Alternative History
Colony of Jamaica
— Colony of the Commonwealth of England, Scotland and Ireland
Timeline: Cromwell the Great

OTL equivalent: Jamaica (1655–1962) and Cayman Islands
Flag Jamaica Coat of Arms Jamaica
Location Jamaica
Location of Jamaica
Indus Uterque Serviet Uni (Latin)
("The two Indies will serve as one")
Capital Cagway[1] (until 1692), Port Oliver[2] (since 1692)
Largest City Port Oliver
Other Cities Cagway and Spanish Town
  Others Spanish, Gaelic Irish, Jamaican Patois and Taíno
Church of England
  Others Other protestant denominations (mainly Independents, Baptists and Quakers and Presbyterians) Roman Catholics and Animism
Ethnic Groups
European (English, Scots, Welsh, Irish, and Spanish)
  Others Maroons and Tiano (also called Arawak)
Demonym Jamaican
Government Colony of Commonwealth of England
  Legislature House of Assembly
Lord Protector Charlotte Hastings-Rawle
Governor-Commissioner Sydney Hallowes
Population 2.700.000 
Established 1655 (from Spain)
Currency Pound sterling and Spanish dollar -> West Indies dollar
Time Zone UTC -5

For, behold, I create new heavens and a new earth: and the former shall not be remembered, nor come into mind.
(Isaiah 65:17, King James Bible)

The Colony of Jamaica is a Commonwealth colony in the Caribbean captured by the English from Spain in 1655 and formally ceded Jamaica to the British. Jamaica is a haven of privateers, buccaneers, and occasionally outright pirates. It also has several self-ruling communities of former slaves (maroons).

Capture of Jamaica

In late 1654, Cromwell launched the Western Design armada against Spain's colonies in the Caribbean. In April 1655, General Robert Venables led the armada in an attack on Spain's fort at Santo Domingo, Hispaniola. However, the Spanish repulsed this poorly-executed attack, known as the Siege of Santo Domingo, and the English troops were soon decimated by disease.

Weakened by fever and looking for an easy victory following their defeat at Santo Domingo, the English force then sailed for Jamaica, the only Spanish West Indies island that did not have new defensive works. In May 1655, around 7000 English soldiers landed near Jamaica's Spanish Town capital. The English invasion force soon overwhelmed the small number of Spanish troops (at the time, Jamaica's entire population only numbered around 2500).

In the following years, Spain repeatedly attempted to recapture Jamaica, and in response in 1657 Governor D'Oyley invited buccaneers to base themselves at Port Royal on Santiago, to help defend against Spanish attacks. Spain never recaptured Jamaica.

Settlement and colonization

Cromwell sought to fill Jamaica with the godly, the choice was to have families of New England colonize Jamaica. Promises of free transport, cheap land, immunity from taxation, and local self-government were the inducements. However, the island's white population was increased and colonized by sending indentured servants and prisoners captured in battles with the Irish and Scots, as well as common criminals. The white population was also augmented by immigrants from the North American mainland and other islands, as well as by the English buccaneers.

By 1661 the population of the island was only 3500 despite the fact that 12,000 had arrived in the previous five years more than hinting at the horrific mortality rat0 by diseases. Later African slaves were imported to work in the plantations becoming a large part of the population.

Governor D'Oyley had to clamp down pillage and desertion from the army. In August 1660 discontented army officials and troop mutinied against D'Oyley led by colonels Raymond and Tyson. Their demands were for land, payment of army arrears and end of military rule. However, differences were also political between D'Oyley's social conservatism and the radical republicanism of Raymond and Tyson. The mutiny failed and its leaders shot. But the ideas of radical republicanism were not forgotten by the survivors of the mutineers in years to come.

In 1662 arrived Sir Thomas Lynch replacing D'Oyley as governor. Under Lynch the basis of the civil administration of colony were established along an elected Assembly, division of the territory in parishes, a judiciary, and treasury and local militia. A land survey was ordered under that enabled the partition of land to colonists. As part of his commission he proclaimed an amnesty for deserting soldiers and payment of arrears. Along freedom of religion, as in the Commonwealth, the Church of England was established in the parishes.


Social hierarchy Jamaica, in contrast to the Commonwealth homeland, as little importance. This due that all colonizers were either prisoners, criminals, buccaneers and former soldiers of the Commonwealth and none could claim noble birth. Wealth, expressed in landowning or wealth of commerce and trade became the social differentiation

The republican radicalism of the revolt 1660 also contribute to the common perception of the liberty of men and their right to manage their affairs as expressed in spontaneous assemblies and establishment of local government in the late 1660s.

As part of the legacy of the mutineers of 1660 town hall meetings administered the local needs and petitioned the central government for improvements. Parish councils, as the union of town hall meetings were legally established in 1675.

As an incentive for colonization it was proclaimed in 1667 that the white population not under indentured labor or criminals were freeman and could claim or register for land tenure. The rights of freeman included civic rights and election to political office, meaning in practice that all the white population had participation in the government of Jamaica - becoming in time a cause of trouble and discord between Governors and the white population.


First proposed flag of Jamaica.svg
Flag of Jamaica.svg

Historical Marron flags

Black Militia Flag

When the British captured Jamaica in 1655, the Spanish colonists fled, leaving a large number of African slaves. These former Spanish slaves (maroons) created three Palenques, or settlements. Former slaves organized under the leadership of Juan de Serras allied with the Spanish guerrillas on the western end of the Cockpit Country, while those under Juan de Bolas established themselves and served as a "black militia" for the English. The third chose to join those who had previously escaped from the Spanish to live and intermarry with the Arawak people.

Each group of Maroons established distinct independent communities in the mountainous interior of Jamaica. They survived by subsistence farming and periodic raids of plantations. Over time, the Maroons came to control large areas of the Jamaican interior.

The extensive development of sugar cane plantations expanded the importation of slaves as labor force. Africans in Jamaica continually fought and revolted, with many who escaped becoming Maroon. The revolts had the effect of disrupting the sugar economy in Jamaica and making it less profitable.

The Haitian Revolution 1791-1798 had a huge impact as Maroon communities started to coordinate under common political leaderships and making more bold attacks and freeing slaves of the sugar plantations. Some incursions even siege coastal cities and also affecting Port Spain Kingston.

The revolts simmered down only after the British government promised to free the slaves if they stopped revolting; and slavery was abolished in 1811 in the whole island.


With the establishment of civil government in 1661, Jamaica was administered by an appointed governor acting with the advice of a nominated council in the legislature. The legislature consisted of the governor and an elected House of Assembly. The Charter of 1826 established self government with a Governor-Commissioner, appointed by the Lord Protector on advise of the House of Assembly and assisted by a Governance Commission named by the Governor-Commissioner. The new Charter changed the voting qualifications in a way that enabled a significant number of blacks and people of mixed race to vote, but placed property ownership restrictions on them, which excluded the majority of non-white men from voting for the House of Assembly but allowed a greater number of them to vote in the elections of parish councils.

Military Commander (1655-1662)
  • ...
  • Major-General Edward D'Oyley 1657–1662
Governor (1662-1827)
  • Sir Thomas Lynch 1662-1672
  • Sir Thomas Modyford 1672-1680
  • Sir Henry Morgan, 1680–...
  • ....
Governor-Commissioner (1827 to date)
  • ...
  • Sydney Hallowes

  1. OTL Port Royal
  2. OTL Kingston