S6E9 · Ab Aeterno

In 1867, Richard accidentally kills a corrupt doctor while trying to get medicine for his dying wife Isabella. He is sold into slavery on the Black Rock, which crashes into the Tawaret statue. The Man in Black kills the slavers and uses visions of Isabella to convince Richard that he is in Hell. He tells him that Jacob is Satan and orders Richard to kill him, but Jacob disarms Richard and explains that the island keeps the Man in Black from destroying the world. Fearing Hell for killing the doctor, Richard asks Jacob to make him immortal in exchange for being his representative. In 2007, Richard renounces Jacob and decides to join the Man in Black, only for Hurley to speak for Isabella's ghost and beg him to save them, restoring his faith.