Kokonoe: Pirates... sometimes I can't tell if they're incredibly smart... or just completely insane. One thing's for sure though... these two are legends across the sea.

Junko: Captian Edward Kenway, the Pirate Assassin!

Ann: And Captian Jack Sparrow, the madman of the Caribean!

Kokonoe: The stage is set and the combatants are ready.

Junko: It's time for a Death Battle!

Floating in the great seas of the Caribean, Captain Jack Sparrow sailed the Black Peral, looking through his spyglass as his attention focused on a ship not too far from his. 

Gibbs: Captian! Where shall we set course?

Sparrow looked at his campus and saw that it pointed straight at the ship. Jack closed it and looked among his crew.

Jack: Follow that ship men! Those men have something I want.

Jack's Crew: Aye!

Meanwhile, on the Jackdaw, Captain Edward Kenway sailed with his crew as his first mate, Adewale, walked toward him.

Edward: How's it looking?

Adewale: Smooth sailing so far. It seems like a storm will be brewing soon... and that ship behind us has been following us for quite some time. I do believe they mean business.

Kenway turned to see the Black Pearl coming in close.

Edward: Business huh? Then let's give them a little business of our own. Drop the barrels!

Edward's Crew: Aye!

Four barrels were dropped into the water. Jack noticed this and immediately tried to turn the boat away. But it was too late as the barrels blew up under the ship the moment they made contact, rocking the Black Pearl. The Jackdaw then made a sharp turn as it circled around and managed to get right beside the Black Peral. Everyone on both sides was prepared to enter battle.

Jack: Hold it! Wait just a sec!

Jack stepped in front of his men and they held their ground. Edward stepped in front of his men as well to see what was going on.

Edward: What's the holdup boys?

Jack turned to see Edward standing on the side of the opposing ship.

Jack: Ah, so you must be this Edward Kenway people are talking about.

Edward: That's right. And you're Jack Sparrow?

Jack: Captain Jack Sparrow and yes. Now as far as I'm concerned, we went after you, you attacked us, and would definitely outnumber us. But fret not, if you surrender to me now I will let you live.

Edward: I'm not sure that's how this works. Maybe if you surrender to me, I'll be sure to let your crew live without you.

Jack: Ah. Well in that case boys, I suppose we should carry on. 

Edward: Alrighty men! Take battle stations!

Gibbs: You heard him! Let's get ready for a-

Thunder was heard from above as it slowly started to rain.

Edward: Adewale, take the wheel!

Adewale: Aye sir!

As his first mate took the wheel, Edward jumped onto the Black Pearl, killing two pirates by stabbing them in the neck with his hidden blades. He looked up to see Jack running away. He took out his blowpipe and shot a dart at Sparrow. The dart nearly hit him, but missed and hit the mast instead. Jack saw that and looked back as Edward was approaching him.

Jack: Well that's not good.

https://youtu.be/5XpbhMw2408

Edward pulled out one of his blades and swung it as Jack quickly dodged. He took out a sword of his own and swung it, but Edward blocked the strike, took out his other blade, and swung it as well. Jack dodged it and swung his sword again, but Edward blocked it and went for another swing of his own. Jack jumped back to dodge that as well. Edward kept going for strikes and Jack kept dodging them before going for another strike and knocking one of the blades out of his hands. Before Sparrow could go for another strike, Edward swung his sword and knocked Jack's blade out of his hands.

Jack: Uh oh.

Edward went to stab him and Jack jumped to the side to dodge it, causing the blade to get stuck in the mast. Both captains pulled out their pistols and quickly aimed their guns at each other.

Jack: Well now, it seems you've come prepared.

Edward: A wise man always does.

Suddenly, the rain and winds grew heavier as the Jackdaw bumped into the Black Pearl, causing the ship to shake as both Edward and Jack fell to the ground, dropping their pistols. Jack saw a peanut on the floor and quickly ate it before they both looked up to see one of their pistols was on the other side o the ship. They looked at each other then back at the pistol before running after it. Jack pushed Edward to the side before jumping down and grabbing the gun. He aimed the pistol and fired at Edward, and Edward jumped to the side to dodge it. Jack went for another shot but the gun was already out of ammo so he threw it to the side. He then looked up to see Edward jumping down ready to stab him with his hidden blade.

Jack: Woah!

Jack quickly rolled out the way and dodged Edward's attempt before getting up and running away. Both ships then rocked again as Edward noticed they were going faster.

Pirate: Whirlpool!

As the storm grew heavier and thunder grew louder, the pirates found their ships swimming around a powerful whirlpool.

