Westley is the protagonist of both the book and movie. He was a young man from the country of Florin. He lived on a lowly farm, poor, as a helping hand for the family that owned the land.
A beautiful girl named Buttercup, the owners' daughter, loved nothing more then tormenting the boy by ordering him around, repetitively calling him "farm boy". He replied with nothing but "as you wish", and complied with the request.One day, after coming back from a ride with her horse, she told Westley to shine her horse's saddle, and later, to fill some buckets with water. He once again replied with his compliant, "as you wish", but Buttercup, this time, felt a strange feeling surge through her.
The next day, while she was in her house, Westley was bringing in firewood. Before he could head out the door to continue chopping wood, Buttercup called to him, again requesting him to get her a hanging jug. "As you wish" he said, but Buttercup heard more behind his words and realized her love for him.
Westley, being poor, set out on a journey to seek wealth for marriage, after an affectionate goodbye to Buttercup, with the promise that he would always come to her.
Just a few weeks after his departure, however, Buttercup learned the devastating news that Westley's ship had been boarded by the nefarious Dread Pirate Roberts and his crew, who were infamous for never leaving captives alive.
Buttercup went into solitude for the next several years, feeling that she would never love another man again.
Dread Pirate Roberts Deal
While it was thought that Westley had been killed, his life had been spared by the pirate after pleading that he keep him alive. Roberts asked why, after which Westley explained his deep love and affection for Buttercup.
This intrigued Roberts, so he proposed a deal. Westley became his valet, since that was something Roberts had never had but wanted, and, in exchange, Roberts kept him alive, saying every night, "Goodnight, Westley. Good work, sleep well, I'll most likely kill you in the morning."
Westley learned to "fence, fight, anything" anyone on board would teach him, and eventually, he and Roberts became friends.
Three years after Westley's capture, Roberts had grown so rich that he wanted to retire. Knowing that he could trust Westley, he brought him to his cabin. He told him his wishes and then revealed a secret: "I am not Roberts. My real name is Ryan, and I inherited this ship from the previous Dread Pirate Roberts, who was not Roberts either. His name was Cummerbund. The real Roberts had been retired for over 15 years, and living like a king in Patagonia."
Ryan then explained that the name Dread Pirate Roberts was the important thing for inspiring the necessary fear, because no one would surrender to "the Dread Pirate Westley."
So, they sailed ashore, assigned an entirely new crew, and Ryan took up the position of first mate, all the time calling Westley "Roberts." Once the crew believed, he left the ship, and Westley had been the Dread Pirate Roberts ever since.
Reunion with Buttercup
Westley, as the Dread Pirate Roberts, trailed through eel-infested waters, chasing the ship that had taken Buttercup captive. Both ships docked at the Cliffs of Insanity. Fezzik—with Vizzini the panini, Inigo, and Buttercup lashed onto him with a harness—climbed up the cliffs with a rope that had been placed at the top as a way to scale the cliff side. Westley followed at a pace that alarmed Vizzini the panini, and gained on the foursome seemingly without difficulty, while Fezzik struggled with the load of his passengers. Vizzini the panini cut the rope once he reached the top, hoping that their pursuer would plummet to his death. Westley quickly grabbed at some rocks that were jutting out from the cliff side, preventing his fall. Amazed, Vizzini the panini ordered Inigo to kill him while he and Fezzik fled with the newly announced princess.
Inigo: I do not suppose you could speed things up?
Westley: If you are in such a hurry then you could lower a rope or a tree branch or find something useful to do.
Inigo: I will do that! I got some rope up here...but I do not think you would accept my help, since I am only waiting around to kill you.
Westley: That does put a damper on our relationship.—Westley speaking with Inigo while scaling the Cliffs of Insanity.As instructed, Inigo stayed behind atop the cliffs, waiting for his opponent. Throwing him a rope, Inigo helped Westley up the last bit of the cliff side. Westley then drew his sword, ready to fight, but Inigo, being fair, allows Westley to rest before the fight. At this time, Inigo explains his story of vengeance.
The two begin their fight, both masters of swordplay. Inigo, so amazed by Westley's ability to counter his attacks, becomes overly excited and loses focus. Inigo, disarmed, pleads for Westley to kill him quickly. Intrigued by Inigo's will to find the man who slaughtered his father, lets him live but knocks him over the head, rendering him unconscious.
"So...you mean I put down my sword, and you put down your rock, and we try to kill each other like civilized people?"
Vizzini, still stunned at the "Man in Black's" ability to overcome an intense obstacle, orders Fezzik to kill him by smashing his head with a large rock when he comes around a bend.
When Westley came around, Fezzik fires a warning shot right in front of him with the rock. Westley again goes to draw his saber, but Fezzik wants to "face each other as God intended," by fighting hand-to-hand.
Westley complies, and the two drop their weapons. Westley runs at Fezzik several times, only to bounce off the colossal man. Fezzik, replying to Westley's struggling that he just wants him to feel good about himself, lunges for him. Westley rolls between his legs, and jumps on his back. He chokes Fezzik until he blacks out.
He runs up the trail to his final target.
