The World’s Most Successful Pirate: 20 Facts About the Famous Bartholomew Roberts

Born in 1682 in the small village of Casnewydd Bach, between Fishguard and Haverfordwest in Pembrokeshire, Wales, John Roberts came into the world in a region steeped in maritime tradition. His father was most likely George Roberts, a local landowner. 

By 1719, Roberts had risen through the ranks to become second captain aboard the Princess, a slave ship operated by the Royal Africa Company. In June of that year, while anchored at Anomabu, the Princess was captured by the Welsh pirate Howell Davis. Roberts was forced to join the pirates.

When Captain Davis was killed in a Portuguese ambush on Príncipe Island in June 1719, the crew immediately needed a new leader. Although he had spent only six weeks on board, Roberts was unanimously elected captain because of his exceptional navigational skills and his frank and confident demeanor. 

Roberts’s first act as captain was swift revenge: he returned to Príncipe that very evening and destroyed the Portuguese fort, killing a large portion of the male population. The crew then sailed to Brazil and discovered a fleet of 42 Portuguese ships carrying treasure.

Hoisting Portuguese flags to blend in with the crowd, the man captured a smaller ship and forced its officer to identify the richest vessel, the Sagrada Familia, armed with 40 cannons and manned by a crew of 170. His pirates boarded the ship and captured it without firing a single shot.

After Walter Kennedy, a member of his crew, betrayed Roberts by stealing the Royal Rover and all its treasure while Roberts was pursuing another ship, the furious captain drew up official rules to prevent future mutinies. His pirate code was remarkably progressive for its time.

Roberts’ articles included revolutionary provisions regarding compensation that made his crew one of the best-protected at sea. Any pirate who lost a limb or became disabled while on duty received 800 Spanish dollars from the common fund, with proportional payments for less serious injuries. 

Unlike the scruffy appearance typically associated with pirates, Roberts cultivated a flamboyant and theatrical image. He wore a crimson damask waistcoat and breeches, a large tricorn hat adorned with a red feather, gold chains around his neck, and the diamond cross stolen from Portugal.

Contrary to the stereotype of rum-soaked pirate captains, this man was known to be teetotal, preferring tea to alcohol. He held religious services aboard his ships and is said never to have attacked on the Sabbath, although these pious habits stood in stark contrast to his brutality toward his enemies. 

Throughout his career, Roberts designed several provocative Jolly Roger flags, each telling a story of defiance and intimidation. His most famous work depicted him standing, sword in hand, atop two skulls bearing the inscriptions “ABH” (A Barbadian’s Head) and “AMH” (A Martinican’s Head).

He also commanded one of the most powerful pirate ships ever seen in Caribbean waters, repeatedly naming his flagship “Royal Fortune.” The most famous version was a French warship built in Bayonne around 1697, captured near Martinique, and manned by a crew of 200.

On June 21, 1720, Roberts sailed into Trepassey Harbor, Newfoundland, flying black flags and accompanied by the sound of drums and trumpets, in a theatrical display of intimidation. The harbor was home to 22 merchant ships and 150 fishing boats, all abandoned by their terrified captains.

Roberts’s most brazen act of revenge occurred when he captured the governor of Martinique, Florimond Hurault de Montigny. Posing as a friendly French merchant ship seeking information about pirates, Roberts fired a devastating volley at point-blank range as the ships drew near. 

Despite his past as an officer on a slave ship, Roberts showed cruel indifference toward slaves during his career as a pirate. In January 1722, in the port of Whydah, he captured eleven slave ships and demanded eight pounds of gold dust as ransom for the return of each ship. 

The pirate’s confidence was shattered when his Irish quartermaster, Walter Kennedy, committed the ultimate act of betrayal. While Roberts was leading 40 men in a small sloop to pursue a brigantine off the coast of Suriname, Kennedy fled with the Royal Rover.

In early February 1722, Roberts anchored his fleet at Cape Lopez, in what is now Gabon, to careen, clean, and repair the ships’ hulls. Captain Chaloner Ogle of the HMS Swallow spotted the pirate ships on February 5 and devised a clever ruse: he hoisted Portuguese flags and feigned retreat. 

As the HMS Swallow approached, the pirate put on his finest crimson damask waistcoat, his red-feathered hat, and his diamond cross, just as he always did before a battle. As the ships exchanged salvos during a tropical storm, a piece of grapeshot no bigger than a coin struck Roberts in the throat.

This man had made his crew promise that if he died in battle, they would immediately throw his body overboard to prevent the British authorities from displaying his chained corpse as a public warning. His loyal crew honored this wish by quickly weighting down his body.

The surviving crew members faced the largest mass trial of pirates in history at Cape Coast Castle in Ghana. Of the 272 pirates captured, 54 were sentenced to death: 52 were publicly hanged on the castle ramparts, while two were granted a last-minute reprieve. 

Roberts’s death on February 10, 1722, marked the definitive end of the golden age of piracy, as historians unanimously acknowledge. Captain Chaloner Ogle was knighted in 1723—the only British naval officer to have been honored specifically for his anti-piracy operations—and was subsequently promoted to admiral of the fleet.