Bartholomew must have looked the very part of a pirate when dressed for action. A tall, dark man, he used to wear a rich damask waistcoat and breeches, a red feather in his cap, a gold chain round his neck with a large diamond cross dangling from it, a sword in his hand, and two pairs of pistols hanging at the end of a silk sling flung over his shoulders.
We first hear of Roberts as sailing, in honest employ, as master of the Princess (Captain Plumb), from London in November, 1719, bound for the coast of Guinea to pick up a cargo of "black ivory" at Anamaboe. Here his ship was taken by the Welsh pirate Howel Davis. At first Roberts was disinclined for the pirate life, but soon changed his mind.
On the death of Davis there were several candidates for the post of commander, all brisk and lively men, distinguished by the title of "Lords," such as Sympson, Ashplant, Anstis, and others. One of these "Lords," Dennis, concluded an eloquent harangue over a bowl of punch with a strong appeal for Roberts to be the new chief. This proposal was acclaimed with but one dissenting voice, that of "Lord" Sympson, who had hopes of being elected himself, and who sullenly left the meeting swearing "he did not care who they chose captain so it was not a papist." So Roberts was elected after being a pirate only six weeks; thus was true merit quickly appreciated and rewarded amongst them.
Roberts's speech to his fellow-pirates was short but to the point, saying "that since he had dipped his hands in muddy water, and must be a pyrate, it was better being a commander than a common man," not perhaps a graceful nor grateful way of expressing his thanks, but one which was no doubt understood by his audience.
Roberts began his career in a bright manner, for to revenge the perfectly justifiable death of their late captain he seized and razed the fort, bombarded the town, and setting on fire two Portuguese ships so as to act as torches, sailed away the same night. Sailing to Brazil they found in the Bay of Bahia a fleet of forty-two Portuguese ships ready laden and on the point of leaving for Lisbon, and Roberts, with the most astounding boldness, sailed right in amongst them until he found the deepest laden, which he attacked and boarded, although his was a much smaller ship. He sailed away with his prize from the harbour. This prize, amongst the merchandise, contained 40,000 moidors and a cross of diamonds designed for the King of Portugal.
He then took a Dutch ship, and two days later an English one, and sailed back to Brazil, refitting and cleaning at the Island of Ferdinando.
In a work such as this is, it is impossible to recount all, or even a few, of the daring adventures, or the piratical ups and downs of one pirate. Roberts sailed to the West Indies devastating the commerce of Jamaica and Barbadoes. When things grew too hot there, he went north to Newfoundland, and played the very devil with the English and French fishing fleets and settlements.