In 1495, after 3 years of continuous brutalization, enslavement and deaths of the Taino/Arawaks by the Spaniards;  Caonabo join forces with his wife Anacaona and the Cacique of Magua who was also his brother; Guarionex, in order to chase the Spaniards off the Island.Together they rallied over 3.000 men armed with their bows and arrows, spears and other primitive defensematerials; organized a battle to fight off the Spaniards.


The Spanish army, although over matched by the Natives' in numbers,  were heavily armored with some of the world's most powerful weapons at the time, such as guns and canons, easily won the battle. The man-eating dogs, and horses they brought along, made the defeat of the Natives even easier.
Caonabo and his wife Anacaona were among the marginal who survived the bloody battle; his brother Guarionex didn't make it. They escaped, but vowed to continue the fight for the freedom of their people till their deaths.

Almost immediately after loosing the Vega Real Battle, Caonabo and his wife Anacaona were already looking for more men to fight another one, they weren't about to give up.
 Both Christopher Columbus and, Ojeda de Ovando who was the leader of the small Spanish army, feared that the Taino/Arawaks would never give up their fights for freedom as long as  Caonabo and Anacaona were around. Ojeda de Ovando invited the King and Queen  to a so called "peace meeting"; he asked them to come alone, only the leaders were necessary at such a meeting he said, but as soon as Caonabo and Queen Anacaona arrived, the men of Ojeda de Ovando, captured them. Caonabo was put on ship en route to Spain, as for Queen Anacaona, she was hanged.