LeFwee: Me pirate flower finally blooms! Yet ye'd favor this cripple over me? The smartest man on the Seven Seas?
Penelope: Oh, I do like smart guys... and he beat you at your own game. You tell me who's more intelligent.
LeFwee: Be still my heart and quick me blade... 'tis time for a duel! You and I'll make the mating dance of death!
― LeFwee and Penelope as she protects Bentley[src]
First of all, they decide to approach LeFwee's ship, by destroying the masts, but they must not sink the ship because Penelope may be on it. Then, Sly Cooper jumps on board and tries to tick LeFwee off, so that he can reveal Penelope's location. Unintentionally, LeFwee spills out that Penelope will never leave Skull Keep as she is locked in irons until she agrees to love him. Sly then jumps off the plank and into the boat with Murray, and they head towards the land. Murray drops Sly off at the dock and he tells Murray to keep the boat safe as they will need it for the escape. Sly makes the run for Penelope and several pirates chase after him. Once he gets to the top and opens the door, Sly finds out that it is an ambush, and LeFwee had tricked him, placing a fake Penelope doll with dynamite attached to it. It then blows up with Sly still inside.
Murray informs Bentley that Sly is all blown up and LeFwee's ship is gaining on him. Bentley, who is at the wheel, tell Murray to meet him at the mouth of the harbor. He plans to head into the deeper waters in an attempt to give LeFwee the slip, However, LeFwee and his mate spots them and they shoot down their masts. However, the waters are deep enough for Crusher, (who is still under the Guru's control), to enter the scene. As the beast rises up above LeFwee and his mate, the two become frightened and run off. The beast (who is still under The Guru's control) helps Bentley rescue Penelope, who is trapped under the deck. As he is trying to free her, several pirates come out on deck to stop him. The beast must smash them with its tentacles to protect Bentley.
Once Penelope is rescued, LeFwee returns to the deck and commands Bentley to call off Crusher or he will kill Penelope. Bentley tells the Guru to back off. Sly then arrives and tries to attack LeFwee, but he knocks everybody away and he gets kicked overboard and falls into the water. Bentley falls off of his wheelchair and tells the Guru to save Sly from drowning. LeFwee towers over Bentley and prepares to finish him off, but is halted by Penelope, who dons a pirate sword. It was now up to Penelope to fight LeFwee. The two fight starting at the top of the mast. After three rounds, Penelope eventually knocks LeFwee into the deep, cold water, causing him to get lunched on by the hungry sharks.
After Penelope's victory, she and Bentley grows closer together, as they can now demonstrate their feelings they have for each other.