Pirate Prince of the Caribbean: Rupert of the Rhine

by Cryssa Bazos

Prince Rupert of the Rhine
Public Domain via Wikimedia Commons

One of the most dashing and iconic figures of the War of the Three Kingdoms is Prince Rupert of the Rhine. The son of Frederick V, Elector of Palatine, and Elizabeth Stuart, daughter of King James VI of Scotland and I of England, he fought for King Charles I’s against Parliament. The force and swiftness of his cavalry charge usually struck terror in the Parliamentarians. To this day, portraits of Rupert still causes hearts to flutter.

While Rupert is mostly known as a Royalist cavalry commander, he did move the fight from land to sea around 1648, leading his own fleet against the Parliamentary navy. He started in the Mediterranean before skipping over to Ireland to support the Irish Royalists for a time. While Rupert sailed in the West Indies briefly in 1651 before returning to the North African coast, it was the period between May 1652 and December 1652 when he effectively turned Pirate Prince, sailing through the West Indies hunting for Parliamentarian ships.

Rupert's travels by Akhritov derivative work
Public Domain via Wikimedia Commons

Traveling the West Indies

When Prince Rupert left the North African coast and Cape Verde on May 9, 1652, he had in his fleet a total of six ships: the Swallow, his flagship; the Defiance, commanded by his brother, Prince Maurice; the Honest Seaman, captained by a man named Craven; the John, the Sarah, and a Cape Verde prize (name unknown).

It had been Rupert’s intention to seek Barbados, but their navigation was off, and on May 29th, they landed instead in Saint Lucia. There, his fleet was able to restock their water supplies and take on ample fresh meat in the form of wild hogs and wild goats. Over the next days, they sailed northward along the Leeward Isles and ended up in Martinique, where they received the poor news that Parliament was in possession of Barbados. Good thing he didn’t go there!

The problem, Rupert quickly realized, was that during the time that he spent exploring the African coast, Parliament had moved to establish their presence in the West Indies and shore up control of English colonies, especially those, like Barbados, who had Royalist leanings. Where he expected to be welcomed by fellow Royalists, he found himself in hostile waters. This made it harder for him to find safe harbour, and therefore, replenish supplies. But he wasn’t there for the beaches, so he resolved instead to be the hunter instead of prey, a Prince Pirate of the Caribbean on the lookout for Commonwealth and Spanish ships.

On the lookout for rich prospects, at the beginning of June 1652, Rupert’s fleet headed for Montserrat, an English colony known for its sugar plantations. Thanks to the sugar being in high demand, merchant ships were thick in the area. Rupert was like a shark streaming through waters teeming with fish. His strategy worked, and he managed to capture two English prizes, one loaded with a hold full of sugar. But it wasn’t without loss. During a heated exchange near Nevis, Rupert’s personal secretary was killed, as was the captain of the Defiance.

A pirate prince couldn’t spend all his days ravaging the Caribbean without trying to make a few friends. Around June 8th, Rupert’s fleet arrived at St. Christopher’s (St. Kitts) where he attempted to trade with the Dutch merchants in the town, but the English settlers threatened retaliatory measures against the Dutch if they assisted Rupert, including the confiscation of their goods. In response, Rupert anchored in the French controlled harbour and traded there briefly.

Rupert’s fleet continued northward to the Virgin Islands where he finally found a bit of respite. There, he established a temporary base and spent the next several weeks outfitting his ships and fortifying the harbour against the Spanish. Food supplies were poor and everyone, including Rupert, were forced on mean rations. At the end of August, several men had enough of the conditions. The last anyone saw of them, they were sailing toward the Spanish colony of Puerto Rico on a stolen pinnace.

This ended Rupert’s sojourn. He had hoped to wait out hurricane season in a sheltered cove, but with the defectors heading towards his enemies, with full knowledge of where to find him, he pulled up anchor and headed for Anguilla.

