Even though he was only a pirate for three years, Bartholomew Roberts is perhaps the most successful pirate on this list. From 1719 to 1722, Roberts captured over 400 prizes.
Roberts began his career of piracy June of 1719. The ship he was on was captured by pirates under Howell Davis. The pirates forced Roberts and several of his men to join them. Then they set sail for the island of Principe off the west coast of Africa.
At Principe, Captain Davis was shot dead by the Portuguese garrison, who had found out that he and his crew were pirates. With Davis dead, a new captain had to be elected — Roberts.
Although he initially had not wanted to join the pirates, Roberts accepted his promotion to captain. He reasoned that if he was going to be a pirate, it was better to be captain than a common man.
After his election to captain, Roberts drew up his first flag, which showed him together with Death, holding an hourglass.