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Cuba (1511–1519)

In 1511, Cortés accompanied Diego Velázquez de Cuéllar, an aide of the Governor of Hispaniola, in his expedition to conquer Cuba. Velázquez was appointed Governor of New Spain. At the age of 26, Cortés was made clerk to the treasurer with the responsibility of ensuring that the Crown received the quinto, or customary one fifth of the profits from the expedition.

Velázquez was so impressed with Cortés that he secured a high political position for him in the colony. He became secretary for Governor Velázquez. Cortés was twice appointed municipal magistrate (alcalde) of Santiago. In Cuba, Cortés became a man of substance with an encomienda to provide Indian labor for his mines and cattle. This new position of power also made him the new source of leadership, which opposing forces in the colony could then turn to. In 1514, Cortés led a group which demanded that more Indians be assigned to the settlers.

As time went on, relations between Cortés and Governor Velázquez became strained. Cortés found time to become romantically involved with Catalina Xuárez (or Juárez), the sister-in-law of Governor Velázquez. Part of Velázquez's displeasure seems to have been based on a belief that Cortés was trifling with Catalina's affections. Cortés was temporarily distracted by one of Catalina's sisters but finally married Catalina, reluctantly, under pressure from Governor Velázquez. However, by doing so, he hoped to secure the good will of both her family and that of Velázquez.

It was not until he had been almost 15 years in the Indies that Cortés began to look beyond his substantial status as mayor of the capital of Cuba and as a man of affairs in the thriving colony. He missed the first two expeditions, under the orders of Francisco Hernández de Córdoba and then Juan de Grijalva, sent by Diego Velázquez to Mexico in 1518. News reached Velázquez that Juan de Grijalva had established a colony on the mainland where there was a bonanza of silver and gold, and Velázquez decided to send him help. Cortés was appointed captain-general of this new expedition in October 1518, but was advised to move fast before Velázquez changed his mind.

With Cortés's experience as an administrator, knowledge gained from many failed expeditions, and his impeccable rhetoric he was able to gather six ships and 300 men, within a month. Velázquez's jealousy exploded and he decided to put the expedition in other hands. However, Cortés quickly gathered more men and ships in other Cuban ports.