[2] Scholars believe that the Spanish term cimarron comes from the Taino word si'maran meaning “wild, savage, gone astray”.
Viceroy Canete felt unable to subdue these maroons, so he offered them terms that entailed a recognition of their freedom, provided they refused to admit any newcomers and returned runaways to their owners.
John Hawkins of Plymouth, England became one of Queen Elizabeth's first "sea dogs" and became involved in the African slave trade in Spanish America.
While waiting for the treasure to arrive, he made contact with the Cimarrons (whose population was around 3,000),[7] whom he described as “certaine valiant Negros fled from their cruel masters the Spaniards”.
The first Cimarron he encountered was named Pedro Mandiga (or Mandinga), who helped guide Drake and his men across the Chagres River to Spanish outposts.
In February 1573, the Cimarrons informed Drake that the Spanish mule trains carrying the gold (also known as the flota) were sighted in Nombre de Dios and were moving across the Isthmus.
Drake, guided by 30 Cimarrones through a series of hidden pathways and accompanied by John Oxenham, embarked on a journey to intercept the gold.
Once they arrived at the spot where they planned to carry out their ambush in Nombre de Dios, a Cimarron spy was sent to the Spanish post to find out when the treasure procession would begin.
The Cimarrons cared little about getting a part of the stolen gold or silver, but rather desired iron, which Drake handed over to them in plentiful amounts.
During this raid, the raiders collected all the gold, silver and jewels they could, liberated seventy slaves, who were turned over to the Cimarrons, and desecrated the churches.
The Spanish feared the Cimarron alliance with the English, believing it might lead to larger scale expeditions and possibly even settlement.
Citizens of Panama wrote anxious letters to Madrid complaining about how the cimarrons were inflicting heavy damage in robbery, plunder and death.
In 1577, the Spanish sent a well armed body of volunteers from Panama to invade the Cimarron settlements and burn all of their crops and villages.
By 1579, when this had been accomplished, the Cimarrons agreed to settle in a large pueblo where they enjoyed some measure of self-determination under Spanish rule.
[citation needed] The news of Sir Francis Drake's adventures and alliances with the Cimarrons was reaching England and the Western world.
Drake's travels inspired another "sea dog", Richard Hakluyt, to propose the establishment of English naval bases in Magellan's Strait and in southern Brazil to be manned by pirates, convicts and Cimarrones.
He believed that the Cimarrons were "a people detesting the proud governance of the Spaniards" and so would gladly move to these new colonies by the hundreds or thousands.