Edward: Dammit!

One of Jack's pirates then tried to sneak behind Edward and swung his axe at him. Edward saw it coming and quickly used his wrist blade to stab the pirate in the throat before taking his axe and using his Eagle Vision to track Sparrow down.

Captain Jack Sparrow was still running. He turned to see Edward jumping at him and swinging his axe. Jack managed to jump and dodge the attack before Edward swung it again. Jack got back and grabbed a barrel as Edward went for a downward swing. Jack then took the barrel and used it to block the axe. He kicked Edward back and tossed the barrel at him before running towards the other ship. Before he could jump onto the Jackdaw, a pirate swinging on a rope accidentally bumped into him, causing them both to swing on the same rope. Jack looked and saw the pirate before immediately taking the man's pistol.

Jack: Mine now.

He knocked the pirate off and as he swung on the rope, he aimed the gun. Edward realized what he was doing as he dropped the barrel and ran. Jack fired a bullet and shot at the barrel, causing it to explode as Edward jumped onto the Jackdaw. Meanwhile, Captain Jack Sparrow swung onto the ship's sails. As he tried to keep his balance, he saw one of Edward's men up there with him. He aimed his gun but there were no bullets.

Jack: Huh. Two times in a row. Well that's a little awkward now, isn't it?

The other pirate went to swing his sword but Jack then breathed in his face. It smelled so bad the pirate passed out.

Jack: Oh, I'll be taking that.

He took the pirate's sword before the man fell. As he did, Edward grabbed the sword of a dead irate and pulled a hook that brought him all the way up to where Jack was. They both managed to keep their balance as Jack went to face him again.

Jack: You're skilled, I'll give you that much. But let's see you're footwork!

They both swung their blades and clashed. Jack went for another swing and Edward leaned back to dodge it. After that, they both swung their blades again and clashed another time. Edward then pulled a backup pistol out of his coat and shot at Jack, who dodged the bullet just barely.

Jack: Woah!

Edward swung his blade, but before he could cut him, Jack had already fallen off the sails. He quickly grabbed a rope and managed to crash onto the boat safely. Edward dived down and threw a hook at the sails to break his fall. Jack saw this and got up as Edward jumped off the mast of the ship. Jack pulled out a backup pistol of his own and shot Edward in the leg, causing him to crash land right behind him. Jack turned around and pulled out his sword as he walked toward Edward.

Jack Ha! Remember this day my son! For it is the day you almost caught... Captain Jack Sparr-

He lifted his sword and Edward quickly threw a throwing knife that went right through Jack's neck.

Jack: -ow!

Edward then used both his wrist blades and stabbed Jack in the gut. As Jack fell, both the Black Pearl and Jackdaw swam out of the whirlpool. Though both ships survived, Edward's crew ultimately won as Edward himself laid beside the dead captain. The storm was over as sunlight beamed on him and he listened to the cheers of victory coming from his crew.

Junko: I'll be the first to admit, we kinda improvised with this. Not because we didn't know what we were doing, but because it was really tough calling this one.

Kokonoe: Both these combatants were surprisingly even in their fields. Both are highly intelligent on the inside while looking like madmen on the outside. 

Ann: As far as ships and crew go, Jack definitely had the better ship. But Edward had him severely outnumbered. Though this wouldn't matter much since Jack's used to those odds himself. And while Edward was better with a blade, Jack had shown to be skilled enough to take on swordsmen far better than himself. 

Kokonoe: Still, Edward's more vast arsenal helped him get the edge he needed. Jack may be the type to play dirty, but  Edward already has a vast amount of experience taking on guys like that. And while Jack is certainly more durable than Edward, he can still be killed through relatively normal means.

Junko: It was quality vs quantity and in this instance, Quantity finally won! Looks like Jack's luck ran out against a Kenway.

Kokonoe: The winner is Captain Edward Kenway.

Winner: Edward Kenway:

+Larger Arsenal

+More skilled

+Larger crew

= Intelligent

=Reckless

=Tricky

=Equally Drunk

=Experiance

= Near Equal Speed

-Less Durable

-Weaker Ship

-Not Johnny Depp

Loser: Jack Sparrow

+Johnny Depp

+Stronger Ship

+More Durable

= Intelligent

=Reckless

=Tricky

=Equally Drunk

=Experiance

= Near Equal Speed

-Smaller arsenal

-Smaller crew

-Less skilled

Junko: Next time on Death Battle!

https://youtu.be/soSSJHxxxXU

Nui Harime vs Neopolitan

(Kill la Kill vs RWBY)