Captain Jennings Causes Chaos

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By Adrian Tinniswood | Published in History Today Volume: 60 Issue: 5 2010

Early 17th century England saw the emergence of pirates, much romanticised creatures whose lives were often nasty, brutish and short. Adrian Tinniswood examines one such career.

The execution of a pirate at Execution Dock in Wapping, London

The execution of a pirate at Execution Dock in Wapping, London

Where are the days that have been ... when we might do what we list, and the law would bear us out in it? When the whole sea was our empire, where we rob at will?’

(Andrew Barker, A True and Certaine Report of ... two late famous Pirates, 1609)

One consequence of the Somerset House Conference, which brought an end to the ‘long and most cruel ravage of wars’ between England and Spain in the summer of 1604, was the cessation of privateering. This legal variant on piracy, whereby private individuals carrying letters of marque from their government were permitted to seize goods and ships belonging to an enemy, was big business. In the late 1590s at least 85 privateers were operating out of London and the south coast ports and the prizes they brought home accounted for between 10 and 15 per cent of English imports.

Eager to show himself the strong, authoritative Rex Pacificus that he so conspicuously was not, James I quickly issued a stream of strident proclamations outlawing privateering by his subjects and promising the direst penalties against those who persisted in harassing Spain and its allies. His words had the effect of pushing hundreds – possibly thousands – of English sailors into outright piracy. Resentful of the fact that James ‘hath lessened by this general peace the flourishing employment that we seafaring men do bleed for at sea’, as one put it, they adapted to their change of status and continued as before, the only difference being that many no longer felt the need to confine themselves to robbing the Spanish.

One of these Jacobean privateers-turned-pirates was Captain John Jennings. He wasn’t famous; there were no broadside ballads written about his exploits and, as far as I know, the full story of his brief but eventful career has never been told until now. He wasn’t even particularly good at piracy: his judgement was poor, his leadership skills were worse and his single-minded determination to indulge himself proved to be his undoing. But his tragi-comic career offers an intriguing sidelight onto the chaotic and arbitrary world of Jacobean piracy.

Nothing is known of Jennings’ early life except that, by his own account, dictated shortly before his death, he was from childhood ‘wholly addicted to martial courses, especially in the manly resolution of seafaring men’. He duly went to sea and, after a ten-year privateering career in which he bore arms for England, then Spain, then Holland, he finally tipped over into downright criminality in 1606, capturing a French merchant ship in the Channel and killing her entire crew. While the French ambassador in London demanded his immediate arrest, Jennings set sail south to Safi on the Atlantic coast of Morocco.

Jennings and his crew spent the late autumn and winter of 1606-7 at Safi, sailing out the following spring and returning at intervals with prizes ‘which amounting to so great a sum, it is incredible to report’, he later said. ‘I will only satisfy you that the most part was consumed in excess.’ He worked together with another Englishman, Gilbert Roupe, who had just relocated from Tunis, a favourite base for pirates since the beginning of the century, when the Tunisian bey, ‘Uthmân, began to establish the city as one of the most important international centres of piracy on the Barbary Coast. Why Roupe was in Safi we don’t know, although the prospect of easy pickings in the busy shipping lanes leading through the Straits of Gibraltar probably played a part in his decision.

Towards the end of 1607 the first in a string of disasters struck the partners when Roupe’s ship sprang a leak off the Isles of Scilly.‘ Captain Roupe and his company were compelled to come aboard of mine,’ said Jennings, ‘and his ship sunk immediately after.’ Uncomfortable but undaunted, the pirates set a course for south-west Ireland, wreaking havoc as they went. They took an English merchant ship, the John Evangelist off Scilly and a few days later captured a French vessel ‘laden with brass and other rich commodities’. Both required a prize crew, easing the overcrowding on Jennings’ ship; but neither suited Roupe as a decent replacement for the ship he had lost and both were sold along with their contents when the pirates put in at Baltimore, County Cork in early December 1607. The men spent the winter there, negotiating with local merchants over the sale of their stolen goods, disposing of their prizes and refitting their ship.

The townsfolk of Baltimore were known to be sympathetic to pirates, especially those with plenty of money to spend. One local woman proved so sympathetic that when spring came Captain Jennings offered her gold and promises and ‘so far prevailed with her, that he won her to spend her company at sea with him; and so hoisting sails, away they depart’.

The voyage was not a happy one. Roupe was still without a ship of his own and he and his crew had to sail with Jennings. They narrowly escaped capture by one of the king’s ships, which was waiting for them outside Baltimore harbour. They then got into a savage fight with two Spanish vessels and, with their own ship badly damaged, ten or 11 crewmen killed and another 20 hurt – including Jennings himself – they were forced to cut their losses and break off the engagement.

Some of Jennings’ company argued that this humiliation was ‘a just judgement of God against them, in suffering their captain to bring his whore aboard and there to wallow in his luxury’. Others asked how come their captain could have a woman aboard and they couldn’t? Gilbert Roupe, with an eye to usurping Jennings’ command, quietly egged them on until, at last, a group of seamen burst into their captain’s cabin and, paying no heed to the fact that he was actually in bed and in the arms of his Irish mistress, began to lecture him on his loose morals.

