A List of The 10 Worst Pirates of All-Time*

Written by Fannin Fabriano

Sunday, 9 February 2020

image for A List of The 10 Worst Pirates of All-Time*
This is the skull & crossbones flag that flew on Itchybeard's pirate ship, "The Caribbean MoFo"

1. Timmy The Timid – Timmy stood 6 feet 4 inches, and only weighed 107 pounds. He was once beaten up by a skinny mermaid. He once dated Blackbeard's sister Esmeralda for two weeks.

2. Lorenzo The Lost – He retired at the age of 81, having never learned the difference between the Greater Antilles and the Lesser Antilles, or Austria and Australia.

3. Simon The SOB – The Simster, as his maternal grandmother called him, was notorious for his high seas pranks which included sticking live sardines in the underwear of his crew members as they slept.

4. Gay Gabriel – He wore a pink eye patch, and was noted for going around saying things like "Hey, lads, scupper me uppers, and don't overlook me lowers." He occasionally dated Jean Lafitte's younger brother, Sylvester.

5. Barnacle Nose Norman - The story is that even the cheapest prostitutes in the Bahamas wouldn’t touch him with a 10-foot pole.

6. Dina The Diva (Female) – She was a 217-pound butch lesbian who totally loved assuming the male buccaneer role. She also had a pronounced moustache, and was constantly spitting.

7. Captain Itchybeard - Old Itchy was a great pirate leader who knew a lot of the tricks of the buccaneer trade, but no one liked to get too close to him because of his constant crotch scratching.

8. Lipstick Leo - One of the first known cross dressing buccaneers. He wore a fuchsia pirate hat, ruffled panties, and his peg leg was decorated with lavender ribbons and sequins.

9. Seasick Sal – Salvador Cabeza de Toro had a hell of a time keeping anything down once his pirate ship left port. He was also allergic to tuna fish sandwiches and porpoise pizza.

10. Ying Yang The Confused – Y.Y. used to say that he wanted to be a karate instructor, a rickshaw repairman, or a chopstick salesman. He knew over 400 pirate songs, including the highly popular Bermuda buccaneer song “I Kissed Her Treasure Chest and She Kissed My Plank.”

*As compiled by The Chicago Daily Wind Newspaper.

The story above is a satire or parody. It is entirely fictitious.

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