Chapter 2 – The Western Design

Oliver Cromwell | by Samuel Cooper

The expeditionary force in which Henry Morgan, known informally as “Harry,” enlisted as an ensign was part of The Lord Protector of England, Oliver Cromwell’s, 1655 Western Design. Harry was about 20-years-old at the time.

Dudley Pope, in Harry Morgan’s Way, was the first biographer I have seen pick up on Morgan’s nickname. I believe we can be sure Sir Henry was commonly known as Sir Harry, for that is traditionally the diminutive or nickname of men named Henry, which was common practice in his day. Harry is also the name used in the log-book of the ship Assistance when noting Morgan’s death.^[1] Besides, there is the slogan, “That is Harry Morgan’s way,” which became known throughout the West Indies.^[2]

^[1] National Archives of the UK (PRO): “August, 1688, Saturday 25th. This day about eleven hours morn’g, Sir Harry Morgan died. On the 26th was brought over from Passage Fort to the King’s House at Port Royall, from thence to the church, and after a sermon, was carried to the Pallisadoes and there buried. All the forts fired an equal number of guns. Wee fired two and twenty, and after wee and the Drake had fired, all the merchantmen fired.”

^[2] Cruikshank, The Life of Sir Henry Morgan, p. 121

Cromwell’s “Western Design” was for land and naval forces to be sent out from England to secure a base in the Caribbean to threaten Spain’s monopoly on trade routes throughout the hemisphere. If accomplished, this would weaken England’s main enemy of the day and lessen Roman Catholic influence in the New World.

William Penn

As a puritan, Cromwell had no love for Catholics. Such a scheme would have been popular in England at that time because many English people saw Spain as a cruel and unbending national enemy. Cromwell spoke of this in his speech to Parliament on 17 Sep 1656. “Abroad, our great enemy is the Spaniard,” he said. To Cromwell, conflict with Spain was a just and holy war.

Cromwell also believed he could wage war on Spain in the West Indies by taking advantage of the old doctrine of “no peace south of the line” without making a formal declaration of such in Europe.

The naval force came under the command of General-at-Sea, Vice-Admiral William Penn. General Robert Venables commanded the land force. While both were experienced and competent officers, neither was given the expedition’s overall command, which would prove unwise. Penn and Venables were given to believe the Spanish colony of Hispaniola (modern-day Haiti and the Dominican Republic) was weakly defended and could be taken easily, so it became the target.

Here is an excerpt from William Laird Clowes’s The Royal Navy, A History, From the Earliest Times to the Present Vol II of 1898:

Penn’s commission was dated October 9th. After enumerating Spanish outrages in America, assaults on planters, and the like, it went on to suggest that the King of Spain’s object then was “the ruin and destruction of all the English plantations, people, and interest in those parts.” Penn and Venables were therefore appointed for the express purpose of attacking that monarch [of Spain] in the West Indies. Besides dealing with his shipping, they were authorized to land men upon any of the dominions and possessions of the King of Spain in America.

Gen. Robert Venables

Under their joint command, and apparently, without a hard and fast plan, eighteen warships and twenty transport vessels set sail from Spithead on 25 Dec 1654. Penn's flagship was the 2nd rate warship Swiftsure.

A month later, the fleet reached the Caribbean island, Barbados, where Venables intended to add more recruits. The target size of his land forces was 8,000 men, but he had been unable to recruit that number in England.

While at Barbados, they found the Dutch were trading illegally with that colony and seized eight Dutch ships. Penn also ordered the formation of a 1,200-man regiment to be used onshore as a naval brigade. He appointed Vice-Admiral William Goodson of the 2nd rate Paragon as its onshore colonel and Benjamin Blake of the 3rd rate Gloucester as lieutenant-colonel. About 3,000 volunteers from among the island’s indentured servants and freemen enrolled at Barbados. War with Spain was always popular and usually profitable. The fleet sailed from Barbados on 31 Mar 1655, making stops to recruit a smaller number—about 1,300 in all—from the colonies on the islands of Antigua, Montserrat, Nevis, and St. Kitts.

Though their numbers were impressive on paper, Venables’ men were largely untrained and lacked military discipline. Many were more familiar with a prison cell than with an army barracks. Furthermore, supplies were already running low, and friction was developing between the joint commanders, Penn and Venables. Later, one of Venables’ officers would write:

We now find by sad experience that but few of them were old Soldiers, but certainly most of them were Apprentices that ran from their Masters, and others that came out of Bridewell, or one Gaol or another, so that in our poor Army we have but few that either fear God or reverence man.

Morale among the infantrymen suffered further when their commanders proclaimed that the Spanish settlements would not be plundered, depriving the men of much-anticipated booty. The English authorities wished to capture the colony intact to speed up later English colonization.

Continued …