Jacob visits a bandaged Ilana in a hospital and tells her she has six people to protect – the remaining candidates. Ilana admits to the candidates that she does not know what to do next, but Ricardus (Richard) does. Richard laughs this off, and tells Jack that they are all dead and are in Hell. He says that he is no longer listening to Jacob, and will start to listen to someone else – DeathLocke – before stalking off alone into the jungle.
 
Canary Islands - 1867. Richard Alpert, looking the same age as he does more than a century later on the island, tends to his beloved, Isabella, who is dying.  He rides through the night to buy medicine from a doctor. He tries to pay for the medicine with Isabella’s gold cross and all the money they have, but the doctor tells him it is not enough. A fight ensues and Richard accidentally kills the doctor. He makes off with the medicine, but when he returns home, Isabella has died. He is quickly arrested for the doctor’s murder. In jail, Richard begs for God’s forgiveness, but the priest tells him that he is going to hell and is to be hanged in the morning. However, on the way to the gallows, his freedom is bought by a Mr. Whitfield for Magnus Hanso, captain of the Black Rock. Richard is taken to the ship and chained below deck, but in a storm the ship crashes into the island, colliding with the giant Egyptian statue. Mr. Whitfield quickly dispatches with the other slaves, fearing that their limited supplies will lead to mutiny, but before he can kill Richard, the Smoke Monster arrives and kills him. The Smoke Monster stares down Richard, who closes his eyes and prays. When he opens his eyes, the smoke is gone.
 
Isabella visits Richard, still chained in the hull of the ship. She tells him that they are both dead and have to flee before the devil returns. The Black Smoke returns and takes Isabella away from Richard again. Eventually, the Man in Black appears to Richard, bringing him water and calling himself a friend. He tells Richard that he is in hell and that there is only one way to escape: to kill the devil. He gives Richard the same ceremonial dagger and instructions that DAGON gave Sayid – stab the devil before he can say a word. Richard is told he must do this if he ever wants to see Isabella again. Richard travels to the foot of the statue, where he is attacked and disarmed by an incensed Jacob. When Jacob realizes that Richard had spoken to the Man in Black, he calms down and shows Richard that he is not dead by trying to drown him. Jacob explains that the island serves as a plug, keeping evil from spreading. He reveals that he brings people to the island to prove that they are capable of being good. He offers Richard a job: serving as his representative to the people he brings to the island. In return, he grants Richard everlasting life. Richard returns to the Man in Black, who tells him that his offer will still stand if Richard ever changes his mind.
 
In the present, Richard digs up Isabella’s cross, which he had buried all those years ago. He shouts into the jungle that he has changed his mind, but instead of DeathLocke appearing, Hurley arrives. Hurley channels Isabella and through him, she tells Richard that it was not his fault that she died, and that they will always be together. She warns Hurley to tell Richard that he must stop the Man in Black; if he doesn’t, they all go to hell. DeathLocke looks on from afar.
 
The episode ends by returning to the 1800s. Jacob visits with the Man in Black, who tells him that he will keep trying to kill him until he lets him leave the island. Jacob gives the Man in Black a bottle of wine, which he smashes on the rock.