On September 13th, catastrophe struck in the form of a hurricane. This hadn’t been the first time that Rupert had encountered the power of a Caribbean hurricane. A year earlier, his fleet had encountered one. After three days of trying to keep her afloat, his first flagship, the Constant Reformation, was destroyed with the loss of all her crew (333 souls). Before she went down, Prince Maurice brought the Defiance close along the Constant Reformation to try to save his brother and as many crew members as they could, but conditions were too dangerous to launch a full-scale rescue. Rupert had resolved to stay with his crew and go down with his ship, and he would have, were it not for his men forcibly bundling him into the only boat and sending him across to the Defiance.

Now a year later, another storm was coming down hard on them. This hurricane was an absolute beast. Rupert’s Swallow ran before the storm for four days. They could barely see one end of the ship to the other, and they lost their mainsails. At the worst of the storm, the ship was being propelled toward jagged rocks, but in a last-minute reprieve, the wind shifted and steered them clear of the rocks. They survived, barely.

When the hurricane passed, Rupert realized the extent of the storm’s devastation: his fleet was lost, and most heart-rending for him, there was no sign of the Defiance. Rupert’s best friend, his brother Maurice, was lost at sea.

Prince Maurice
Public Domain via Wikimedia Commons

Four days, on September 17th, the Swallow limped into St. Ann’s in the Virgin Islands, and took on fresh water and supplies, which were scarce because of the hurricane. Everyone was on reduced rations and starvation was a real threat. Over the next week, they sailed south looking for supplies.

Rupert searched fruitlessly for word of his brother and the rest of his fleet. For years, rumours circulated of Maurice being sighted across the West Indies, from Puerto Rico to Hispaniola, but they amounted to nothing. The Defiance was never heard from again. The Honest Seaman was also lost, but there were a few survivors. Several months later, Captain Craven turned up in France.

The loss of his fleet spurred Rupert to recoup some of his losses. In early October, he returned to Montserrat and captured a small English prize and tried to pick off a Spanish ship but couldn’t catch her.

On October 10th, Rupert arrived in Guadeloupe where he received word that the English Commonwealth was now at war with the Dutch Federation over a trade dispute. More tantalizing, he learned that there were rich prizes in Antigua, another English colony.

At the end of the month, the Swallow arrived in Antigua, but instead of sailing into Five Island Harbour, he approached with uncharacteristic caution. Rupert sent an advance party of fifty men, led by Captain Holmes, to scale the hill where an embankment of guns protected the harbour.

Holmes and his men spiked the guns then gave the signal for Rupert to sail into the harbour to capture the two English ships anchored there. The Swallow fired on one of the ships and crippled her, but the other surrendered without resistance. For the next couple of days, while the English soldiers created barricades on the beach to prevent a Royalist landing party, Rupert plundered the crippled ship then set sail with his prize.

Rupert would stay only another month in the West Indies. On December 12,1652, the Pirate Prince of the Caribbean closed off this chapter of his life and headed back to Europe with far less than he had hoped to return with. But at least Rupert would live to see another adventure.

Further reading
Prince Rupert: The Last Cavalier, by Charles Spencer

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Cryssa Bazos is an award-winning historical fiction author and 17th-century enthusiast. Her debut novel, Traitor's Knot, was a Medalist winner of the 2017 New Apple Award for historical fiction, a finalist for the 2018 EPIC eBook Awards for historical romance, and a finalist for the RNA Joan Hessayon Award. Her upcoming novel, Severed Knot, was longlisted for the HNS 2018 New Novel Award. 

Connect to Cryssa through her Website, Facebook, Twitter (@CryssaBazos), or sign up for her Newsletter. Traitor's Knot is available through Amazon. 

The overshadowed brother

by Anna Belfrage

Rupert 

It is difficult to study the period of the English Civil War without encountering Prince Rupert of the Rhine. This handsome nephew to King Charles pops up here, he pops up there, one of his uncle’s most loyal and competent commanders. So often does Rupert appear one could be forgiven for believing he was King Charles’ only loyal nephew. That, however, is not true. Rupert had an equally dashing and loyal brother, Maurice.

