 6th Rate Frigate (Mary)
• Blood & Plunder: Raise the Black Expansion (contains the rules for Jennings and his factions)

The article, kitbashed mini, and miniature painted by Jason Klotz (except where noted)

References

• “Pirate Biographies: Henry Jennings of Bermuda and Jamaica“
• Colin Woodard: The Republic of Pirates: Being the True and Surprising Story of the Caribbean Pirates and the Man Who Brought Them Down. Houghton Mifflin Harcourt, 2008, ISBN 9780547415758, pp. 103-112
• Historica: Henry Jennings Biography https://historica.fandom.com/wiki/Henry_Jennings
• “Captain Balchen, H.M.S. Diamond, to Mr. Burchet, May 13, 1716”; “List of [10] Vessels Commissioned by Governor Lord A. Hamilton.”
• “Deposition of Joseph Lorrain, August 21, 1716, Jamaica,” Jamaica Council Minutes, ff.110-111, Jamaica National Archives, Spanish Town, Jamaica; “Extract of a letter from Don Juan Francisco del Valle to the Marquis de Monteleon, March 18, 1716,” CSPCS, Jan. 1716 – July 1717, item 158i; “Declaration of Antonio Peralta,” Consulado de Cadiz, legajo 853, AGI; “Declarations of Pedro de la Vega.”
• https://en.wikipedia.org/wiki/Henry_Jennings