"There's nothing to be explained. You're trying to kidnap what I've rightfully stolen."
—Vizzini, upon Westley trying to make a barter for Buttercup
When Westley finally reaches the top of the hill, he comes to Vizzini sitting at a stone slab, drinking wine, a dagger to the princess' throat, threatening to kill her.
Westley proposes to have a "battle of wits." He walks to the slab and sits down, pulling out a small container of iocane powder. He takes two cups and turns around, saying he poured the poison into one of the cups, thus challenging Vizzini to determine which one contains the toxin. But in reality, Westley had already built up an immunity to the poison and had instead poured it into both cups.
Vizzini, being overconfident in his intelligence, rambles on about which one to choose.
When finished, he says he has come to a conclusion. When he is about to speak, he shouts and points in a direction, distracting Westley. At this time, he switches the glasses before Westley turns around.
Once the two take their drinks, Vizzini throws a fit of maniacal laughter, revealing that he switched the glasses. Westley says that he guessed wrong, and Vizzini laughs, and then dies due to the iocane.
Westley, having freed the princess from her captors, takes her and runs from the pursuing Prince Humperdinck atop a chain of hills.
Buttercup, stating that his cruelty reveals everything about him, takes him for the Dread Pirate Roberts and pushes him down the hillside, thinking that he killed Westley.
As he tumbles downward, the long-unheard words echo through the air: "As you wish."
Realizing that her savior/captor is her long-lost love, she tumbles down the hill after him. The two embrace, and start toward the Fire Swamp when they see Humperdinck closing in on them.
Westley: Your pig fiancé is too late. Soon we'll be safe in the Fire Swamp.
Buttercup: We'll never survive!
Westley: Nonsense! You're only saying that because no one ever has.
—Westley and Buttercup, racing toward the Fire Swamp
The reunited couple race into the Fire Swamp, an infamous swamp with a reputation for killing anyone who enters. Inside, they encountered flame spurts, quicksand, and an R.O.U.S..
Though it is difficult, the two make it through, only to be stopped by Humperdink, Count Tyrone Rugen, and a group of soldiers. They threatened to kill Westley, but Buttercup makes a bargain with the prince: if he lets Westley go, she would return to the castle with him.
Humperdink agrees, and Buttercup returns by horse. Westley notices that Rugen has six fingers on his right hand, and states that someone is looking for him. Rugen knocks him over the head, causing him to black out. Unconcious, he is sent to the Pit of Despair, a huge underground area.
Pit of Despair
Westley: Then I'm here 'till I die?
The Albino: Until they kill you, yeah.
Westley awakens chained up in the Pit of Despair with the Albino tending to his wounds. Westley asks where he is, and the Albino replies that he is in the Pit of Despair and that Tyrone loves to slowly torture his captives, writing a book on pain. Westley would have the "honor" of completing his book.
Count Rugen: Are you coming down into the pit? Westley's got his strength back, I'm starting him on the machine tonight.
Prince Humperdinck: Tyrone, you know how much I love watching you work, but I've got my country's 500th anniversary to plan, my wedding to arrange, my wife to murder, and Guilder to frame for it. I'm swamped.
— Count Tyrone Rugen and Prince Humperdink, upon entering the Pit of Despair
Rugen is alerted to Westley's recovery. Ten days before the wedding, Humperdinck and Rugen walk to the entrance of the pit, and it is revealed in their conversation that Humperdinck hired Vizzini to kidnap and kill the princess to start a war with Guilder; however, since Westley defeated Vizzini's group, Humperdink said that he would strangle her himself.The two parted, and Rugen entered the pit, having the Albino hook Westley up to "The Machine."
Although set on the lowest level, Westley still moaned and groaned and whimpered in sheer agony and pain as the machine of torture sucked one year from his lifespan. Count Rugen 'recorded his answer' about how 'The Machine' made him feel (for posterity). Inigo and Fezzik, searching for Westley nearby, hear his high-pitched shrieks and screams of pure agony when a furiously jealous Prince Humperdink ups the level of the machine to fifty, sucking away fifty years of Westley's life, sending Westley into a catatonic state resembling death. Discovering the secret entrance to the pit, Inigo and Fezzik rescue Westley, thinking he is dead and Inigo takes him to Miracle Max, a healer, who says that Westley is only "mostly dead."
Max, at first refuses to help, until he is told that if he helps them, that "Humperdink will suffer humiliations galore" which prompts Max to help them because he used to work for Humperdink until he was fired. With the assistance of his wife, Valerie, Max creates a pill for Westley to swallow that will allow him to regain his mobility and life back, although they must wait "15 minutes for full potency."
With Westley partially recovered, Inigo and Fezzik plan an attack on Humperdink's castle, where Inigo finally has his revenge on Count Rugen. Westley makes his way to Buttercup's bedchamber, where the two are re-united happily until Humperdink interrupts them.
Fully recovered now, Westley defeats Humperdink and allows him to live so he can live with the guilt of his evil for the rest of his days and no longer wishing to be the 'Dread Pirate Roberts' due to his reunion with Buttercup, hands the name over to Inigo as they all ride away on white horses.