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Henry Middleton c1610.

Chester in 1600

Despite defeating the Spanish Armada in 1588, England faced ongoing difficulties. The economy was hit by a series of poor harvests and there was a heavy tax burden to support the wars with Spain and in Ireland. There was a major famine in Chester in 1598. The population increased and demand drove prices up while wages fell. The Spanish war affected trade in Chester and much business shifted to the French ports, but there were losses of ships due to the war and growth began to slow. The important wool export trade declined. A noted feature of the economy of the time were monopolies, where the right to trade in certain goods was only granted to particular parties.

Sir Henry Middleton (d.1613) merchant and sea-captain, was the second son of John Middleton of Chester, sheriff in 1570. Henry is said to have been born in the parish of St Peter and was one of at least nine children. Robert Middleton, sheriff of Chester in 1518, was probably his grandfather. In his will, Henry styles Sir Thomas Myddelton (lord mayor of London in 1613–14) as "my loving and good friend". Thomas' son, Sir Thomas Myddelton (1586-1666, ownwer of Chirk Castle) would play a part in the Cheshire campaign during the Civil War, and The Booth Rising. Henry died at Bantam, Java, on 10 Feb in 1613. The story of Henry and his brothers is at odds with that of other mariners of late Elizabethan and early Stuart Chester, who are usially described as being restricted to trade with Ireland and nearby parts of Europe.

The Middletons were well-established in Chester. Thomas Middleton and David Middleton had been sheriffs in 1512-13, Robert Middleton in 1518-19. Edward Middleton was mayor in 1523-4, and David Middleton (1496-1548: born at Chirk Castle?) mayor in 1538-9. A John Middleton was sheriff in 1270-1. A discussion of the complex relations between the Middletons of Chirk and Chester can be found in the report Paradise Lost. It was probably the money gained from the Far East voyages that enabled the family to leave Chester and move to Middleton Hall in South Wales - now the site of the National Botanic Garden of Wales.

The parish of St Peter was relatively small.

Formed in London on 31 December 1600, the East India Company's (EIC) first voyage departed on 13 February 1601. The flagship of the five-vessel fleet was "Malice Scourge", purchased from the Earl of Cumberland for £3700; he had initially asked for £4000. There was at first some reluctance on the part of the EIC to acquire the vessel:

  • "her burthen being so great, whereby the Tunage agreed uppon shallbe so greatly exceeded" but they relented "to the ende the preparation of the viage [voyage] be not hindred by restinge in uncertentie of shipping."

Originally chartered as the "Governor and Company of Merchants of London Trading into the East-Indies", the company rose to account for half of the world's trade during the mid-1700s and early 1800s, particularly in basic commodities including cotton, silk, indigo dye, sugar, salt, spices, saltpetre, tea, and opium. The company also ruled the beginnings of the British Empire in India. The first voyages were funded with individual sums being raised for each group of ships sent out and a joint stock company was only formed later.

The story of the Middletons is largely reconstructed from the work of Samuel Purchas (c. 1577 – 1626) who wrote several volumes of reports by travellers to foreign countries. Those concerning the Middletons are in Volume 8, Chapter 10. On the formation of the East India Company, Richard Hakluyt had been appointed historiographer, and their historical and geographical documents were subsequently placed in his custody. He thus had charge of the journals of all the East India voyages from 1600 to the date of his death in 1616. In about 1620, four years after Hakluyt's death, these journals came into the hands of the Reverend Samuel Purchas, having probably been made over to him for publication. Instead of printing them in extenso, Purchas resolved to epitomize his materials, and, in this form, he published them in four folio volumes, in 1625. No proper provision appears to have been subsequently made for the safe custody of these journals, and consequently those that remain of these priceless records of the past are in many cases defective, and a still greater number are damaged by damp and decay. Not only was information lost, but later writers generated or repeated many errors in accounts of the early days of the EIC.

Middleton and others of his family were to play an important part in the early days of the East India Company, but apart from a brief mention in Fenwick they hardly appear in histories of Chester. At the time of writing it is not possible to say exactly where in Chester the Middletons lived, although the family home most likely stood in the parish of St Peter.

Early Voyages

James Lancaster, privateer and trader, was given command of the East India Company's first fleet.

There were 128 shareholders incorporated under royal charter as "the Governor and Company of Merchants of London trading in the East Indies", with a capital of £72,000: the first governor was Sir Thomas Smythe. The early voyages of the company, from 1601 to 1612, are distinguished as the "separate stock voyages," because the subscribers individually bore the cost of each voyage and reaped the whole profits, which seldom fell below 100%. After 1612 the voyages were conducted on the joint stock system for the benefit of the company as a whole. These early voyages, whose own narratives may be read in Purchas, pushed as far as Japan.   The Dutch traders considered that they had prior rights in the Far East, and their ascendancy in the Indonesian Archipelago was indeed firmly established on the basis of territorial dominion and authority. In 1613 they made advances to the English company with a suggestion for co-operation, but the offer was declined, and the next few years were fertile in disputes between the armed traders of both nations. In 1619 was ratified a "treaty of defence" to prevent disputes between the English. and Dutch companies. When it was proclaimed in the East, hostilities solemnly ceased for the space of an hour, while the Dutch and English fleets, dressed out in all their flags and with yards manned, saluted each other; but the treaty ended in the smoke of that stately salutation, and perpetual and fruitless contentions between the Dutch and English companies went on just as before. In 1623 these disputes culminated in the "Amboyna massacre" where the Dutch governor tortured and executed the English residents on a charge of conspiring to seize the fort. Great and lasting indignation was aroused in England, but it was not until the time of Cromwell that some pecuniary reparation was exacted for the heirs of the victims. The immediate result was that the English company tacitly admitted the Dutch claims to a monopoly of the trade in the Far East, and confined their operations to the mainland of India and the adjoining countries.

The story of the Middletons is confined to the early period when the EIC was mostly concerned with the Far East. The initial lead captain of the company was James Lancaster, and the three Middleton brothers of Chester were at a level just below. At the cost of all three of their lives they made a major contribution to the early success of the East India Company which is hardly remembered in Chester today.

