Diego Velázquez was born in Cuéllar, in the Segovia region of Spain. He fought in Naples before moving to Seville, where he met Bartolomeo Columbus. He first visited the New World with the crew of Christopher Columbus's second voyage in 1493. He settled in Hispaniola, which he helped pacify under the leadership of Governor Nicolás de Ovando. He then was active in leading the conquest of Cuba in 1511 under orders from Diego Columbus, recently restored as Viceroy of the Indies. He founded a number of new Spanish settlements and cities on the island, first Baracoa in 1512 and then most notably Santiago de Cuba in 1514 and Havana in 1515.
Velázquez was appointed governor of Cuba. The new settlers did not wish to be under the personal authority of Diego Columbus, so Velázquez convoked a general cabildo (a local government council) which was duly authorized to deal directly with Spain, and therefore removed Velázquez and the settlers from under the authority of Columbus, their nominal superior. It was a precedent that would come back to haunt him with the Mexican adventures. Noting the weakness of the Indians Velázquez authorized the importation of black slaves in 1513. He authorized various expeditions to explore lands further west, including the 1517 Francisco Hernández de Córdoba expedition to Yucatán (see: Spanish Conquest of Yucatán). In 1518 he was made the 1st Adelantado (Governor-General) of Cuba with jurisdiction over the former Governship of the Indies. He initially backed Hernán Cortés's famous expedition to Mexico, but when Cortés tried to seize and claim Mexico for himself, using the same cabildo technique. Velázquez charged Cortés with exceeding his authority and ordered Pánfilo de Narváez to arrest him. Cortés defeated Narvaez's troops in a surprise attack and persuaded the survivors to join him. Thus Velázquez saw none of the riches which came from Mexico. A further attempt to obtain redress in Spain resulted in a bitter loss to the Cortés faction. Diego Velázquez de Cuéllar died in Santiago de Cuba in 1524. After the conquest of Mexico, Cuba experienced an exodus of settlers. A decade later, Cuba was subjected to a new Viceroyalty of New Spain, after a political reorganization of the Indies.