Bartholomew Roberts- active 1719–1722
This is the first flag of famed pirate Bartholomew Roberts, AKA, Black Bart. The flag depicted him and death holding an hourglass. Simple, darkly beautiful, and down right menacing.
Bartholomew Roberts- active 1719–1722
We’re still hanging out with Black Bart here, as he’s actually had TWO flags during his career as a swashbuckling lunatic. This one features him standing on top of two skulls representing the heads of a Barbadian and a Martiniquian. Apparently, the “ABH and AMH” are just ways to describe the skulls as being Barbadian and Martiniquian ones.
“Black Sam” Bellamy- active 1716 – April 26, 1717
Sam Bellamy, although only a pirate for a short time, is responsible for the most famous pirate flag around- the skull and cross bones. You didn’t want to see this thing start to make its way up the pole if you were on another ship, that is for damn sure.
Edward Teach- active 1716–1718
Otherwise known as “Black Beard” this man had a real eye for showmanship, especially when it came to fighting. However, before the fight, came the flag, and his was pretty sick. His flag consisted of a black flag with a horned skeleton, an hourglass in the right hand, and a spear in the left pointed to a heart with three blots of blood.
Jack Rackham- active 1718–1720
Otherwise known a “Calico Jack”, Mr. Rackham had a simple yet kickass version of the skull and cross bones- exchanging the bones with a pair of swords. This flag was designed by his first mate Karl Starling.
Christopher Condent- active 1700s
Known by his fellow pirates as “Billy One-Hand”, Chris had this bad boy as his flag. Three skulls and three sets of crossbones on a black background that just screamed “Get ready for a serious pirate beat down.”
Christopher Moody- active 1713-1718
You don’t often think of a red flag when you picture pirates, do you? Maybe that’s why Chris decided to use it. The flag has a solid red background with a dark red flag with a golden hourglass winged in blue, a white arm holding a sword, and a golden skull & bones in the fly.
Edward Low- active c.1721—c.1724
I gotta say, this one is pretty damn intimidating. Originally, Low flew the same flag as Black Beard. However, after realizing that it was probably best he started using his own, he simplified his old one by removing the spear, heart, blood, and glass, and then painting the entire skeleton red. Hell yeah.
Emmanuel Wynn- active c. 1730
Emanuel isn’t the most memorable pirate, however, he is considered by many historians to be the first pirate to fly a “Jolly Roger” which is a flag that identifies a pirate ship. His flag contained a skull and cross bones over an hourglass.
Stede Bonnet- active 1717–1718
This flag is pretty awesome. It contains a skull over a horizontal one flanked by a heart and a dagger.
Thomas Tew- active 1692–1695
This flag strays away from anything resembling skulls and hearts by having a big ass arm holding a big ass sword. NICE.
Walter Kennedy- active ca. August 1718 – July 21, 1721
This one is as intricate as they come. The flag is black with a large skull and cross bones (which has a creepy face) next to a naked man holding both a sword and an hourglass. Odd? Yes. Wicked? Also yes.