First Voyage

Middleton's elder brother, John, was also from Chester and both the vice-admiral of the the EIA's first expedition to the Far East and captain of Hector (300 tons, 108 men, 24 guns) when that vessel took part in the 1601 expedition to the Indies. Overall the small flotilla was under Captain James Lancaster in this first voyage fitted out by the company. The other ships being Ascension (260 tons, 82 men, 24 guns, Captain William Brand) and Susan (84 men, John Hayward). To these was added, as a victualler, Guest of 100 tons with 40 crew: this was probably a full-rigged pinnace. John was much concerned with preparations before the trip and appears many times in the minutes of what appeared to be a reasonably well-organised committee. John was one of those appointed to survey the ships proposed and surveyed "Susan", his list of the ships inventory is very detailed, down to the last frying-pan and unlike the other surveyors who start with masts, sheets and sail, he starts his list with 14 demi-culverins and 10 sakers followed by a list of shot and powder. It may be that this reflected John's opinion of their relative importance: new sails being easier to obtain.

Cononial posts in Sumatra and Western Java. The markings on the map show the conquests of Iskandar Muda, 1608–1637.

On John's recommendation, 10 Oct. 1600, Henry was appointed purser of the Malice Scourge, afterwards named the Red Dragon, which was engaged in Lancaster's expedition; but shortly before the fleet sailed Henry was advanced to be a "factor" for the voyage, and another purser was appointed in his stead. The purser's role was a relatively important one - being responsible for all administration and cargo as well as the relatively large amount of bullion being carried.

They replenished their provisions from a captured Portuguese vessel (Viana) en route, such piracy being justified being that Portugal and England were on opposite sides of the Anglo-Spanish War (1585–1604) and sometims opposed in the Dutch–Portuguese War (1602–1663. Much of the fleet was affected with scurvy by the time they arrived at Table Bay (modern South Africa) on 9 September. Lancaster had managed to prevent the sailors on his own ship from being so stricken by regularly dosing them with lemon juice, and he was forced to send members of his own crew to help man the other ships into the harbour. They stayed at Table Bay for seven weeks before departing, navigating along the eastern side of Madagascar. Since leaving England, they had lost more than a fifth of their c.500 crew complement across the fleet, but those that remained were now relatively fit and healthy. On 5th June 1601, the fleet arrived in the road of Aceh, on the northern end of Sumatra, where they found sixteen or eighteen sail of different countries, and John Middleton with four or five gentlemen were sent to see the "King", Ala-uddin Shah, who was delighted at the prospect of trade with the English, and granted them an exemption from customs dues as well as rights to establish a "factory" where "factors" could organise trade. However the pepper crop had failed in the preceding season and the goods then available at Aceh failed to even fill one of the ships. Moreover, the ships were carrying a cargo of woollen cloth and different kinds of metal (iron, lead and tin). The problem was that Sumatrans were not very interested in trading their precious spices for these goods - given the climate in Sumatra, wool (which the English considered a valuable export) seemed particularly useless to the natives.

At Aceh, in June 1602, Lancaster appointed Henry to Susan (formerly a Levant trader with 24 guns) as "captain and chief-merchant", and sent him to Pariaman half-way down the south Sumatran coast to try and procure a laduing of pepper and spices paid for in bullion. Lancaster decided that if his voyage was to be made a success, it must be by other methods than those of peaceful trade. The Company had, under the politic name of “reprisals,” given him a strong hint "to take such course therein as he shall think meet" with regard to enemies of the realm. He interpreted this as a sanction to join the Dutch in an attack upon the "Portugals". Whiie Henry was away Lancaster decided to target Portuguese vessels in the Strait of Malacca to increase his cargo. The mission was successful, a Portuguese carrack of 900–1,000 tons called São Thomé was captured. The vessel had sailed from San Thomé (now part of Chennai), and the goods of calicoes and other produce were transferred onto the English ships. Susan returned having obtained an acceptable cargo of some cloves and mostly pepper, and in December sailed for England, where Henry arrived on 21 June 1603. Red Dragon and Hector, travelled south to Java where they set up a "factory" at Bantam and eventually arrived back in England on 11 September 1603, but not with John Middleton who had died at Bantam shortly after his brother Henry and Susan had set sail for home. As the annals of the EIC record:

  • "We went on with our trade, so that by the 10th February, 1603, our ships were fully laden and ready to depart. In the mean time, Mr. John Middleton, captain of the Hector, fell sick on board his ship in the road. For, from the very first of our voyage, the general made it an invariable rule, if he were ashore, that the vice-admiral must be on board, and vice versa, that both might not be at one time from their charge. Hearing of his sickness, the general went aboard to visit him, and found him much weaker than he himself felt or suspected, which experience in these hot climates had taught our general to know; for, although Captain Middleton was then walking about the deck, he died about two o'clock next morning."

Despite its relatively short-lived existence, the English East India Company's trading factory at Bantam would prove to be fundamental in developing Britain's relationship to Asia and its European competitor empires. It represented the English muscling in on the power of the Portugese and more importantly the dominant Dutch in the Spice Islands trade. Bantam provided a trading hub that would allow teas from China, spices from the Philippines and pepper from the Indies to all be coordinated for shipping back to the lucrative European markets.

Second Voyage

On Lancaster's return, Henry Middleton was appointed to command the second voyage fitted out by the EIC, and on 25 March 1604 he sailed from Gravesend in Red Dragon, having also under his command Hector, Ascension, and Susan, but when they stopped at the Downs, it was discovered that they were forty men short of their complement, and so had to wait for the remaining men. There was then a rather farcical series of events where as the new crew arrived it was discovered that they would have suplus crew so some men were actually paid off and put ashore.

After touching at Maio, one of the Cape Verde islands, they sailed again on 26 April, but being becalmed in the doldrums, they did not sight the Cape of Good Hope till 13 July. Although in the former voyage Middleton had seen the value of lemon juice being doled out by Lancaster, he had taken no measures to provide his ships with it. The men had consequently suffered severely, and, contrary to the company's orders, the fleet was obliged to stop for a month at the Cape to get fresh produce which still contained vitamins.