Jennings’ reaction was to pick up a truncheon and hit the nearest crewman over the head. Then he charged at the rest and cleared them out of the cabin, shouting ‘Captaine Roupe, will you suffer me to be thus taunted and abused?’ But Roupe was curiously slow to come to his aid and the angry sailors chased the unfortunate Jennings out of his cabin and into the ship’s gun room, where they locked him up.

The mutineers offered command of the ship to Roupe and he accepted. But, as the days lengthened on the voyage southwards to the safety of Morocco, they began to have second thoughts. Their ex-captain was a hard, self-centred man; but Roupe turned out to be worse and he favoured his own crew over them. Jennings, who was now allowed the liberty of the ship (although not, presumably, the liberty of his mistress, who disappears abruptly from the story at this point), worked hard to regain their trust. But by the time the pirates caught up with a French fishing boat off the Portuguese coast and Roupe gave the order to board her there were deep divisions between the two crews – so deep that while Roupe’s company stormed the French vessel, Jennings persuaded his own men to hold back. Roupe offered Jennings the command of his ship again and, after some awkward moments, the two captains were reconciled. They agreed to sail back to Ireland together to sell their plunder.

There was no uniform moral code among Jacobean pirates, but there was a hierarchy of scruple. The more principled pirates confined themselves to robbing Spain and its allies. Others maintained a toe-hold on the moral high ground by robbing everyone but the English. A third group – the group to which Jennings and Roupe belonged – would take anything they found afloat. Their contemporary, the powerful pirate Peter Easton, caused panic in the financial markets in 1610 when he announced that he regarded Englishmen as legitimate targets, ‘no other than as Turks and Jews’.

Worst of all, in the eyes of English society at least, were the ‘runnagates’ who turned Turk and settled permanently in one of the Islamic states along the Barbary Coast: Morocco, Algiers, Tunis or Tripoli. These men customarily joined a ta’ifat al-ra’is, one of the guilds of corsairs which engaged in exactly the kind of state-sanctioned privateering outlawed by James I. Only now they were crusaders against Christendom, warriors ‘who went on the sea jihad and found fame’, in the words of the 17th-century Algerian chronicler Ahmed Mohammed al-Maqqari.

It is impossible even to guess how many English pirates converted to Islam, but judging by the uproar caused in England when the notorious pirate John Ward turned Turk in 1610, it was a relatively rare event. The news of Ward’s conversion met with ‘the great indignation of the whole nation’, according to the Venetian ambassador in London. Clergymen in their pulpits thundered that Ward would end his days in drunkenness, lechery and sodomy in his opulent Tunisian palace, while congregations wondered idly if drunkenness, lechery and sodomy were really such a bad way to go. The apostate was portrayed in verse and on the London stage as part-demon, part-Faustian anti-hero. Captain Jennings remained a rather conventional Protestant, although how he reconciled his religious beliefs with his piratical activities remains a mystery.

He and Roupe got back to Baltimore just after Christmas 1608, by which time they had acquired a Dutch prize of some 180 tons. Jennings sent four men ashore to spy out the lie of the land. None of them came back. (He found out later that three of them deserted; the fourth was found in a country lane with his throat cut.) After waiting for several days the captain put back out to sea, followed by Roupe and the captured vessel. Still looking for supplies and a market for his goods, they sailed round the coast to Broadhaven Bay in County Mayo and sent another reconnaissance party ashore. It was ambushed by soldiers as soon as it landed.

Nothing was going right for Jennings and he decided the time had come to give up piracy. But what was he to do? He might settle in Safi or Algiers or Tunis; or start a quiet new life in Cornwall or Connacht, hoping that no one would recognise him. Or he could ask the king to pardon him.

On January 23rd, 1609, Jennings anchored outside Limerick at the mouth of the Shannon and set out his terms in a letter to the Earl of Thomond, the governor of County Clare and the military commander in Munster. He offered to give up everything: his Dutch prize, his cargo of sugar, pepper, cinnamon, wool, soap and brass; his ordnance and ammunition; his cables, anchors ‘and all necessaries fitting a ship of her burden’. All he asked in return was a pardon for himself, Roupe and their company.

As with so much of Jennings’ career, his timing was unfortunate. Over the previous couple of months the government in London had come under increasing pressure to do something about the problem of piracy. Reports arrived from the West Country complaining that ‘merchants are daily robbed at sea by pirates’; the Levant Company sent petitions begging for naval support to protect them from corsairs based at Algiers; the Venetians lobbied for a general embargo on trading ‘to any ports where the pirates resort’.

As a result, on January 8th, 1609 James I announced sweeping measures designed to stamp out ‘the many depredations and piracies committed by lewd and ill disposed persons’. Pirates, he said, were ‘most hateful to his mind, and scandalous to his peaceable government’. This was just 15 days before Jennings asked for his royal pardon.

