It’s safe to say that Prince Rupert of the Rhine is one of the unique characters of the 1640s and 1650s. With his long hair, youthful looks, and dashing deeds not only was he the archetypal “Cavalier” but more than 360 years ago he concocted one of his boldest plots in one of the strangest moments of the English Civil Wars…
Prince Rupert’s naval career began during the Second Civil War of 1648 when he joined Charles, Prince of Wales in an unsuccessful naval exedition using Parliamentarian ships that had defected to the Royalists during the naval revolt of 1648. Retreating to the neutral port of Helvoetsluys in the Netherlands, Rupert – now appointed admiral – was blocked until November 1648 when he began a new career as a privateer, raiding English merchantmen to help raise funds for his uncle Charles I’s soon-to-be-literally-cut-short cause.
His fleet sailed to Kinsale in southern Ireland in January 1649, Rupert travelling on his flagship, the 40-gun Constant Reformation. Here he learnt of his uncle’s execution and swore revenge on the regicides and went full-blown pirate – causing enough of a problem that the Commonwealth navy prepared a larger fleet to sail against him. Rupert’s ships were blockaded by the Irish Sea squadron, which included amongst its commanders newly-appointed general-at-sea Robert Blake, with whom Rupert would ‘enjoy’ a tempestuous relationship over the coming year.
After Cromwell’s invasion of Ireland in 1649, Rupert’s position was increasingly threatened. But earlier in the year he had written to King John IV of Portugal, asking permission to base his ships at Lisbon if he should be forced to leave Ireland – John responded favourably and, in September 1649, when bad weather, repairs, and other duties reduced Blake’s blockade to just five vessels, the prince made a break for it with his seven best ships.
Privateering along the way bolstered his numbers but although King John was sympathetic to Rupert’s cause, his chief minister – the Count de Miro – feared that open support for the English Royalists might damage Portuguese trade and also encourage the Commonwealth into an alliance with Portugal’s chief enemy, Spain. Despite hostility and obstruction from the local mercantile community, Rupert and his younger brother, Prince Maurice, threw themselves into a PR campaign, schmoozing with King John and Lisbon nobility, and winning the support of the local clergy.
But the party would soon be over. In early 1650, England’s new Council of State denounced Rupert as a pirate and commissioned Blake to destroy the Royalist squadron. Blake sailed from Portsmouth in March 1650 with a powerful fleet of fifteen ships. They arrived at Cascaes Bay at the mouth of the River Tagus on 10 March 1650 and Blake immediately demanded the use of Lisbon harbour and Portugal’s co-operation against Rupert’s pirates – his answer was warning shots fired from Portuguese forts when he tried to sail up the river.
Diplomatic negotiations resulted in Blake anchoring just two miles downriver from Rupert’s ships and a standoff ensued as each side competed for support from the Portuguese king.
As negotiations proceeded, the Portuguese agreed to allow sailors from both sides to come ashore and use the harbour. You can imagine what happened – cross Casablanca mixed with Pirates of the Caribbean and you’ll have something close. With men from both sides frequenting the same taverns, brawls inevitably broke out between crews of the rival fleets.
But the oddest part of this already-strange stand-off were the tit-for-tat assassination attempts…
After an alleged ambush attempt by Commonwealth sailors on the princes during a hunting trip, Rupert retaliated by designing an ingenious booby-trap that nearly sank one of Blake’s main warships.
On 13 April 1650, Rupert dressed a member of his crew as a merchant and employed two locals to row a small boat carrying, amongst other goods, a large barrel towards the Commonwealth vessel Leopard. Small fleets of trading boats often thronged around the opposing ships to sell provisions, and so this aroused no concern from the Leopard’s crew. When they arrived, the disguised crew member entered into discussions with the ship’s quartermaster to sell the “barrel of oil” and, after agreeing a price, the barrel was being hoisted aboard.
But the crew became suspicious and the men were seized. The barrel was found to contain a large explosive-filled shell, a string leading from the “merchant’s” boat was attached, through a bunghole, to a pistol. Pulling the string would have fired the pistol and ignited a fuse. It was clear that the plan had been to trigger the device once it had been taken aboard and, potentially, sink the ship.
It was a typically audacious plot by Prince Rupert, who maintained a lifelong interest in the sciences, but it did nothing to break the deadlock. King John refused to allow Blake to attack Rupert’s ships while they were under Portuguese protection, and Rupert could not risk leaving Lisbon harbour with the powerful Commonwealth fleet nearby. Eventually, Blake attacked and captured an inbound Portuguese fleet carrying a rich cargo of 4,000 chests of sugar from Brazil, a major blow to the Portuguese economy, and King John was forced to insist that Prince Rupert’s squadron leave Lisbon. Taking advantage of Blake sailing to Cadiz to resupply, Rupert escaped.
For more on this extraordinary episode of the English Civil Wars, we recommend John Barratt’s Cromwell’s Wars at Sea (Barnsley, 2006) as well as Frank Kitson’s Prince Rupert, admiral and general-at-sea (London, 1998).