On 19 Dec. they made the coast of Sumatra, and anchored at Banten near the east tip of Java on the 23rd, the men being, by this time, again at the last extremity of weakness. On the first voyage a number of men had been left behind at Banten to gather spices by trade so that the second voyage could collect them. These "factors" frequently suffered from ill-health and even madness, but there was enough of a store of goods awaiting loading that two ships could be sent home.

On 18 Jan. 1604–5, Middleton, in Red Dragon, with Ascension, went on eastwards towards the Banda Sea, while Hector and Susan were ordered home with cargoes of pepper. The men were at this time dying fast; twenty-six are named as having died on board Dragon between leaving Banten and anchoring at Ambon on 10 Feb. The island was at the time held by the Portuguese, but just at this time the Dutch seized the island, and so put an end to all chance of trade there.

After long debate and with much misgiving, Ascension and Dragon resolved to separate, the former going to the Banda Islands, the latter to the Moluccas. Banda was the world's only source of nutmeg and mace, spices used as flavourings, supposed medicines, and preserving agents that were at the time highly valued in European markets. To reach Europe they were previously sold by Arab traders to the Venetians for exorbitant prices. They sailed from Ambon on 18 Feb., and on 22 March after a tedious voyage Dragon got off Tidore, where the Portuguese had a settlement, and were supporting the natives in a war with their neighbours at Ternate, who were aided by the Dutch. Until the colonial era, cloves only grew on a few islands in the Moluccas (historically called the Spice Islands), including Bacan, Makian, Moti, Ternate, and Tidore, so these islands were important. However, Middleton's force was too insignificant to permit of his taking any part in the quarrel, which ended in the complete defeat of the Portuguese and the death of their commander, said to have been poisoned by his own wife.

The Dutch threw every possible obstacle in the way of the English trade; and though Middleton managed, here and there, to pick up some cloves, it does not appear that he had anything like a full cargo when, on 24 July, the Dragon anchored again at Bantam. Dragon sailed for England on 6 Oct., and on 19 December, standing in for Table Bay, sighted Hector in the last extremity of distress, almost all her men being dead. Middleton sent men on board to take her into the bay, where they stayed for a month, and where they were joined by Ascension. At some point Susan and her cargo had been lost: she is last listed as “Bantam 4 March 1605 – parted company from the Hector after three months, not heard of again”.

They sailed for home on 16 January, and, after touching at St. Helena, anchored in the Downs on 6 May 1606. Middleton's services were promptly recognised. He had pushed his voyage much further than the company had dared to order him, and, despite the loss of Susan the profits were very great. Sales from the combined accounts of the first two voyages realised a profit of ninety-five percent. Henry was knighted at Greenwich on 25 May 1606; and ten years later he was still described as "the thrice worthy general who laid the true foundation of our long desired Cambaya trade".

1607: David Middleton

A third brother, Captain David Middleton in Consent, appears to have been intended to accompany the third fleet under Captain William Keeling. But setting out on the 12th March, 1607, from Tilbury Hope, while Captain Keeling did not reach the Downs till the 1st April, Middleton either missed the other ships at the appointed rendezvous, or purposely went on alone. The Third Voyage of the East India Company (EIC) (1607-10) was the first to be organised after the Anglo-Spanish War (1585–1604). It was also the first English voyage to reach India, following the route established by the Portuguese nobleman and later viceroy of India, Vasco da Gama, in 1498. David Middleton made his entire voyage independently. While Hector (Anthony Marlowe) became the first English ship to enter an Indian port, David Middleton simply made a fast voyage in Consent to the Moluccas and back.

Map showing the locations of islands in the Moluccas and Banda Sea.

David was the younger brother of John and Sir Henry Middleton and in 1601 jointly commanded a voyage to the West Indies. His account of this early European voyage to the West Indies includes descriptions of Florida and Cuba. In 1604 he went to the East Indies with his brother Henry, on the second voyage as second captain of Red Dragon, and is mentioned as having conducted the negotiations with the "native kings" of Ternate and Tidore. He returned with Henry in May 1606. On 12 March 1606–7 he sailed from Tilbury as captain of Consent, one of the ships of the third voyage under William Keeling. The trip was (by the rather poor accounts provided) rather uneventful although the narratives of visits to places such as Buton are of interest. The Sultanate of Buton ruled over the island from the 14th until the 20th century. Unlike other kingdoms and sultanates in the region, the Sultanate of Buton was a constitutional monarchy. The constitution was written and named Murtabat Tujuh. This constitution was formalized by Sultan La Elangi (1597-1631) and did not change much until sultanate was abolished. The king apparently visited the ship.

The narrative of the voyage contains the following passage which illustrates the interaction of these two quite different cultures from opposite ends of the world:

