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Jack Sparrow has Buttercup on the Black Pearl.

Westley is after her, obviously, and is in his much faster ship.

Westley catches up to the Pearl and engages in combat with Sparrow.

Scenario 1) Sword fight to the death. Fencing only.

Scenario 2) Sword fight with h2h mixed in. Anything goes. To the death.

Scenario 3) The Black Pearl docks at port on an island and now Westley and Jack have to fight on an open beach. Same rules as #2.

Mmmmmmm.......Westley I think. He seemed more impressive to me.

cap for all 3

Westley defeated the Spaniard quite elegantly. To me, he would be better with a sword. He managed to put down Andre the Giant with a sleeper hold..so, I believe Westley could win a H2H fight. Westley also won a battle of wits, so I think he has the right tools to outsmart and outfight Sparrow.

first one I give to wesley, I'd say he is the better sword fighter, considering how easily he defeated inigo. Second fight could go either way, but I'll give the edge to jack, simply because they're fighting on a ship that he knows well, and the third I give to Wesley, I don't think Jack has any obvious advantages on a beach

Originally posted by Tattoos N Scars
Westley defeated the Spaniard quite elegantly. To me, he would be better with a sword. He managed to put down Andre the Giant with a sleeper hold..so, I believe Westley could win a H2H fight. Westley also won a battle of wits, so I think he has the right tools to outsmart and outfight Sparrow.

Jack fought evenly with Davy Jones....an immortal being who'd been around for hundreds of years at least. I say that makes him a pretty uber swordsman, and that Jack fought him and didn't die speaks volumes.

Originally posted by Tattoos N Scars
Westley defeated the Spaniard quite elegantly. To me, he would be better with a sword. He managed to put down Andre the Giant with a sleeper hold..so, I believe Westley could win a H2H fight. Westley also won a battle of wits, so I think he has the right tools to outsmart and outfight Sparrow.

This is correct and covers it well.

Originally posted by KingD19
Jack fought evenly with Davy Jones....an immortal being who'd been around for hundreds of years at least. I say that makes him a pretty uber swordsman, and that Jack fought him and didn't die speaks volumes.
Jack also spent a good portion of that fight running, if memory serves me correctly. And just because Davy Jones has been around for hundreds of years it doesn't mean he's been practicing his swordsmanship, why would you when you've had the kraken to do all your dirty work for you

Originally posted by General_Iroh
Jack also spent a good portion of that fight running, if memory serves me correctly. And just because Davy Jones has been around for hundreds of years it doesn't mean he's been practicing his swordsmanship, why would you when you've had the kraken to do all your dirty work for you

And are immortal.

Westley allows Jack to think he has the upper hand in all three scenarios until he reveals he is not left handed. 313

Honestly, without access to his pistol to at least distract Westley, I don't think Jack can win.