How and Why the Pirates in Caribbean were successful
Pirates in the Mediterranean, called 'Corsairs' , operated with the permission of the potentates of the various states of North Africa. Their activities increased when Spain drove the Moors out. The Moors used Piracy as a guerrilla war. They were very powerful and successful.
This Piracy was one of the reasons why many Capitals in Europe were not on the Coast and that not traveling in the Mediterranean but overland preferred. This was why finding a pirate-less passage to India or China had Columbus going West to reach the East.
Hence Moorish Piracy had a very positive influence on European exploration.
The Spanish Empire 'owned' the lands that Columbus 'discovered'. This meant almost the entire New World belonged to Spain. The only other 'legal' owner was ally of Spain, Portugal.
The late 1400s into the 1500s was the time of a great religious upheaval in Europe.
Firstly, there was the Spanish Inquisition where Jews were killed or forced to convert to Catholicism.
Secondly there was dissatisfaction with the Church leading to Protestantism.
The Political aspect must be noted. The Pope was not only a religious but a political figure with a great deal of worldly power. This power was used for earthly gain.
Hence Spain being the home of fanatical Catholics and owning the New World as it were, was not in the interest of other European powers.
No Peace Beyond the Line
As no nation in Europe could afford to fight a war with Spain over its New World possessions. Spain was rich, powerful, and no nation one wished to offend.
The wisest idea was to allow non-governmental agencies to loot the Spanish treasure fleet. This kind of deception, in which 'private' persons who happen to have the nationality of a particular country could act in a manner the State can deny. Hence Pirate ships were not acting as the English or Dutch or French navy, they were 'criminals'.
Although under the agreement between the Crown and the pirate a percentage of the take was to be remitted to the particular Throne, this was a private contract, not to be discussed in public.
A number of Pirates had no such agreement, and did act on their own, but most were acting as secret agents for their particular King or Queen.
Besides the actual Pirates who boarded and looted the Spanish treasury ships there where those who gave information to the Pirates/Privateers for which the received some financial reward, although the real impetus was the weakening of the hated Spanish.
Passing the Secret Information
Aruba and Curacao sit at the mouth of the Maricabo. It was from this river that Spanish Ships would be loaded with silver taken from deep within the Andes. The ships would pass through the straits and often stop at Aruba or Curacao to take on water or supplies.
These islands were occupied by the Dutch. A large number of the Dutch were Jews. These were people who had been driven out of Spain and taken refuge in Holland. They had been encouraged to immigrate to the New World.
Some Jews went to Northern Brasil, some to Suriname, and others took residence in Curacao and Aruba.
In this time, being a 'merchant' was a sneered upon profession. Most Jews were merchants. As Jews might not be allowed to own land, they would go into business.
These Dutch Jews had the benefit of understanding Spanish.
As the Spanish were unaware that the shopkeeper in this store in Aruba had once lived in Spain before the Inquisition, they saw no reason to guard their tongues. The Jewish merchants heard everything, knew everything, and would send messages to those in Port Royal (Jamaica) or one of the other islands, so that the Pirates/Privateers knew exactly how many ships, how many men, how many cannon, how much silver was on board along with the most important fact; the route.
Pirate attacks were not haphazard, they were carefully planned down to the last detail. For a Spanish fleet, no matter how well guarded, to get out of the Caribbean became less and less likely as time went on.
Becoming Rich making Spain poor
Spain could not protect its vast Empire. Various islands were soon settled and captured by other nations, primarily England. Jamaica, which was not particularly important to the Spanish was taken in 1655 by the English who realising they could not defend it, invited pirates to use Port Royal as their base.
Tortuga, an island just off the Coast of Haiti was another popular Pirate port as
was Gonave, off Haiti. A little island called Padre, off the coast of Texas was a
base as was New Providence in the Bahamas.
The Pirates, forming a confederation called 'The Brethren of the Coast', vowed to fight to the last man standing against Spain. They shared the information, so just in case the Spanish made it past the Leeward and then Windward Islands, they'd be caught in the Atlantic by those from the Bahamas.
By the mid 1600s Spain no longer owned the world. Although it had enormous holdings in South and Central America, the British and French and Dutch owned many of the Islands and were strong and rich from the booty obtained by Pirates.
Using 'unofficial' groups, such as Pirates/Privateers, where the Nation to which these persons belonged could deny any complicity was how Spain was defeated. It was not a direct confrontation.
The Pirates/Privateers had a lot of support from their home countries, whether given the ships, the arms, or finances to operate. They had one of the greatest 'information highways'.
No ship left Venezuela which was not known, mapped, tracked, and the information widely disseminated.
While a Spanish ship was delayed in an Aruba port, small fast ships were racing to Jamaica with the data, including the time the 'delay' would end so that Pirate ships were not floating aimlessly waiting for what may or may not happen, but actually had enough information to do 'surgical' strikes.