Jack Sparrow woke up with the surf washing over his body. His body was covered in sand and soaked to the bone. It was not an unfamiliar feeling. He slowly hauled himself to his feet and looked around. The shoreline curved away in either direction, leaving the impression that this was a relatively small island. Inland, the island was lush with vegetation and tall trees. Jack looked around for his belongings and found his pistol and sword nearby. His compass remained his pocket, but his rum was nowhere to be found. Suddenly, a voice boomed in his ears.
“Welcome, champions, to my island! I hope for a good fight from the two of you… who will be the greater pirate, I wonder? Please, don’t disappoint me… the only way home for either of you is to defeat your opponent! Best of luck!”
The voice cackled and grew silent. Jack grumbled and pulled out his compass, thinking of how badly he would like to be anywhere but here. It pointed into the interior of the island… hopefully towards his target. With one last look on the beach for his rum, he headed in the direction the compass indicated.
Across the island, Westley also heard the voice. He had woken up dressed in his Dread Pirate Roberts clothing and with his sword buckled to his hip. He had no intention of letting his opponent, whoever he may be, keep him from Buttercup. He charged into the forest with his sword drawn and began the hunt for his enemy. Questions about his predicament surfaced in his mind, but he quickly pushed them away, preferring to deal with them later, when he was safe. The jungle in this area was thick, forcing him to swing his sword to clear the path. Perhaps if he left obvious enough a trail, his opponent would fall into his hands quickly and this would be done with. Soon Westley found himself in a small clearing. “This will do nicely. Now, we simply must wait,” he spoke softly, to himself.
Jack continued to follow the compass and soon happened upon a clearing. In it stood a man in black, with his eyes peeking out from two small holes in a bandana. He was unaware of Jack, for the moment. Jack crept slowly closer until he was at the edge of the meadow. He positioned himself behind his masked foe and then leaped into the open, pistol drawn. “Sorry, mate. Good try and all that,” he said, with a grin.
Jack pulled the trigger.
His enemy had found him before Westley even had time to prepare. It was impressive. He stared down the barrel of the pistol and saw his foe’s finger squeeze the trigger. The gun clicked, and went silent. The grin on the face of the man wielding it faltered and then fell. He turned the gun around and looked at it. “Oh.” He said, softly. Westley gathered his wits and wasted no more time. He charged, sword drawn and attacked. His target dropped his pistol and quickly drew his own sword. They exchanged blows, and Westley soon realized that his opponent was rather adept with the sword. “You’re not too bad, my friend. What is your name?” asked Westley, after a particularly swift deflection.
“Name’s Captain Jack Sparrow. Don’t suppose you’ve seen my rum anywhere, hm?” came the reply.
Westley laughed loudly as he performed a quick riposte, but Jack moved and avoided the counter. “And I am the Dread Pirate Roberts,” answered Westley, “You’re quite good with the sword, Captain Sparrow. But I’m afraid that there is one thing you haven’t accounted for.”
Jack swung his sword in a heavy overhand arc. “Rest assured that I’ve taken your terrible facial hair into consideration and attacked accordingly.”
Westley chuckled and avoided Jack’s attack by leaping backward. “Not quite. The truth is… I’m not really left handed,” Westley said as he tossed his sword into his right hand.
Jack took a moment to breathe while his opponent showed off. His damned pistol had gotten too wet and soaked the cartridges, ruining his chance to end this early. Now he was stuck in a bloody duel. And this ‘dread pirate’ was easily the better swordsman. Once Roberts swapped his sword hand, Jack also spoke, “Well, there’s something you’re not accounting for either!”
“And what might that be?” asked Westley, with a grin.
The bloody maniac was enjoying this. Jack flashed his best smile, flourished his sword, and turned around and ran. He ran towards the beach, screaming every step of the way. When the jungle finally cleared away, he stepped onto the sandy beach and tripped, tumbling through the sand until he slowly came to rest next to his sword.
Westley had certainly never met a man like this Captain Sparrow before. He quickly followed behind the screaming madman and watched with pity as he tripped into the sand. He picked up his opponents sword and tossed it to him. “Come on,” he chided, “Up you go, let’s finish this.”
Jack fumbled on the ground for his sword, weakly. As he stumbled to get up, Westley waited patiently. Suddenly, as the downed pirate struggled to his feet, he pitched a fist full of sand at Westley, momentarily blinding him. He anticipated the quick attack, luckily and felt his sword resonate after the block. He attempted to regain his senses while his enemy attacked.
Jack knew he was desperately outmatched, but he still had his wits; well… and his ruthlessness. He attacked quickly and violently, hoping to catch his opponent off guard. He swung once, twice and on the third attack, succeeded in knocking his opponent’s sword away. It landed with a soft thud in the sand not far away. Jack grinned while Roberts rubbed his eyes. “It’s been fun, but in all the seven seas, there is no pirate who can match Captain Jack Sparrow,” gloated Jack, as he raised his sword.
He dropped it and it buried itself deep in the sand. Roberts had rolled away just before the attack. Jack sighed and turned to attack again.
Westley was now without a weapon, so he resorted to his training in hand to hand combat, which was not insignificant. This Captain Sparrow was no Fezzik, that was for certain. He dodged a second attack, ignoring the pain in his eyes. He slowly moved toward his sword, while dodging attacks made by the oddly dressed pirate. It had nearly buried itself in the sand and was rather hard to see. Westley stepped backward, heavily, sending sand flying in the air. It covered his sword, leaving it almost completely invisible. When Jack made his next attack, Westley jumped backward and caught his opponent’s hand at the wrist and held it above both their hands. Jack pushed downward with all his might.
Westley began to shake from exertion and stepped backward. The other pirate continued to press him and slowly forced him to his knees. He smiled as he realized he had the advantage and that Westley was tiring out. “Well, my new friend,” said Jack, “It’s been enjoyable. I hope you agree. Perhaps we can do this again sometime. In the meantime, however, this will be the day that you will forever remember as the day you almost beat Captain –
Westley let go of Jack’s hand and reached into the sand where his sword was hidden. Jack’s blade bit deeply into his arm, but threw Jack off balance and he pitched forward. At the same moment, Westley raised the point of his rapier into the air with his right hand and pulled his left shoulder backward, pulling the sword that had buried itself in his arm and throwing Jack even more off balance. The rapier pierced Jack through the abdomen.
Before Westley even had a chance to move away, Jack disappeared. Westley remained, kneeling in the sand bleeding profusely and panting heavily. The voice that had spoken earlier boomed once more.
“Excellent job! You showed both strength, skill and cunning to achieve your victory and outsmarted and outfought your enemy. Very, very, good… rest now, champion. Until I call upon you once more.”
Once more, the world went dark.
While dear Captain Sparrow is an excellent pirate, he is simply not the better fighter. Westley/Roberts is virtually undefeated (at least during the events of Princess Bride) and dispatched the Spaniard, the Giant and the Sicilian in a row, and he even managed to pull off that tiny little mustache. The Dread Pirate Roberts wins.