  • "We stood for Booton with a small gale, which at night died away, so that we had to drop anchor in 22 fathoms, not willing to drift to leeward with the current; and next morning we again weighed and stood for Booton. The 22d, about ten a.m. our purser came on board, having been sent on shore the night before, and brought with him some cocks and hens. He told us that the Indians had carried him to a king, who was glad to see him, having never before seen any Englishmen.[269] At his first coming to the king's house, he was carousing and drinking with his nobles, all round where he sat being hung with human heads, whom he had recently slain in war. After some little stay, the purser took his leave, and lay all night on board the caracol. This night we anchored in 20 fathoms, in a strait or passage not half a mile wide. The 23d, in the morning, we again weighed, and, having very little wind, our long-boat towed us through the straits, and as the tide was with us we went ahead a-main; so that by eleven o'clock a.m. we were in sight of the town of Booton, and came to anchor in 25 fathoms, about a mile and a half from the town, where we waited for the king to come on board, but he came not that night. We sent, however, our boat on shore, and bought fresh fish for our company. The king came up under our stern about one p.m. of the 24th, having with him some forty caracols, and rowed round us very gallantly, hoisting his colours and pendants; after which they rowed back to the town, and our captain saluted them with a volley of small arms and all his great guns. He then caused [the crew to] man our long-boat, and went ashore to the town of Booton, accompanied by Mr. Siddal and others. The king saluted our captain on landing, both with small arms and ordnance, saying that his heart was now contented, as he had seen the English nation, promising to shew our captain all the kindness in his power. The captain humbly thanked him, and took his leave for the present, coming again on board. Next morning, the 25th April, we weighed anchor and stood farther into the road, anchoring again in 27 fathoms within half a mile of the shore. This morning there came on board a Javan nakhada, or ship-master, who had a junk in the roads laden with cloves, which he had brought from Amboina, with whom Mr. Siddal our factor talked, as the Javan offered to sell all his cloves to our captain. This day the king invited our captain to dine with him, begging him to excuse the homely fashion of their country. The meat was served up in great wooden chargers, closely covered up with cloths, and the king with our captain and Mr Siddal dined together, where we had great cheer, our drink being Irea-pote, which was sweet-tasted and very pleasant, the king being very merry. After dinner we had some talk about the cloves which we proposed to purchase; and the king promised to come next day on board himself or to send some of his attendants, to examine our cloth. The captain then gave the king great thanks for his kindness, and went on board. The 26th, the king's uncle came off to see our ship, and was kindly entertained by the captain. The king's brother came afterwards on board, and remained to dinner with the captain, and after took leave. We expected the king, but he came not that day, sending his son and the pilot to view our cloth, which they liked very well. The king and his son came on board on the 27th, and dined with the captain, who gave them good cheer; and the king being very merry, wished to see some of our people dance, which several of them did before him, when he was much pleased both with our dancing and music. At night the king's uncle sent our captain four fat hogs. The 28th, the king of another island near Booton came in his caracol, accompanied by his wife, to view our ship, but could not be prevailed on to come aboard. Our ship being now laden with cloves bought of the Javans, our captain bought some slaves from the king; and while we were very busy this night, one of them stole out from the cabin and leapt into the sea to swim ashore, so that we never heard of him more. Next morning the captain sent Augustine Spalding, our Jurabossa, to inform the king of the slave having made his escape, who presently gave him another. May 3rd, we proceeded for Bantam, saluting the town of Booton at our departure with three guns."

Keeling had taken Hector to try to open trade in the Banda Islands, but he was unsuccessful and was forced to return to Bantam. From there, he departed in October 1609 heading back to England with a cargo of pepper, arriving in May 1610. Overall, the Third Voyage was immensely lucrative for the English, returning a profit of 234%.

Fifth Voyage

The EIC's fourth voyage departed in 1608 and was almost a complete disaster. The two ships, Ascension (Alexander Sharpeigh) and Union (Richard Rowles), were separated by a storm after leaving Table Bay. Sharpeigh was detained at Aden and had to pay a large sum to get free. He later wrecked his ship at Surat and the second ship was also lost.

One ship only, Expedition (300 tons, previously the "Bonaventure") belonging to London, appears to have been employed in the fifth voyage which was again commanded by David Middleton, whose own narrative of the journey survives. The following are extracts as provided by Purchas:

  • "We set sail from the Downs the 24th April, 1609, in the Expedition of London, and had sight of Fuerteventura and Lançerota the 19th May; and with the winds sometimes fair, sometimes foul, we arrived at Saldanha bay the 10th August. Making all haste to wood and water, we again sailed the 18th August, and arrived at Bantam on the 7th December, missing Captain Keeling very narrowly, who must have passed us in the night, or we must surely have seen him. I made all possible dispatch, both by day and night, to get the iron ashore, and would not even stop to set up our pinnace."

Foul winds compelled him to bear up for Banda, but there the Dutch governor told him plainly that to permit him to buy a nut there was more than his head was worth. He believed that they intended to seize or burn the ship, till he showed them that he was prepared to fight if attacked.

  • "We got sight of the islands of Banda on the 5th February, and made all sail to get near before night. When near, I sent my skiff to procure intelligence from some of the natives, who sent me word that the Hollanders would not allow any ship to come into the roads, but would take all our goods, if they were such as they needed, and pay for them at their own pleasure. They said, likewise, that when any junks happened to come there with vendible commodities, they were not permitted to have any intercourse with the people; but were brought to the back of the Dutch castle, within musket-shot of their cannon, no one being allowed to set foot on shore, under penalty of being shot. There were, as was said, fifteen great junks detained under the guns at this time. "

At Ceram, after some negotiation, he obtained a full cargo of nutmegs and mace, but then had a narrow escape from cannibals:

  • "When out of sight of Pulo-way, it came on to blow a heavy storm, so that I had to scud before the wind and sea to save our lives; yet, thank God, we got sight of Ceram, and kept her right afore the sea, but clean from the place where our ship lay; and on nearing the shore the sea did break so aloft, that we had no hope of getting safe on shore. Night being at hand, we strove all we could to keep the sea till day; but as the storm increased, we had no remedy for our lives but attempting to get through the surf over a ledge of rocks. This we did, but durst not leave the boat, lest we had been dashed in pieces on the rocks. Next morning we got her on shore, being brim-full of water, and everything we had washed out. Immediately afterwards, the blacks came and told us we must go to sea again instantly, if we valued our lives, for we had landed in the country of the cannibals, who, if they saw us, would come and eat us. They said nothing could ransom us from them if once taken, and especially because we were Christians they would roast us alive, in revenge for the wrongs the Portuguese had done them. Our blacks added, if we would not put immediately to sea, they would go and hide themselves, being sure the cannibals would be at the water-side as soon as it was light"

On his way back to the westward he foiled an attempt of the Dutch to intercept him, and having refitted at Bantam sailed thence on 16 November and returned safely to England in the summer of 1611.

Sixth Voyage

Henry Middleton's expedition to the Red Sea as re-told by the Victorians.

