Founded in 1493 by Christopher Columbus and some 1500 Spanish settlers under his command, La Isabela was strategically located on a defensible ocean bluff but far from fresh water and fertile soil, oversights that led to its abandonment in favour of Santo Domingo after only four years. Columbus intended that it would become the gold-bearing capital of Spain’s empire, organizing it according to the factoria system of Portugal’s colonies along the northwest coast of Africa; in these, a small group of entrepreneurial partners forced natives to hand over a valuable local commodity (in this case, gold), either as tribute or in exchange for European goods at a ridiculously low rate.

However, it soon became evident that there was not much gold to be had, and after yellow fever and malaria killed half of the original settlers, the rest became increasingly disgusted. Another sticking point was the tradition of Christian conquest in Spain, which allowed soldiers to enslave Moors on conquered lands. At first Columbus opposed transplanting slavery here, and as hardships mounted he demanded that colonists perform manual labour regardless of rank, alienating the petty nobility. After a failed coup attempt, several nobles stole one of his boats and set off for Spain to complain of the goings-on. In mid-1494, Columbus, perhaps realizing that he was in danger of losing the faith of his men, waged two military campaigns to capture Tainos, allotting slaves to his men in lieu of monthly wages. The Indians were to work the surrounding fields, though many were able to escape.

Two years later Columbus sailed to Spain to request more settlers, leaving his brother Bartolomé in charge of La Isabela. On his departure, a group of colonists led by Columbus’s personal servant Francisco Roldán revolted and went to settle in the outlying countryside. Bartolomé abandoned La Isabela in 1497 with his few remaining men for the site of Santo Domingo, where one Spaniard had found a large gold nugget. On Columbus’s return in 1498, his town lay abandoned; two years later, he was removed from command in Santo Domingo and sent back to Spain in disgrace.

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