Ilana is in hospital with her face heavily bandaged. Jacob visits her and they speak in Russian. Ilana is very happy to see Jacob who asks for help. Jacob explains that there are six people that she is to protect, and that their names will be on his list. He explains that this is what she has been preparing for and that the six are the remaining candidates.
Sometime later Ilana is speaking with Jacob. She no longer is bandaged. She asks what she should do after she has brought "them" to the Temple. Jacob tells her to ask Ricardus who will know what to do next.
Tenerife, Canary Islands - 1867
Richard Alpert rides his horse back to his remote house at Socorro and enters. His wife, Isabella, is lying with a high fever and coughing blood. Richard decides to get the Doctor and worries about not having enough money for his fee, so Isabella gives him her golden chain and crucifix and tells him to give it to the doctor. Richard is hesitant to take it but she asks him to close his eyes and closes his hand around the chain. She whispers that they will always be together and kisses him on the cheek. He promises he will save her and departs.
Richard rides through a storm to the doctor. The doctor lives in an opulent manor and is having dinner. Upon seeing Richard coming in soaked, he orders his butler to bring him some blankets, Richard tries to thank him but the doctor replies the towels are not for him but for the floor he's dripping water over. Richard tells him about his dying wife but the Doctor looks disinterested and says he won't ride for half a day under the storm. When Richard begs, the Doctor says that he has some medicine which can save the woman's life but remarks how expensive it is. Richard gives him all his money and when the Doctor asks contemptuously if that's everything, he also gives him the crucifix. The Doctor examines it for a second and throws it away saying it is worthless. Richard picks it up and pleads with him and they grapple. As the Doctor tries to push him away, Richard accidentally pushes him causing his head to bump against the side of a nearby table, and the Doctor falls dead. Richard stares in horror but as the butler appears in the door with the towels, he realizes he had secured the phial of medicine from the Doctor's hand in the struggle and runs out past a startled butler. Back at home he finds out that he's late and Isabella has died. He kneels down in pain as the constabulary burst through the door.
In jail, Richard is visited by the priest, whom Richard tells he has taught himself English and dreams of moving to the New World. However, the priest refuses to forgive his sin of murder, and tells Richard he will be executed the next day. The following morning, Richard is blindfolded and led away to be executed when he is stopped by Jonas Whitfield, an officer of a ship. The officer questions Richard about his English and willingness to work, then purchases Richard as a slave for Magnus Hanso .
On the Black Rock, Richard and other prisoners are in chains below deck while the ship is caught in a terrible storm. The other prisoner looks out of the cracks in the ship and tells Richard he sees land. The man then sees the Statue of Taweret and he shrieks that he sees the devil. The ship is thrown against the statue and comes to rest inland.
Richard and his fellow captives awaken to daylight. Five officers remain alive. The recruiting officer comes below deck and proceeds to kill the captives one by one with his scabbard. He tells him they have no water and limited supplies and it would only a matter of time before Richard attempts to kill him. Just as he is about to kill Richard, the black smoke arrives above deck and after screaming and turmoil there is silence. Finally the black smoke takes Whitfield and draws right up to Richard's face. The smoke examines him and leaves.
Still chained, Richard begins to loosen a nail from the floor. Over time he removes the nail and uses it to gouge around the chain fixture on the wall. He passes out and comes to when a boar in the hull disturbs him. The boar is munching on the remains of one of the dead captives. He loses the nail and passes out again. Isabella appears to Richard. She tells Richard that they are dead and in hell and that she has come to save him before the monster returns. As she tries to free him the monster returns and Richard demands she escape. She runs off and the smoke monster seems to take her as she resists, screaming. Richard is devastated.
Some time later, a man comes to Richard and says he's a friend. Richard asks after Isabella and explains what happened and the Man in Black says that "he has her". When Richard says he wants to be free the Man in Black says he does too. He has keys but wants to know that Richard will help him and do anything he asks before he frees him. The Man in Black unlocks the chains and when Richard thanks him the Man in Black says "it is good to see you out of those chains".
As the Man in Black carries Richard out of the Black Rock he says to Richard that the only way to escape from hell is to kill the Devil.
Richard eats a pig roasted on a spit. The Man in Black directs him to the statue, now broken into pieces, and tell him that is where he will find the devil. He gives him an ornate knife saying that Richard has one chance, that he cannot hesitate or let the devil speak because he is very persuasive. Richard asks how he can kill him as he is black smoke. The Man in Black says he is not because he is the black smoke. He explains that Isabella was not running from the black smoke but from this "devil". He adds that he saw the devil take Isabella but couldn't stop him. He claims that the devil betrayed him and has taken his body and his humanity. He deflects questions about the black smoke's murders and morality saying that if Richard wants to see his wife again he must kill this devil. The Man in Black gives Richard a knife.
All that remains of the statue is the foot after being struck by the Black Rock. Richard walks toward the base. As he approaches with knife drawn Jacob attacks and disarms him. Richard asks where his wife is. Jacob asks whether Richard met the Man in Black. Richard explains that the Man in Black said that the only way he could see his wife again was if he killed Jacob. Jacob says the person he saw was not his wife, that he is not dead and he is not in hell. Richard remains convinced that he is dead so Jacob drags him into the sea and submerges him until Richard says "I want to live!".