In 1610 Henry Middleton was appointed to command the sixth voyage set forth by the East India company, and sailed from the Downs on 4 April in Trade's Increase, having in company Peppercorn, commanded by Nicholas Downton, and Darling. Also with this fleet was Nathaniel Courthope (born 1585;– died c. October 20, 1620) (sometimes written Courthopp) an English East India Company officer. Giles Milton's book "Nathaniel's Nutmeg: Or The True and Incredible Adventure of the Spice Trader Who Changed the Course of History", gives an account of the struggle for possession of the Banda Islands which Courthope was involved in. The voyage launched the Company’s first two custom-built ships. Actively contemplated since 1607, the vessels were Peppercorn, a modest 340 tons, and the massive Trades Increase, at nearly 1,300 tons the greatest merchant vessel built in Jacobean England.

The voyage out was comparatively fortunate, and there was no exceptional sickness when, on 7 November, they arrived at Aden. The events which followed in the Red Sea and the Indian Ocean can be read several ways. The Victorians retold them for schoolboys as a tale of a heroic English trader. They could also be understood as the acts of a pirate. Some modern historians consider the voyage a complete disaster.

Aden was an ancient port and was famously the destination of one of the "Ming Treasure Voyages". It was ruled by the Ottoman Empire between 1538 and 1547 and between its capture in 1548 and 1645, hence the references to "Turks" in the narrative. In 1609 Ascension had been the first English ship to visit Aden, before sailing on to Mocha during the fourth voyage of the East India Company. Leaving Peppercorn at Aden, Middleton, with Darling, also went on to Mocha; but in entering the roadstead, in charge of a native pilot, Trade's Increase was run ashore, and much of her cargo and stores had to be landed before she could be floated off. The governor, or aga, received Middleton and the merchants with every appearance of friendship; but a few days later, 28 Nov. when a large working party was on shore, he suddenly attacked them, killed eight in the scuffle, and made prisoners of Middleton and the others, to the number of fifty-nine. He then attempted to seize Darling, which was lying close in shore; but in that the "Turks" were repulsed with heavy loss, some say with a single survivor. For more than three weeks the prisoners were kept at Mocha, heavily ironed; they were then sent to the bashaw at inland Sinan (Sanaa), where they were more humanely treated and allowed to communicate freely with the ships. Middleton and his crew must have been among the first Englishmen to penetrate this part of the Arabian peninsula.

Downton, who had arrived from Aden in Peppercorn, proposed making reprisals on the "Turkish" and Indian trading vessels, but Middleton restrained him, fearing that "it might prove prejudicial to him and his company." The bashaw, he said, had promised that they should all be set free at the coming of the westerly winds; if he suspected any breach of faith, he would make his escape. And when he learnt that a fleet of galleys was expected from Suez, and that the aga was negotiating for the hire of some of the larger country ships which Downton had allowed to come to Mocha, Middleton, on 15 May 1611, with fifteen of his men, did make his escape, got on board Darling, and sent orders to Downton to join him at once with the other ships. A more detailed account of the escape is given in "Natheniel's Nutmeg".


Henry then, by a strict blockade of the port, compelled the "Turks" to send back all the men who remained in captivity, and to restore the goods which had been seized on shore, or to pay compensation for the loss, and after refitting at Socotra, he went to Surat (this was before the British established their first factors there in 1612), where he arrived on 26 Sept 1610. He found the place closely blockaded by a Portuguese fleet of eighteen frigates, which made communication with the shore difficult, and prevented fresh victuals or refreshments being sent off for the men who were suffering from scurvy. After some skirmishing the prohibition to trade was partially withdrawn; but the governor was in too great dread of the Portuguese to receive the English with any appearance of friendship. He refused them permission to establish a factory, and after a stay of four months ordered them to leave. The merchants on shore were also ordered away, no time being allowed them to get in their debts. On 11 Feb. 1611–12 they sailed for Dabul, but neither there could any trade be done; and Middleton thought himself poorly recompensed by seizing a Portuguese ship of three hundred tons, and taking out of her what she had of value:

  • "cloves, cinnamon, wax, and bales of raw China silk—but a mite in comparison to the loss inflicted on the venture by the Portuguese."

From Dabul he went back to the Red Sea, blockaded Aden and the Straits of Bab-el-Mandeb, and seized several Indian ships by way of reprisals; but learning that the company's fleet of the year (the eighth voyage), under the command of John Saris, with whom was Gabriel Towerson, had passed into the Red Sea, he went in and joined Saris at Assab. He then demanded from the "Turks" one hundred thousand pieces of eight as compensation for former injuries and insults, and would probably have forced them to pay but for an angry quarrel between him and Saris, partly about the division of the spoil, and still more, it would seem, about their precedence.

c. 1700 Dutch map of the Arabian peninsula and environs, published by Vander Aa. The title of the map refers to the sixth voyage of Sir Henry Middleton on behalf of the East India Company, and shows his course. The map shows the Arabian peninsula in full, Abyssinia, the Horn of Africa, coastal Persia, and West India. Towns, rivers, and mountains are all shown.

The Victorian re-telling tries to give Middleton a completely different character:

  • For a time he did his best to carry on a peaceful traffic with the natives ; but finding himself thwarted therein, he boldly set his three vessels to attack the enemy´s twenty. He had such success that one of the Portuguese ships was sunk, another fell into his hands with a rich store of Indian goods, and the others were put to flight...Middleton returned to Mocha, and in excusable violation of his promise to its treacherous governor and people, set himself to punish them for the cruelties to which he and his men had been subjected a year before.

Finally Saris and Middleton accepted something like a third of their demand from the Indian ships; and so with much ill-feeling, and without "the usual courtesies", they separated in the beginning of August 1612, Middleton, with Peppercorn in company, going to Tecoa, on the west coast of Sumatra, where he joined Darling on 19 October. Saris would go on to visit Japan.

