The Death of Captain Shadow Sail

What If: The Death of Captain Shadow Sail is made by CaptainShadow11. Please do not copy its ideas / content without consulting Shadow here.

Thank you and enjoy the page!

'What If: The Death of Captain Shadow Sail is under construction by CaptainShadow11. Please do not edit this page unless it is a spelled or grammar issue.'More will be added to the page daily.

Thank you!


Midnight had fallen, and the beginning of yet another year had arrived. Shadow and some of his friends, John, Cortez, the prince of Italy, and Basil Bridgebain were in the wine cellar celebrating the new year. All in happy spirits, all having a good time, but what the three did not know was the extreme misfortune that was about to come upon them.

Chapter One - The Disturbance

As Shadow popped open a bottle of his finest rum for some of his finest friends, the three talked about the new year. "Aye, hopefully this year will be better then the last?" said Cortez hopefully.

"I have my doubts, Italy's economy is a fragile piece that many other countries seem to like to mess with," exclaimed Shadow.

"I'll shot throw a bottle of rum at their face and they will be.... what was I saying again?" said Basil... he was half drunk from the 10 or so glasses of rum he consumed.

"All I'm saying is it can't get much worse then last year, Shadow... it really can't." Cortez was referring to many pirates attempting to ruin Italy all together... from grenades, to swords, to blood fights, they found a way to keep Shadow up at night. As Shadow persuaded Cortez that they must not let their guard down, a butler walked in, handing Shadow a letter addressed to "Captain" Shadow Sail.... all letters were always made out to "King" Shadow Sail, in fact, it was considered very rude to refer to him as "Captain".

"Sir... there was a letter addressed to your informal name. You might want to see this...." said Stormwalker. The letter read:

Captian Shadow,

You don't need to know who I am, nor what I am here for. But, I am telling you vidal information. An unknown country is planning to bomb Italy. I happened to come across the plans, which involves 1,700 grenades and 100 cannons. If you don't understand the nature of this, let me spell it out. This attack could ruin Italy... all of it. If you want to save it, meet me at Port Royal, the Caribbean.

~ My name is not important

Stunned, Shadow showed his 3 friends.

"Its a scam most likely, don't let it ruin your new years," said Cortez.

"Agreed, its probably some teens playing a prank," John pointed out

"WHAT? Grenades?! I like grenades!!!!!" and with that, Basil, still drunk, took out his grenade pouch and blew up the wine cellar.


Shadow banned Basil from the wine cellar (and possibly the remainder of his house). But that was the least of his problems. He could not sleep new years eve. He could not eat, drink, entertain himself, anything. He just sat in his office thinking of the anonymous letter that arrived on New Years Eve. While he was thinking his friend John enters his office, worried about his friend. John asked why the letter was still bothering him, for, he thought it was a silly prank. But Shadow cared for Italy, as any King should, and he took the letter as a huge threat. So, what else could he do? He wrote back, after John pointed out that the Port Royal location meet could very well be an assassination or a trap.

To Whom Ever This May Concern,

I received your letter and it worries me deeply. I will not meet up with you, because that brings danger along with it, but I would like to know more details about this discovery. If you do succeed to reveal more about this, or find out, you will be rewarded greatly.

Thank you for your time,

King Shadow Sail


Days went by, then weeks, then months, months of no sleep and pure stress that was on Shadow's shoulders. He had not choice. He had to go to Port Royal as the letter had directed. He told the country of Italy that he was going on a "business" trip that may take a few weeks. Shadow invited 4 of his closest and most trust worthly friends. Cortez, John Breasly, Basil (dispite his foolish actions on new years), and one last person. Though they had not been real close friends, Shadow admired this person and looked up to him, for, he was loyal, nice and respectful to all he met, and he was a great fighter. His name was Lawrence Daggerpaine. The four were against the idea, but they stood by their friend. Their voyage (12 days it was estimated to take) started March 8.


"Oh what a lovely day in this world that we live in and we enjoy of the nature of the forests and all the stuffs!" Basil said. He had found the ships rum source. The SS Shadow II had a very large wine / rum cellar in the lower decks. Shadow locked these with 5 metal locks, however, Basil came prepared with a rock.

They were on their 5th day and the voyage was going smoothly. Shadow was captaining the ship (it was only him, his four friends, and a crew of 8, the voyage was suppose to be kept as secret as possible, thus, he brought a small fraction of the crew). John, Cortez, Basil, and Law were all sleeping that night. It was a peaceful setting. They were in a small moonlit cove appropriately named Moonlight Cove. The gentle waves touched the giant vessel one by one, and all was well, until a noice was heard.

==Chapter 2 - The Voyage==
Community content is available under CC-BY-SA unless otherwise noted.