Wanderlust World Wanderlust World Oliver Cromwell did not discover Jamaica. The island was first encountered by Christopher Columbus in 1494 and later colonized by the Spanish, who established Santiago de la Vega (now Spanish Town). In 1655, during Cromwell’s tenure as Lord Protector, an English expedition led by Admiral William Penn and General Robert Venables captured the island from Spain. Cromwell’s government then oversaw the establishment of English colonial administration.
Thus, Cromwell’s connection to Jamaica is through the Western Design military campaign that seized the island, not through discovery.