Far East

Downton relates that having bought a quantity of pepper at Tecoa, on examining it they "found much deceit; in some bags were small bags of paddy, in some rice, and in some great stones; also rotten and wet pepper put into new dry sacks." Towards the end of 1612 Middleton went on to Bantam in the Peppercorn, leaving Downton to follow in the Trade's Increase. In doing so the ship struck on an unseen rock, and when got off was found to be leaking badly. Downton returned to Tecoa and had her refitted as well as possible; but on joining Middleton it was decided that the ship could not go home till she had been careened. It was accordingly determined that Downton should take the Peppercorn to England, and he sailed on the homeward voyage on 4 February 1612 (OS) 1613 (N.S.). The voyage was one of difficulty and distress. Within three days after leaving Java Head half the ship's company were down with sickness. "He that escapes without disease," Downton wrote, "from that stinking stew of the Chinese part of Bantam must be of strong constitution of body." The passage home was tedious. Many of his men died, most were smitten with scurvy, he himself was dangerously ill; and the ship, in a very helpless state, unable by foul winds to reach Milford Haven, anchored at Waterford on 13 September 1613, and a month later arrived in the Downs. Peppercorn alone had made it back to England, but 19 members of the crew – those who had not already died or been killed in skirmishes – succumbed to scurvy, dysentery, and other diseases en route.

Trade's Increase was brought close to the shore, cables were attached to the masts and windlasses were used to pull the ship on to its side so that local labourers could replace rotting timbers and recaulk one side of the hull. Before the ship could be turned to repair the other half, though, the ship’s mainmast snapped and the vessel turned upright, killing as many as 500 Javan carpenters. Local Javanese people then probably set fire to the ship in revenge. Henry Middleton, the expedition leader, died on 24 May 1613, most likely from the disease that then carried off the remainder of the crew.

1614: David sails again

In May 1614 he sailed once more for the East Indies in Samaritan (bought from Nicholas Leate Jan 1614 for £3100, 75 crew, 453 tons), with Thomas and Thomasine under his orders, and arrived at Bantam on 14 February 1614–15. By this point the character of the East India Company appears to have been changing, with the minuites indicating a good deal more tension than before:

  • "Debate on the question of employing Capt. Middleton as general in the next voyage; many errors of his government ripped up, but he is nevertheless supposed to be the fittest person that can be thought upon to pursue trade either to Coromandel, Japan, China, the Moluccas, or any other places; he is opposed by Mr. Handforde as very unfit for government."

A full cargo was collected, and after sending the smaller vessels to other ports, Middleton, in Samaritan, sailed for England on 3 April 1615. But the ship was wrecked on the coast of Madagascar, and though it was at first reported that "passengers and goods were saved", the loss seems to have been total. The first report of Middleton's death reached the Company on 5 September 1617. No exact news was ever received, but he was registered as dead and his will proved on 18 April 1618. In his will, he names his wife Alice, sons Henry and John, daughter Elizabeth, and mentions a child not yet born, also his wife's sister, Jane Pullybancke. He names, too, his brother Christopher, his sisters and their children, several cousins and friends, the bulk of his property being left to his son Henry. Within three weeks of the announcement of the loss of Middleton's ship, his widow had remarried one Cannon. The family argued that they should get a share of the profits of the fleet in which he had sailed (Thomas also appears to have sunk) and on 6 October 1624 the court of directors had under consideration a letter in favour of Middleton's son.

  • "After much reasoning the court called to mind that the captain lost both ship and goods to a very great value, and therefore they gave it for answer that there is nothing due".

John Middleton had been on the first voyage (1601-1603) and it killed him. Henry survived the first (1601-1603) and second (1604-1606) voyages, but died on the sixth (1610-1613). David was on the third (1607-1609) and fifth (1609-1611), but vanished, presumed dead, on the thirteenth (1614). For most of the firdt decade of the 17th Century at least one of the three Middleton brothers had been engaged on a voyage to the East Indies.


Chester in around 1600 was a place of close-knit families with both religious tensions and important business connections, as well as rivalries. An understanding of the social structure can be obtained by careful study of the family and business relationships. However this is much complicated by some poor records or past interpretations of these records. Pedigrees, whether modern or older, need to be approached with considerable caution.

A family tree if the Middletons. The ones in green are the East India Company captains described in the text. Based on (the very readable) "Middleton : A Paradise Lost: In search of a garden before the Garden": Middleton Hall, Austin et al 2011.

It does not appear that Henry Middleton was married; the entries in the Calendar of State Papers (East Indies) to the contrary effect are certainly erroneous, as is shown by his will (at Somerset House), dated on board the Trade's Increase 29 March 1610, and proved by Alice, wife of David Middleton, on 22 June 1614. By this, his brother David, and David's son Henry, are left executors and residuary legatees. Mention is made of his brother Christopher (c. 1570-1639); of his three sisters, Katharine Tetlow, Margaret Burre, who has been erroneously named as his daughter, and Ursula Fawcet; his niece and god-daughter, Joan Burre; his cousins, John Haylin, Margaret Radford, Jane Hill, and her sister Sarah Hanmer; "my sister, Alice Middleton" (David's wife), and her daughter Elizabeth; "my sister, Margery Middleton" (Christopher's wife?); also Sir Thomas Myddelton (1550-1631) and his son Sir Thomas Myddelton (1586–1666) of Chirk Castle, (both were apparently merchant adventurers, with the older being a founder of the EIC), Hugh Myddelton, Captain William Myddelton, Captain Roger Middleton, and his brother William, and Robert Middleton. None of these last are described as relations; but in John's will dated 5 March 1600–1, proved by Henry 27 Oct. 1603, Hugh Myddelton is styled "cousin"; the sisters, Margaret and Ursula, were then unmarried, and two other brothers, Jarrett and Randall, are named, as well as his father, John. David in his will, mentions Robert Middleton (who was a merchant adventurer) also as a "cousin". Terms like "sister" as used at the time included sister in law, and "cousin" included various degrees of removal.

There are two contemporary 16th-century and related branches of the Middleton family, one of Denbigh and one of Chester. The Chester branch would inter-marry with the Bavands. Richard Bavand (Alderman, sheriff 1571-2, mayor 1581-2, 1600-1 and MP 1584) was a Chester merchant, described in 1589 as ‘ironmonger, vintner, mercer and retailer of many commodities’. He had considerable property in the city and its neighbourhood, and increased his estate by marriage to a local heiress. His mother was Margaret, daughter and coheiress of one of the Middletons of Chester.

