Ab Aeterno

In Tenerife in 1867, Richard tries to find a doctor to save his dying wife, Isabella. When the doctor demands payment, a scuffle breaks out and Richard kills the medic.

He races home to find that Isabella is dead and is promptly arrested for the doctor's murder. Instead of being hanged, Richard is put on a prison ship bound for the New World.

However, the ship hits a storm and – after hitting and destroying the four-toed statue – is stranded in the middle of the island. The ship's crew decide to kill all the prisoners to save resources, but Richard is saved by the Black Smoke.

After being visited by his dead wife, Richard is released from his chains by the Man in Black, aka Esau. Esau tells Richard that he will reunite him with Isabella if he does him a favour in return – kill Jacob.

Jacob talks Richard around. He explains that the island is like a cork that is the only thing keeping untold evil being unleashed on the world. Richard is granted eternal life in exchange for serving Jacob.

Esau vows that he will find a way of killing Jacob, who responds that a substitute will simply take his place as defender of the island.

Back in the 21st Century, Richard despairs for ever trusting Jacob and tries to summon Esau and join his side. However, Hurley makes him see sense after passing on a message from the dead Isabella.