Unaware of these developments in Whitehall, Jennings came ashore in Limerick offering to negotiate directly with Thomond if the earl would provide a safe conduct pass and send two of his kinsmen aboard the pirate ship as hostages. Thomond agreed and for the next two weeks Jennings ‘rioted in pleasure and revelled in the town’ while he waited confidently for his pardon to arrive. He entertained one of Thomond’s sons and various other local gentry aboard his ship, brandishing the earl’s letter of protection and doling out all manner of gifts.

While Jennings rioted and revelled, the earl was having a discreet chat with Roupe. He had got wind of the differences between the two men and, since Jennings was the more notorious, he offered Roupe a pardon if he would betray his comrade. Roupe agreed; but some of the company remained loyal to Jennings and Thomond’s kinsmen were still held hostage aboard their ship.

The safe conduct pass was valid for two weeks and on the day it expired, ‘having feasted voluptuously with [the hostages] aboard, and drunk hard, [Jennings] out of his own motion made the offer unto them, that that night they should go with him and revel it ashore’. His men, who were more sober and more sensible than their captain, tried to dissuade him, but he would have none of it and he duly set off with the two Thomond hostages for a night out in Limerick.

Roupe and the other turncoats seized their opportunity and set sail. When the sun came up the next morning Jennings found himself hung over and hung out to dry. The hostages had escaped and after a brief fight the unfortunate pirate was overpowered by the earl’s soldiers and packed off to London for trial.

But as Jennings was passed from Limerick to Dublin, from Dublin to Chester and from there to London to await trial something rather curious happened. Debauched, violent, base-born and barely literate, he elicited sympathy and fellow-feeling wherever he went. The Earl of Thomond took pity on him and, mindful that he had nothing but the light doublet and hose he was wearing when he was arrested, gave Jennings £100 to defray his expenses. At Dublin Castle, where he was held for three months, he freely confessed his crimes ‘and pleaded for mercy since he came in voluntary’, which was stretching the truth a bit. Even so, the lord deputy, who had previously been adamant that Jennings must hang, changed his mind when the man was actually brought before him. His contrition, his insistence that he had always respected the king’s subjects (a downright lie) and the notion that he would better serve royal policy alive than dead convinced the lord deputy that the prisoner deserved that pardon. In the meantime, Jennings was allowed out to hawk and hunt in the Dublin countryside like a nobleman, on the understanding that he would return to his lodgings in the castle each night.

After Jennings reached the Marshalsea Prison in Southwark in May 1609 he continued to impress his captors and they continued to press the king for a pardon. He was kept in the Marshalsea until December, sitting around in summer, getting drunk with his fellow prisoners, having snowball fights in the prison yard in winter and reminiscing about his glittering career. ‘Faith, Captain Jennings, and how did you live when you were at sea?’ he was asked. ‘I rejoiced more to hear the cannon’s voice that bid me to fight, than the church-bell that called me to prayer,’ he replied. ‘I fought not as chickens fight, for their meat to sustain nature, but for store of gold, to maintain riot.’

Through it all he maintained an endearing and, as it turned out, misplaced faith in the future. He came to trial at the beginning of December along with 19 others, all of whom were charged with piracy. Three co-defendants were members of his own company. One was a Cork shoemaker who claimed he had fallen asleep aboard Jennings’ ship and woken to find himself at sea. He was found not guilty, unlike several others who came after him and pleaded exactly the same excuse.

And unlike Jennings. But even with a guilty verdict and a death sentence pronounced, he was sure he was not going to hang. The Earl of Northampton, Lord Privy Seal and Earl Marshal, personally asked the king to reprieve him. He would be more use alive than dead, argued Northampton. And the word in the taverns and alleys of London was that James I agreed.

Ironically enough, it was a fellow-pirate who was the death of Captain Jennings. In November Sir William St John in the king’s ship Advantage was patrolling the coast of County Waterford when he came across the pirate Richard Bishop and his crew in Ardmore Bay. There was a furious battle and by the beginning of December Whitehall was ringing with the news that Bishop’s crew had boarded the Advantage and killed St John.

The reports were greatly exaggerated: St John was back in action against the pirates the following spring. Nevertheless, it was the news that one of the king’s officers had been killed which hardened James I’s heart against Jennings and which, in spite of all the petitions and pleas for clemency, made him determined to see him hang.

Captain Jennings’ death possessed a nobility which his life so conspicuously lacked. On Friday December 29th, 1609 he climbed the scaffold at Execution Dock in Wapping, directing a rousing final speech towards two loyal crewmen who waited their turn below:

You fearlessly and venturously have followed me, your Captain, who have as bravely brought you off as I have boldly brought you on. Be not dismayed now to do the like, for where heretofore I have driven you through the footsteps of transgression on earth, I now wish you be all as resolv’d as I go before you the highway to my salvation in heaven, where we shall meet amongst the fellowship of angels.

Then he said a prayer, sang the first few verses of Psalm 51, ‘Have mercy upon me, O God, according to thy loving kindness’, and stepped off the ladder into eternity and into a small but well-deserved place in the history of piracy.

Captain Jennings Causes Chaos | History Today

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