The arms on Bishop Lloyd's House are very similar to those of the Company of Merchant Adventurers of London.

Chester had its own Merchant Venturers "guild" (founded in 1554) and it has been proposed that they may have been at some time based at Bishop Lloyd's House. In 1554 the Chester Merchant Venturers had been granted a charter by Queen Mary which gave them a monopoly of all trade to the continent, besides excluding retailers and all followers of manual occupations. The latter provision seems to have been disregarded almost from the beginning; the Chester Merchant Adventurers became a fairly comprehensive body despite some early disputes with the town corporation, and the charter was confirmed in 1559. The Chester Merchant Adventurers were involved both in extensive internal squabbles and a long term dispute with the Spanish Company prior to the Anglo-Spanish war (1585–1604). By the time these various arguments had been settled the war had actually started. We do not know how the various branches of the Middletons fitted into this squable.

John Middleton was one of the more important Chester merchants trading with the continent during the 1560s. In 1562, John was one of 8 merchants, who between them controlled more than fifty percent of the wine and iron which was shipped to Chester. In 1565-6, 27 merchants exported Manchester cottons to the continent, of these, only two men handled more than 2,000 goads, one of them was John. John’s wife Katherine, was the daughter of Chester Ironmonger, Thomas Bavand and his wife Margaret Myddleton. Margaret was the daughter of Robert Myddleton of Chester, who was the son of David Myddleton of Gwaynynog, the Great Grandfather of Sir Thomas Myddelton of Chirk. This then gives us the family link between the Llanarthne Middletons and the Chirk Myddletons.

Williiam Aldersey

Born in Chester (1578) to Ralphe Aldersey and Elizabeth Glegg. William Aldersey (younger) married Ann Whitley and had 1 daughter (Alice). He is not the same William Aldersley (MP} who obtained (together with Richard Poole and Richard Massey) the Chester Merchant Adventurers’ Charter which was granted in May 1554 by Queen Mary. Massey is thought to owe his establishment in the city to his marriage to a daughter and coheir of David Myddelton, mayor of Chester in 1523 and 1538. Aldersey (elder’s) leadership of the campaign was acknowledged by his being named the company’s first master. Similar movements were taking place at the time in London and other ports, and the Chester company encountered the same kind of opposition as did its counterparts from those whom they excluded. Its claim to promote the yield of customs must have rung hollow when in October 1554 Aldersey and other members were fined £100 for having paid no customs on consignments of leather, calfskins and wheat, and within a month its critics were writing to the city’s Members in the Parliament then in session about the pernicious consequences of the charter.

According to some sources Alice would marry the tenth John Leche of Leche House, however the pedigrees of the period are sometimes inconsistent, and there were several William Aldersey's. The information for the portrait of William Aldersey (younger, 1543-1616) on the Art Fund page relating to his portrait in the Grosvenor Museum (which hangs next to that of Bishop Lloyd) states that:

  • "He was a merchant ironmonger and so successful in overseas trade that he became a founding member of the East India Company in 1600."

This information is apparently taken from documents which were passed down through the Leche family. His name does not appear in the founders charter, but there is a "William Adderley* listed among the shareholders, mentioned as "William Adderley and Thomas Henshawe" (Henshawe could be the father-in-law of Chester MP Sir John Bingley). He subscribed at the rate of £240 per share during 1601, but (according to one source, others differ) the distributed profit on the first voyage by 1603 was nearly 300 per cent, and over all the East India voyages up to 1616 was never less than 220 per cent. Although the details are sometimes inconsitent between sources it does seem that there is an association between thr younger William Aldersey and the East India Company. It is almost certain that Aldersey would have known the Middletons.

Christopher Middleton

The remaining brother is Christopher, "for all were lost save he". Records from the Clergy Database contain references to a "Christopherus Middleton", residing in the Chester diocese, being ordained as a deacon in Chester Cathedral on 28th May 1580 and as a priest on 20th May 1582, and list his qualifications as an M.A. According to some records, on 24th February 1584 Christopher, was appointed vicar of Llanarthne by Bishop Marmaduke Middleton of St Davids - other records suggest that Marmaduke had already been deprived of his see by this time (for forgery), and had died in 1583. In 1611, Bishop Anthony Rudd appointed a successor to Christopher Middleton, and we may assume therefore that he had retired to his new estate, however his story remains somewhat confused and obscure. A Christopher Middleton, which may be same one, was the author of several works including:

One of the woodcuts from Christopher Middleton's work on swimming.

1) "A Short Introduction for to Learn to Swimme, gathered out of Master Digbies Booke of the Art of Swimming, and translated into English for the better instruction of those who understand not the Latin tongue, by Christopher Middleton," 1595. This was illustrated with woodcuts of persons swimming. It was a translation of the "De Arte Natandi libri duo", 1587, of Everard Digby. Christopher seems to have intended the work to be of serious benefit, but nowadays it makes for amusing reading:

  • "These directions are sufficient either for his entrance which is yet to learn, or for his which is already expert in this faculty. Now that is learning to swim, as we said afore, having waded in up to waist or somewhat higher, laying himself easily along upon the water with his belly downward, and striving as much as he can to hold up his head, and draw[ing] in his arms close to his breast, holding hands broadways together under his chin with the palms down; let pull his feet from the bottom and withal put forth his hands as far as he can and draw them in again as afore, and likewise his feet. Which double motion of hands and feet serve to this use: the one thrusteth him forward and the other keepeth up his body. And because it is a toil, something to learn how to strike right thus with his hands and feet as afore, let him either get someone to accompany that may by holding his hand under his chin keep him from sinking, else take two bladders, blow them full of wind and fasten them so together that he may have them to lie under his armholes, which will easily bear him up. And thus may he do till he hath perfectly learned to swim on his belly, as the picture following showeth"

