Jack Sparrow

Captain Jack Sparrow's History
The son of the infamous pirate Captain Teague, and born on a ship in the middle of the Indian Ocean in the middle of a hurricane, Jack Sparrow was born to be one of the greatest pirates of all time. His enemies may call him a drunk, insane coward, but appearances can be deceiving...Jack always has a plan brewing in his head amidst all the rum, and always finds a way to win. Jack's exploits (although many have doubtless been exaggerated) are many, and he has seen and done almost everything. Captain Sparrow has been victorious against his mutinous undead crew, the ruler of the seas, Davy Jones, the powerful East India Trading Company, and has even come back from the dead. Although it is hard to imagine what Jack will do next, he will doubtless be ready, rum bottle in hand and smile on his face.

Battle
Captain Jack:

Captain Ash:

Captain Ash and four members of an expedition team are in a longboat, rowing to the shore of a tropical island. They get to shore and head inland, failing to notice a second, empty longboat also on the beach. Meanwhile, Captain Jack Sparrow and four crew-members are sitting in a campsite, drinking and talking amongst themselves. One crewman hears something in the bushes, grabs his musket, and goes to check it out.

Seeing Ash's team approaching, the pirate fires, killing one of Ash's men. The pirate tries to reload, but Ash opens fire with a K-SMG, spraying the attacker with lead. Alerted by the gunfire, Jack and the remaining pirates get their weapons and head off into the jungle. Ash's team reaches the pirate camp, which is apparently abandoned. Suddenly, a pirate rushes out with a boarding pike, and stabs one of the team. The man nearest shoots the pirate with his blunderbuss, but the remaining team-members are shaken. Ash cheers up his men, and they head off into the jungle.

Coming upon an abandoned mill, Jack and the two remaining pirates set up an ambush. One of the pirates lays in wait by the entrance. As Ash's team approaches, he shoots at them with his pistol, but misses. Ash and his crew fire back with K-SMGs and Kruger 9mms, but have similar luck. Ash readies his flare gun and fires at the doorway. The pirate sees the flare streaking towards him and yells, but he is too late. Ash and his team move in and find another pirate at the top of a flight of stairs. The pirate shoots and kills one man, and pins down Ash and the other. Thinking quickly, Ash straps some dynamite to the bottom of the staircase. They flee as the dynamite explodes, taking out the pirate.

Thinking they have killed all the pirates, Ash and the final remaining man head back to the longboat. As they arrive, however, they are confronted by a nasty surprise...a lit grenado in their boat. It explodes, taking out the final member of Ash's team. Ash, who was further away from the boat, survives the blast, but is left dazed. Laying on his back, he reaches for his Kruger 9mm, but a boot pins down his arm. Ash looks up to see Jack grin, before the pirate captain stabs his cutlass into Ash's heart. Jack takes a bottle of rum from his belt, uncorks it, and drinks before heading back to his own longboat.

Expert's Opinion
Captain Ash, while not very well known, got more than a few votes due to his modern weapons and military background. However, Jack's supporters believed that the pirate had his cunning in his favor, and would have surprises that Ash simply couldn't match.