An expedition sent out by Oliver Cromwell under Admiral William Penn (the father of the founder of Pennsylvania) and General Robert Venables in 1655 seize Jamaica, the first territory captured from the Spanish. (Trinidad, the only other British colony taken from the Spanish, will fall in 1797 and will be ceded in 1802.)

Jamaica at this time as a population of about three thousand, equally divided between Spaniards and their slaves—the native population having been eliminated.

Although Jamaica is a disappointing consolation for the failure to capture either of the major colonies of Hispaniola or Cuba, the island is retained in the Treaty of Madrid in 1670, thereby more than doubling the land area for potential English colonization in the Caribbean.

Jamaica will be the most important of Britain's Caribbean colonies by 1750, having eclipsed Barbados in economic significance.