Rupert and Maurice came from a large family. Their mother, Princess Elizabeth Stuart, had wed Frederick of the Palatinate back in 1613 and for a little while the newlyweds had also been King and Queen of Bohemia, a venture that ended rather disastrously when the Holy Roman Emperor, Ferdinand II, decided to oust the Protestant pretender from Prague. Whatever hopes Frederick and Elizabeth may have had of remaining on the Bohemian throne were ground to dust at the Battle of the White Mountain in November of 1620. (Read more about Elizabeth here)

Elizabeth

In effect, Frederick and Elizabeth thereby became homeless, a royal couple without a throne. Catholic forces had invaded Frederick’s hereditary lands so they really had nowhere to go. Must have caused some concern, especially as Elizabeth was a most fertile lady. Baby Maurice was born in 1621, the fifth of thirteen children. By then, the family was installed in The Hague, which is probably why the baby was named after the then Prince of Orange.  Some say Elizabeth named her fourth son after the brave and ferocious Prince of Orange because he too would have to grow up to be a soldier and fight for what he wanted.

A very young Frederick

In 1632 Frederick rode off to join the Swedish warrior king Gustavus Adolphus on the battlefield, hoping to enlist his help in regaining his hereditary lands. A not-so-successful meeting ended with Frederick deciding to return to The Hague, but along the way he sickened and died. Elizabeth was left with a huge brood (albeit somewhat decimated: three had already died) to raise. By all accounts, she was utterly devastated by the loss of her husband. Her brother, Charles I, offered her a home in England but Elizabeth refused. She had to stay on the continent and fight for the rights of her eldest surviving son, Charles Louis.

Charles Louis and Rupert

Our Maurice grew up in The Hague. Where Charles Louis and Rupert were shipped off to their English royal uncle for extended visits, Maurice was mostly kept at home by his doting mama. Maurice had a habit of partying too hard which did not please the upright citizens of The Hague, even less so when on one occasion Maurice ended up fighting a duel which led to the death of one of his assailants. Elizabeth decided it was time her son learnt manners and sent him off to Paris to study at the University. I’m not all that sure this worked – partying in Paris must have been much more fun than in The Hague- and two years later Maurice decided he wasn’t cut out for studies and went to join the Swedish Army instead.

Over the coming years, Maurice saw a lot of action. He distinguished himself on the field, was considered a brave and competent leader of men. He was only seventeen when he served at the Siege of Breda, a resounding triumph for the Protestant forces. He fought for years under the Swedish Field Marshal Johan Banér. By the time the English Civil War began, our Maurice was a very young but battle-hardened warrior, as competent as his much more famous older brother.

Maurice

King Charles welcomed Maurice to England with open arms. He needed commanders – loyal commanders – and in Rupert and Maurice he had two such men, experienced enough to be able to face the Parliamentarian forces. The older brother, Charles Louis, was, however, persona non grata at the English Court. Where both Rupert and Maurice were royalists to their core, Charles Louis found much merit in the Parliamentarian cause, going so far as to sign the Solemn league and Covenant in 1644. (As to why he did this, I imagine Charles Louis had his eyes on the bigger prize, hoping the Parliamentarians might enthrone him instead of his uncle. To give Charles Louis his due, though, he was utterly shocked when Charles was executed in 1649)

Maurice served his king capably and loyally. Often in the company of Rupert, he was dismissed as being nothing but his older brother’s shadow, a good-for-nothing that lacked the skills to act independently. This was not the case, and there are various occasions during the Civil War when Maurice’s command and personal bravery resulted in won battles.

No matter how bravely and effectively Maurice fought, his reputation in England was destroyed by the debacle of the Siege of Lyme in 1644. Prince Maurice had been in the west for some time, successfully regaining ground from the Parliamentarian forces until only Plymouth, Poole and Lyme remained under Parliamentarian control.

Maurice was ordered to besiege and take Lyme – a walk in the park according to the other royalist officers. Turns out it wasn’t. Not only was Lyme kept in food and water by Parliamentarian ships sneaking into its harbour, but it was defended by men who fervently believed in the Parliamentarian cause. Maurice’s mercenaries were not as passionate, and things weren’t helped by nature itself, steep cliffs making it difficult for Maurice to deploy his artillery. In desperation, Maurice ordered the town to be stormed. Didn’t work. He did it again. Didn’t work. By now, Maurice’s men were less than enthusiastic about the whole thing and when they had news of the Earl of Essex advancing to relieve the town, Maurice had no choice but to pull back.

