In 1682 a very religious George Roberts was welcomed with a son he named John in Haverfordwest, Wales who would one day become one of the most prominent pirates of the era. A few short years later at the disdain of his father began the journey at sea that would shape his life to come and at the age of thirteen joined the Royal Navy in 1695. This first voyage transpired into the next placement when he joined a ship used to transport slaves called the Princess in 1718. This led to an altercation with a pirate ship under the command of Howell Davis a year later and he was destined to be sold as a slave. The choice was to become a slave or join the crew as a pirate himself which he chose the latter and this led to being elected captain himself when Davis was killed in revenge, Roberts destroyed the town that caused his death. It is not known when or why he chose to change his name to Bartholomew Roberts but it was not uncommon for pirates to use an alias to protect their real identity.

Starting in the latter part of 1720, he began a reign of terror in the area of the West Indies which led to the seizure of at least a hundred ships. This act of piracy infuriated the provincial governors of the region and further flame the fires of hate when he hung one by a noose after capturing his ship. He also had the name "Black Bart" of which some accounts it was because of his hair and others from the cruelty of his deeds. It was during a sea battle with another ship the HMS Swallow that he was mortally wounded and as per his wishes the crew rendered his body to the deep. Roberts felt animosity for the occupants of Martinique and Barbados, which transferred to the flag flown on his ship of a man brandishing a flaming sword and dagger standing atop a pair of skulls. Under each skull had initials that portray his feeling of hatred for these people and translated to A.M.H., for A Marinican's Head, and A.B.H., for A Barbadian Head.