Pirates > Flying Gang
The Flying Gang was the group of famous ex-privateers turned outlaw pirates during the Post Spanish Succession Period. They made their home at the pirate haven of Nassau on the unpopulated island of New Providence in the British controlled Bahamas. Most of the pirates had previously served in the privateer army out of Port Royal on the island of British Jamaica during the War of the Spanish Succession. However, upon the peace that was ushered in by the signing of the Treaty of Utrecht the thousands of privateers suddenly found themselves without unemployment.
They hit pay-dirt when the 1715 Spanish Treasure Fleet sunk off the coast of La Florida. The Spanish quickly built a salvage camp to attempt to rescue even a small percentage of the unimaginable wealth. However, the Flying Gang had other plans and raided the salvage camp and became extremely wealthy in the process. This heist is known as one of the greatest acts of piracy in the West Indies and allowed the pirates to not only build their own Republic of Pirates but become outright pirates in their own right.
The Flying Gang was really started by veteran privateers Henry Jennings who led the raid on the Spanish salvage camp along with Samuel Bellamy, Charles Vane, Benjamin Hornigold and many others. These pirates would take their wealth and Hornigold and fellow pirate Thomas Barrow established a new government on the island and set to work building a legitimate pirate republic.
The Flying Gang started the careers of men like Edward 'Blackbeard' Teach who was on Hornigold's crew before he assumed captaincy in his own right. It also started the careers of Edward England and eventually grew to include many other pirates including Olivier Levasseur and many others. The Flying Gang was one of the most influential groups of pirates alongside the Brethren of the Coast and one of the most powerful in the entire Golden Age of Piracy. In fact at one point the British were legitimately worried about the pirates establishing their own breakaway civilization in the West Indies that would threaten the colonial power structure.
Therefore the group of ex-privateers soon became an enemy to all of their previous employers and therefore had to be stamped out. While they were once considered allies, now they were considered outlaws and with no other job prospects save work in the torturous Royal Navy or the even worse merchant ships the pirates simply chose to expand their market and include flags of all nations.
Overall the Flying Gang were the most successful of the pirates in terms of wealth gained and can only be compared with Henry Every. While they are famous for pirating the West Indies the Flying Gang also terrorized the coast of North America and a few of them even attempted a second Pirate Round.