“Calico Jack” Rackham
The first record of Rackham participating in piracy comes from 1718, when he was quartermaster aboard Charles Vane’s ship Ranger. After Vane was removed from captaincy of the Ranger, Rackham was voted to the captaincy. He would command several vessels throughout his time as a pirate, most notably the Kingston. No matter which ship he commanded, Rackham would use the exact same flag: a skull above a pair of crossed swords (shown above).