A flag commonly attributed to Bartholomew Roberts depicts him holding a glass out to toast a skeleton holding a spear, which represents death. It originates from volume 29 of the journal Mariner’s Mirror in 1943. The same flag with an hourglass instead of drinking glass first appeared in the historian Basil Lubbock’s 1922 book The Blackwall Frigates, inspired by an illustration from 2nd edition of A General History from 1724.
This flag depicts Bartholomew Roberts holding a sword while standing on two skulls: under one is written ABH, under the other AMH, standing for a Barbadian’s Head and A Martinican’s head respectively. Later he is depicted as holding a flaming sword. It is said to portray Robert’s animosity towards those two islands after their governors attempted to capture him. The only evidence for this flag is A General History of the Pyrates, depicted with the cross of St. George in top right corner in the first edition. ‘… a Man pourtrayed [sic] in it, with a flaming Sword in his hand, and standing on two Skulls, subscribed A.B.H. And A.M.H.’
One of two flags reported to have been flown by Black Sam Bellamy, known as the Robin hood of pirates, according to an eyewitness account in the Weekly Journal of London. It was possibly flown during Bellamy’s time in command of the Whydah Gally. “… when they began any Attack they spread a back Ensign, with Death holding an Hour-Glass in one hand and a trumpet in the other.” Weekly Journal, July 1717
One of two flags reported to have been flown by Black Sam Bellamy, known as the Robin hood of pirates, by Thomas Blanket, one of the eight pirates on trial after the wreck of the Whydah in a storm. It was a flag that seems to have been common to members of the Flying Gang of Nassau and was possibly flown before Bellamy captured the Whydah. “They spread a large black Flag, with a death‘s Head and Bones a-cross.” The Trials of Eight Persons Indicted for Piracy, Boston 1718. According to the article The Pirate Ship Whydah: Pirate strategy on the Field Museum in Chicago’s website, this flag is also mentioned by Thomas Baker, one of Bellamy’s crew, although no sources is given: “…they spread a large black flag, with a Death’s Head and Bones across, and gave chase to Cap’t. Prince under the same colours.”
This flag is believed to have been flown by Ned Lowe and his consorts, Charles Harris of the 8-gun sloop the Ranger and Francis Spriggs, Lowe’s ex-quartermaster, of the schooner the Delight. Charles Harris was captured by Peter Solgard of HMS Greyhound in June 1723. Spriggs fate is uncertain, but some believe he was marooned together with Ned Lowe. “Black Ensign with a white Skeleton in the middle of it, with a Dart in One Hand striking a bleeding Heart, and in the other an Hourglass.” – Captain Johnson, A General History of the Pyrates.