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He left for his second voyage ( 1493- 1496) on September 24 1493, with 17 ships carrying supplies and about 1200 men to assist in the subjugation of the Taíno and the colonization of the region.
He laid his course more southerly than on his first voyage, first sighting Dominica, which is quite rugged, so he turned north, discovering and naming Guadeloupe, Montserrat, Antigua, and Nevis in the Lesser Antilles, landing on them and claiming them for Spain as he did the Virgin Islands and Puerto Rico. He then went to Hispaniola, where he found his colonists had fallen into dispute with Indians in the interior and had been killed. He established a new settlement at Isabella, on the north coast of Hispaniola where gold had first been discovered; it was a poor location and the settlement was short-lived. He spent some time exploring the interior of the island for gold and did find some, establishing a small fort in the interior. He explored the south coast of Cuba but did not round the western end, thus convincing himself that it was a peninsula rather than an island, and discovered Jamaica.
Before he left on his second voyage he had been directed by Ferdinand and Isabella to maintain friendly, even loving relations with the natives. However, during his second voyage he sent a letter to the monarchs proposing to enslave some of the native peoples, specifically the Caribs, on the grounds of their aggressiveness. Although his petition was refused by the Crown, in February, 1495 Columbus took 1600 Arawak as slaves. 550 slaves were shipped back to Spain; two hundred died en route, probably of disease, and of the remainder half were ill when they arrived. After legal proceedings, the survivors were released and ordered to be shipped back home. Some of the 1600 were kept as slaves for Columbus's men, Columbus recorded using slaves for sex in his journal. The remaining 400, who Columbus had no use for, were let go and fled into the hills, making, according to Columbus, prospects for their future capture dim. Rounding up the slaves resulted in the first major battle between the Spanish and the Indians in the new world.
The main objective of Columbus's journey had been gold. To further this goal, he imposed a system on the natives in Cicao on Haiti, whereby all those above fourteen years of age had to find a certain quota of gold, which would be signified by a token placed around their necks. Those who failed to reach their quota would have their hands chopped off. Despite such extreme measures, Columbus did not manage to obtain much gold. One of the primary reasons for this was the native susceptibility to European diseases.
In his letters to the Spanish king and queen, Columbus would repeatedly suggest slavery as a way to profit from the new discoveries, but these suggestions were all rejected: the monarchs preferred to view the natives as future members of Christendom.
More importantly, Columbus oversaw the establishment of the encomienda (trusteeship) system, by which Spaniards were granted exclusive use of Indian labor in return for converting them to Christianity; this policy amounted to enslavement of the local population. In some cases, Indians were worked to death; in other cases they died due to newly introduced diseases and malnutrition. Estimates of the pre-Columbian population vary enormously; see fuller discussion at Taíno. Cook and Borah (see references below) estimated the native population (Taíno) of Hispanola at the time of Columbus's conquest in 1493 at 8,000,000, probably the highest estimate. In 1496 Bartolome de las Casas conducted a census after the conquest and initial imposition of the encomienda system, arriving at an estimate of only 3,000,000 Taíno. A Spanish census in 1514 records only 22,000 Taíno, and a census in 1542 recorded only 200. Columbus established his brothers as commanders of the settlements and left Hispaniola for Europe on March 10, 1496; they and other Spanish conquerors employed the encomienda system with similar results elsewhere in the Americas.
In 1498, Columbus left for the New World a third time, accompanied by the young Bartolome de Las Casas, who would later provide partial transcripts of Columbus's logs. This time he discovered the island of Trinidad ( July 31) and the mainland of South America, including the Orinoco River, before returning to Hispaniola. Initially, he described the new lands as belonging to a previously unknown new continent, but later he retreated to his position that they belonged to Asia.
Many of the Spanish settlers of the new colony were discontent, having been misled by Columbus about the supposedly bountiful riches of the new world. Columbus repeatedly had to deal with rebellious settlers and Indians. He had some of his crew hanged for disobeying him. A number of returned settlers and friars lobbied against Columbus at the Spanish court, accusing him of mismanagement. The king and queen sent the royal administrator Francisco de Bobadilla in 1500, who upon arrival ( August 23) detained Columbus and his brothers and had them shipped home. Columbus refused to have his shackles removed on the trip to Spain, during which he wrote a long and pleading letter to the Spanish monarchs.
Although he regained his freedom, he did not regain his prestige and lost his governorship. As an added insult, the Portuguese had won the race to the Indies: Vasco da Gama returned in September 1499 from a trip to India, having sailed east around Africa.