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.

When Spain drove the Moors out, many used Piracy as guerrilla war.

Piracy was one of the reasons why not traveling in the Mediterranean but overland was preferred. And why finding a pirate-less passage to India or China had Columbus going West to reach the East.

Hence Piracy had a very positive influence on exploration.

The Spanish Empire took control over all the lands that Columbus 'discovered'. This meant almost the entire New World belonged to Spain.

At this time in history there was a religious upheaval going on.

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, for not only had the Pope been a religious but was a political figure with a great deal of worldly power, which 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.

As no nation in Europe could afford to fight a war with Spain over its New World possessions, the wisest idea was to allow non-governmental agencies to loot the Spanish treasure fleet.  The ships were not acting as the English or Dutch or French navy.

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.

Of course many of the Pirates had no such agreement, and did act on their own, but many were acting as secret agents for their particular King or Queen.

Others gave information to the Pirates/Privateers for which their reward was the weakening of the hated Spanish. 

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.  Many of the Dutch were Jews who had been driven out of Spain, taken refuge in Holland, and then been encourage to emigrate to the New World. Many arrived in Northern Brasil, in Suriname, and in Curacao and Aruba.

They would send messages to various persons in Port Royal or on one of the other islands, so that the Pirates/Privateers knew exactly how many ships, how many men, how many cannon and how much silver was on board.

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.

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.
A little island called Padre, off the coast of Texas was another such 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.

By the mid 1600s Spain did not own the world, although it had enormous holdings in South and Central America, the British and French and Dutch were strong and rich from the booty obtained by Pirates.