'Calico' Jack Rackham

"Calico" Jack Rackham is remembered more for his favorite clothing and his female crewmembers than for his mediocre accomplishments as a pirate. His nickname is for the cheap and brightly colored cotton clothes he was fond of.
One of the first references to him finds him as quartermaster for Charles Vane's operation out of New Providence, Bahamas in 1718. Late that year, Vane fired on a French vessel that he then discovered was a warship. Although he felt discretion and retreat was the better part of valor, his crew disagreed, and the next day he was sent off after Rackham was elected captain.
Read more at The Pirate's Realm.