On the beach the two sit together. Jacob explains he is not the devil but that he brought The Black Rock to the Island. Richard asks why. Jacob uses a bottle of wine as a metaphor for the island. The wine is evil, malevolent, the bottle is containing it, because otherwise "it would spread." He explains that the cork represents the island, holding the darkness where it belongs. Jacob says that the Man in black believes everyone can be corrupted because it is in their nature to be bad and that he brings people here to prove the man in black wrong. When questioned on whether or not Jacob has brought people to the island in the past, and what happened to them, Jacob replies that he has but they are all dead. Jacob says he wants people to know the difference between right and wrong without being told. He then offers the job of representative or intermediary for Jacob to the people he brings. When Richard says that he wants his wife back, Jacob admits he cannot help, neither can he absolve him of his sins. However, he can help with Richard's third wish, to live forever and never die.
Richard returns to the Man in Black who realizes that Richard didn't kill Jacob. Richard gives him a white rock, a gift from Jacob. The Man in Black tells Richard that his offer of joining him will stand, he gives Richard the pendant and disappears. Richard buries his wife's pendant and crucifix and says goodbye to his love.
The Man in Black
After his meeting with Richard, The Man in Black is seated on a log overlooking a valley of trees, while tossing the white stone. Jacob joins him. When Jacob asks about the gift of the stone, the Man in Black tells Jacob not to gloat. Jacob asks whether The Man in Black sent Richard to kill him. The Man in Black says he did it because he wants to leave the Island and asks Jacob to let him go. Jacob tells the Man in Black that, as long as he is alive, that won't happen. The Man in Black says that is why he will kill Jacob, to which Jacob replies that someone will replace him. The Man in Black then says that he'll just kill them, too.
Jacob says that he'll see the Man in Black later and gives him the wine bottle he used to describe the Island to Richard as a gift to pass the time. Jacob leaves saying that he'll see him around. The Man in Black says to himself "sooner than you think" and then smashes the bottle.
Present day (2007)
At the beach camp
Jack, Hurley, Sun, Frank, Miles, Ben and Ilana are crowded around a fire, with Richard standing close by. Ilana and Sun explain that Sun, Jack and Hurley are candidates to replace Jacob. Frank asks what are they to do now but Ilana admits that she doesn't know. Not knowing what to do next, Ilana says that Richard knows and asks him. Richard laughs almost hysterically and says that he has no idea. He says that he was trying to kill himself. He says that everything Jacob has ever said was a lie. Jack asks for an explanation and Richard says he will reveal a secret that he has known a long time. He says that all of them are literally dead and that everything around them is not what it appears, that they are not on an island but they are in hell. Richard says it's time to stop listening to Jacob and to start listening to someone else and he takes a flaming torch and heads into the jungle.
Planning to go after him, Ilana loads her rifle and is interrupted by Jack, saying Richard has lost his mind, that if he cared about what Jacob said he wouldn't be talking about listening to someone else. Jack asks who Richard means to talk to. Sun explains that he means Locke. When Jack says Locke is dead Ben explains that it is not "exactly" Locke.
Jack goes up to Hurley who is a few feet away speaking in Spanish to someone. Jack interprets that he is speaking to Jacob and asks what is Jacob saying. Hurley says that it is not Jacob and that it has nothing to do with Jack. Hurley heads towards the Jungle.
Ben then confides to Ilana that going after Richard is useless as he doesn't know anything. She isn't sure, and Ben replies that he's known Richard since he was twelve. Frank asks if they've known each other since childhood but Ben explains that he has known him since "I was a kid" saying Richard looks the same as he did then. Frank realizes that Richard doesn't age, which Ben confirms and Frank asks, "Now, how the hell do you think that happened"?
In the jungle
Richard has been trekking all night and it is now the next day. Richard returns to the spot in a grassy clearing where he buried Isabella's crucifix at the base of a stone seat. He digs it up. Distraught he asks whether the Man in Black is listening to him and that he changed his mind, that he was wrong. He calls out asking whether the offer still stood.
Hurley walks out of the jungle and asks Richard what offer he is speaking of. Richard is amazed that Hurley is there and angrily pushes him away reminding Hurley that he doesn't know anything. Hurley asks him to calm down and as Richard starts to yell Hurley blurts out that it is Richard's wife, Isabella who has sent him. Richard reacts in disbelief. Hurley says that she wants to know why Richard buried the cross. He tells Richard that she is standing right next to him. Isabella says to Hurley that Richard doesn't believe him and Hurley explains that it sometimes takes a while. Richard slowly turns toward where Hurley is speaking. Although Richard can't see Isabella he now addresses her. Hurley suggests he close his eyes and he will tell Richard what she says. She wants to tell him it wasn't his fault for her death but that it was her time and that he's suffered enough. He tells her he misses her and would do anything to be with her again. Isabella says that they are already together. She kisses him and then is gone. Richard put the necklace and crucifix around his neck. Hurley smiles, and says that Richard "got it".
Hurley reveals that she also said there is something else that Richard must do. He tells him that he has to stop the Man in Black from leaving the island because if he doesn't "We all go to hell."
Some distance away, the Man in Black watches.