Bartholomew "Black Bart" Roberts (1682-1722) was the most successful pirate of the "Golden Age of Piracy." Black Bart and his crew captured over 400 ships, more than the pirates Blackbeard, Edward Low, Jack Rackham and Francis Spriggs put together. At the height of his power, he had a fleet of four ships and hundreds of pirates, and gained 35 million U.S. dollars in loot. In his career he raided ships and ports from the Caribbean to Canada, and from Europe down to Africa. Black Bart had a reputation with his men for bravery and intelligence, and was viewed by some of his crew as being "pistol proof" in battle.
Roberts’ biggest plunder in a single haul was in a bay in Brazil. He came upon a Portuguese treasure fleet anchored off of Brazil. Pretending to be part of the convoy, he entered the bay and silently took one of the ships. From the captain of that ship, he found out which of the other ships had the most treasure. He then sailed up to that ship, attacked and boarded it before anyone knew what was happening. By the time the two massive Portuguese Men of War caught on to what was happening, Roberts was sailing away in his own ship, and the treasure ship he had just taken.
This is Black Bart's second flag,. It shows him standing upon 2 skulls, one labelled ABH (A Barbadian's Head) and the other AMH (A Martiniquian's Head). He had it made at a time when ships from Barbados and Martinique were out hunting pirates, after he had fought with two of these ships.