Demoted and humiliated, Maurice still continued to fight for his uncle, now mostly under the command of his brother, like at the Battle of Naseby.  He was also with Rupert at the disastrous Siege of Bristol where Rupert had to give up. King Charles angrily accused his nephew of cowardice and borderline treason and ordered Rupert to leave his service—immediately.

Rupert wasn’t having it. Neither was Maurice. Somehow they made their way back to the king where Rupert demanded he be court-martialled for the events at Bristol. He was cleared of any duplicitous behaviour but the relationship between the king and his fiery nephew was permanently damaged – even more so when both Rupert and Maurice tried to make King Charles see he had no choice but to negotiate with the Parliamentarians.
“Over my dead body,” Charles likely said (most unfortunately, given how things turned out) but he grudgingly allowed the brothers to remain in his service which they did until they were exiled by the Parliamentary forces in 1646.

Maurice didn’t exactly twiddle his thumbs once he’d left England. He found a new army to serve, new battles to fight, joining the French in Flanders. But when big brother Rupert suggested he return to serve under him in 1648, Maurice eagerly did so, enamoured, no doubt, by Rupert’s plans to crush the Parliamentarian forces at sea now that most of the Parliamentarian vessels had defected to the royalist cause.

Things didn’t work out quite as intended, mainly because fighting at sea was a totally different animal than fighting on land, and neither Rupert nor Maurice had any experience in managing naval forces. Plus, of course, the Parliamentarian navy had one of the better admirals around, a Robert Blake who soon enough had Rupert’s fleet fleeing for its life, away from England, away from Europe.

By the time 1650 rolled in, Rupert and Maurice were down to six ships or so but determined to regroup and return in force to England, there to push the claim of their young cousin, Charles II. Their uncle was dead, beheaded no less, and the royalist cause had little going for it. There was no money, no men, no leadership. It was Rupert’s hope that his ships would be able to sort the money issue by resorting to piracy, and for a while there things went rather well. Until a storm sank one of the ships and most of the treasure. Maurice almost drowned in the debacle but was pulled to safety at the last moment.
 
A short-lived reprieve as it would turn out. In 1652, the little fleet was hit by a hurricane in the West indies and one of the ships went down. This time, Maurice went down with it and no matter how his brother searched for him, he was never found. A devastated Rupert returned home to Europe. For years, he held out hope that Maurice had somehow survived, but Maurice never did reappear, stuck no doubt in a very watery grave somewhere in the Caribbean.

Maurice

Maurice was thirty-one when he died, a veteran of military campaigns on the Continent, in England and at sea. He never married, left no children, and in the history books his life is forever overshadowed by that of the gallant and charming Prince Rupert. But Maurice was more than a shadow, as gallant and brave as his brother. And in my opinion he was also by far the handsomest of the two – but that is neither here nor there.

All pictures in public domain and/or licensed under Wikimedia Creative Commons

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Had Anna Belfrage been allowed to choose, she’d have become a professional time-traveller. As such a profession does not exist, she became a financial professional with two absorbing interests, namely history and writing.

Presently, Anna is hard at work with The King’s Greatest Enemy, a series set in the 1320s featuring Adam de Guirande, his wife Kit, and their adventures and misfortunes in connection with Roger Mortimer’s rise to power. And yes, Edmund of Woodstock appears quite frequently. The first book, In The Shadow of the Storm was published in 2015, the second, Days of Sun and Glory, was published in July 2016, and the third, Under the Approaching Dark, was published in April 2017.

When Anna is not stuck in the 14th century, she's probably visiting in the 17th century, specifically with Alex(andra) and Matthew Graham, the protagonists of the acclaimed The Graham Saga. This is the story of two people who should never have met – not when she was born three centuries after him.

More about Anna on her website or on her blog!