2) "The Historie of Heaven: containing the Poetical Fictions of all the Starres in the Firmament, gathered from amongst all the Poets and Astronomers, by Chrystopher Middleton. Printed for him 1596". This is one of a clutch of similar works that appeared at the time, when there was a growing interest in astronomy both for scientific and navigational purposes;

Possibly the best explanation is that the Middleton's took the money obtained from the efforts of the three dead explorers and invested it collectively in the Middleton estate. Middleton Hall remained the home of the Middleton family for six generations, but by 1776 debts had risen to such a level that the estate had to be sold. However this was not to be the end of its Indian connection: William Paxton (1744–1824) made his fortune in India and he spent £40,000 on the Middleton Hall estate after he purchased it in 1789. Paxton built a new mansion, laid out ornamental gardens and woodland, and created ponds that were serviced by an elaborate underground network of water pipes. Paxton entered politics, sitting for election as MP which included (in his first failed attempt) payments for 11,070 breakfasts, 36,901 dinners, 684 suppers, 25,275 gallons of ale, 11,068 bottles of spirits, 8,879 bottles of porter, 460 bottles of sherry, and 509 bottles of cider.

The EIC in India

Sir James Lancaster’s 1591 voyage into the Indian Ocean was the first English attempt to reach the East via the Cape. Both its funding, and its armed shipping, was provided by Auditor Smythe and his Levant Company. Lancaster's voyage was disastrous in it’s loss of life and investment, but provided useful information about the Portuguese presence in the area. Lancaster himself, marooned on the Comoro Islands with the rest of his crew after he was shipwrecked during a cyclone, finally found his way home in 1594. Only one of Lancaster’s ships, the Bonaventure, made it back from the Indies, and that on a skeleton crew. The last survivors, five men and a boy, worked it home with its cargo of pepper, which they had earlier looted from a passing Portuguese ship.

Portrait of William Aldersey (mayor 1641-2 and 1613-4) from the Grosvenor Museum (purchased 2012). Painted in oil on an oak panel and dated 1615, the artwork is the earliest surviving portrait of any mayor of Chester. He died at Chester on 26 October 1616 and was buried in St Oswald.

In 1595 Captain Benjamin Wood tried his luck; all three of his ships, the Bear, the Bear's Whelp and the Benjamin, were lost and not an Englishman survived. Meanwhile Lancaster led a privateering expedition against Pernambuco and Recife in Brazil, aimed at seizing the cargo of a storm-damaged Portuguese carrack which had put in there on its way back from India. Unlike the East Indies voyage, this was (according to Hakluyt's account) highly professional in its conduct and very successful. Some sources state eroneously that this was after picking up a chance-met separate squadron under "Captain Henry Middleton". However Lancaster led an assault landing, seized the town and (some say with the assistance of a flotilla of Dutch traders who also threw in their lot with him) held it for several weeks and embarked the carrack's cargo along with local produce. It was this success and his earlier experience which led to his being selected for command of the East India Company's attempt.

In the commencement of its operations, the East India Company proceeded upon rather an anomalous plan for a great commercial company. Instead of an extensive joint stock for a consecutive series of operations, a new voluntary subscription was entered into among its members for each successive adventure. That of the first voyage was about £70,000. The second voyage was fitted out by a new subscription of £60,450. The third was £53,500. The fourth £33,000. The fifth was a branch or extension of the third, by the same subscribers, on an additional call or subscription of £13,700. The subscription for the sixth was £82,000. The seventh £71,581. The eighth £76,375. The ninth only £7,200. In 1612, the trade began to be carried on upon a broader basis by a joint stock, when £429,000 was subscribed, which was apportioned to the tenth, eleventh, twelfth, and thirteenth voyages. In 1618, a new joint stock was formed by subscription, amounting to £1,600,000.

For the early merchant adventurers, establishing a foothold in India was not an easy task. The East India Company did not establish its first 'factory' or permanent depot until 1619 (some sources say 1612), at Surat. In 1615, James I instructed Sir Thomas Roe to visit the Mughal Emperor Nur-ud-din Salim Jahangir (r. 1605–1627) to arrange for a commercial treaty that would give the company exclusive rights to reside and establish factories in Surat and other areas. In return, the company offered to provide the Emperor with goods and rarities from the European market. This mission was highly successful.

The opportunity for the British to greatly expand in India came in 1661, when Charles II married Catherine of Braganza and as part of his dowry gained Bombay from the Portuguese. Her 23 June 1661 Marriage Treaty gifted the islands to Charles II of England, along with the port of Tangier, trading privileges in Brazil and the Portuguese East Indies, religious and commercial freedom for English residents in Portugal, and two million Portuguese crowns (about £300,000), on completion of the marriage. The Islands of Bombay were regarded as a political and financial liability and were leased by Charles, to the English East India Company, on 27 March 1668, for a nominal £10 rent. King Charles II granted the EIC (in a series of five acts around 1670) the rights to autonomous territorial acquisitions, to mint money, to command fortresses and troops and form alliances, to make war and peace, and to exercise both civil and criminal jurisdiction over the acquired areas.

The company eventually came to rule large areas of India, exercising military power and assuming administrative functions. Company rule in India effectively began in 1757 after Robert Clive's victory at the Battle of Palashi and lasted until 1858 when, following the Indian Rebellion of 1857, the Government of India Act 1858 led to the British Crown assuming direct control of India in the form of the new British Raj.

Summary: East Indian Company and Chester

Giles Milton's book "Nathaniel's Nutmeg" gives more background on this period of Indonesian history, but says little on the connection to Chester.

The nautical history of Chester around 1600 is normally portrayed as one of gradual decline due to the progressive silting of the River Dee. Little attention has been given to the efforts of sea-farers originating from Chester when they sailed from elsewhere.

We can be certain that the three brothers from Chester were associated with the early voyages of the East India Company. It is less clear whether others from the city were involved. William Aldersley may have subscribed to the first fleet, but the evidence is unclear. The arms displayed on the frontage of Bishop Lloyds House may indicate that "Merchant Venturers" once met here, but the history is uncertain. Further research may reveal more substantial links between Bishop Lloyd's House and how the map of the world got largely painted red.

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