Imperial Designs: Cromwell’s Conquest of Jamaica
The Lord Protector’s move on Jamaica transformed Britain’s early empire.

A massive fleet set sail for Hispaniola in 1654 to conquer the Spanish Caribbean island for the Lord Protector, Oliver Cromwell. Repulsed after three weeks by a much smaller and poorly armed force, the fleet limped away to Jamaica. Botching that conquest as well, the army hunkered down for what would prove a long guerilla war against a small but tenacious remnant of the island’s population. The fleet’s commanders scurried home, where Cromwell threw them in the Tower for abandoning their posts. It was not the Protector’s finest hour.