Europe's interaction with the Caribbean began in 1492 with the Spanish sponsored voyages of Christopher Columbus. Columbus' voyages to the Caribbean incorporated two differing traditions of expansion. The first was influenced by his Genoese roots and his experience in the Portuguese mercantile system. This background allowed Columbus to view his task as mainly one of discovery to be followed by the establishment of commercial outposts and trading centres that would tap into indigenous resources. The primary goal of this system was the quick exploitation of the local area with minimum investment. This contrasted dramatically with the Spanish Castilian tradition born of the reconquista that emphasised a military advance, followed by the sharing out of new lands and booty. The primary goal of this system was the conquest and eventual settlement of new lands for the purpose of long term exploitation. The difference between these two traditions created expectations that brought Columbus into immediate conflict with the Spanish settlers who accompanied him. The Crown was called on in several occasions to mediate between Columbus and the settlers, usually deciding in their countrymen's favour. By his death in 1506 Columbus had already fallen to the wayside of Spanish exploration because he was a poor governor in the Spanish tradition.

This Spanish pattern of conquest and settlement became the standard for Spanish exploration in the New World. Upon discovering a new territory, the Spanish expeditions were usually, but not always, greeted by friendly inhabitants. During this initial stage the Europeans would survey the area and the people to determine their potential for exploitation. Within a short period of time the inhabitants would grow to resent the Spanish who helped themselves to 'the natives' food, women and gold.' Such abuses were common in Spanish cross-cultural contact and provoked violent reactions by various indigenous populations. On the island of Hispaniola a group of tribal leaders, joined forces to expel the Spaniards from the island. The Spaniards, who had the benefit of muskets, arquebuses, armour, and savage dogs ruthlessly put these uprisings down and took captive the tribal leaders to ensure native co-operation. Once native resistance was crushed the Spanish forced the villages to grow cash crops, pay tribute, and mine for their precious gold. The Spanish regime was brutal and violent. Rapes and massacres were casual and frequent in occurrence, rationalised by a racist worldview that justified the exploitation of non-Christians or non-whites.

The Spanish ventures in the Caribbean had to recoup their sponsors' initial investment and this led to an obsession with discovering gold deposits. Once these deposits were found the Spanish had to secure sufficient labour to mine it so the encomienda system was instituted by the Spanish Crown to regulate the new settlements. An encomienda was a grant of land with a number of indigenous slaves given to a settler, whose only obligation was to bring Christianity to his slaves. Unfortunately for these slaves the spread of European disease, a harsh labour regime, and brutal mistreatment decimated their population. The Spanish were forced to send out expeditions to neighbouring islands to capture slaves to replenish their exhausted labour supply.

The exhaustion of gold deposits and labour in the Caribbean led to the full-scale occupation and exploitation of Puerto Rico, Jamaica, and Cuba between 1508-1511. Each occupation followed the same pattern of discovery, local conquest, settlement, exhaustive exploitation, and finally a push into the frontier for new natural resources and slaves. The men who led these campaigns were known as the conquistadors. They adapted the reconquista pattern of military expedition and settlement, often exploiting the pre-existing indigenous rivalries in order to divide and conquer with extreme efficiency. The quest for gold brought the conquistadors to the mainland of Central America where they would repeat the conquest pattern that had been so effective in the Caribbean, to defeat the Aztec and Inca Empires.

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