At the end of the last episode, the Losties discover a sailboat floating around just off the island. Jack, Sayid, and a few others swim to find out who is occupying this mysterious boat. And it’s none other than everyone’s favorite adorable Scottish man, Desmond. And in this episode, we get a little peek into his past.
First, we find out that Desmond served time in prison and was dishonorably discharged from the Royal Scottish Army. Upon his release, he meets up with a rich-looking white-haired man who turns out to be the father of Desmond’s lost love, Penelope. The man offers Desmond a large sum of money to stay away from his daughter.
Desmond doesn’t accept the money, and instead decides to take on Penelope’s father, Charles Widmore in a sailing race around the world. While he is training for this race, he runs into a familiar face at a coffee shop – Libby, who donates her late husband’s boat to Desmond.
Then we get to see Desmond on his sailing expedition, and where he gets into some rough waters that eventually lead to him crashing on the island. But all of this happens after he meets with Penny for one last time and tells her that they will be together when he returns.
Back on the island, Sayid finds a use for that boat and a way to gain an advantage over Michael and the Others. He decides to sail the boat around the island to get there before Jack and the rest of them. He plans to start a fire with some leaves to make a large cloud of black smoke so that Jack will know where he is. He warns Jack not to tell the rest of them though, for risk of Michael finding out.
So Sayid asks Jin and Sun to accompany him on his sailing expedition. On the way, they run into something very peculiar – a statue (or what’s left of it) of a foot with only four toes.
But Jack, Kate, Sawyer, Hurley and Michael are running into problems of their own. After discovering that they are being followed by two of the Others, Jack lets it slip that Michael has been turned. Tensions are high, especially when Hurley finds out that it was Michael, not Ben, who killed Ana Lucia and Libby, but they keep moving toward their destination and wait for Sayid’s signal fire.
On the other side of the island, Locke is getting very frustrated with Eko’s determination to press the button. He recruits Desmond and together they put together a plan to get him to stop. Desmond activates the blast doors, locking Eko on the side opposite the button. Then John and Desmond wait.
While they wait, Desmond remembers the day that flight 815 crashed on the island. He realizes that this is the day he reached the button just a second too late. Upon this realization, he decides that the button needs to be pushed, but John smashes the computer. Desmond then remembers the “fail safe” that his predecessor in the Dharma Initiative, Calvin, once told him about. Not knowing what will happen, Desmond takes a key into a little crawl space.
The countdown goes past zero, all the weird symbols show up, the ground starts shaking and all the metal in the hatch starts flying. John realizes he was wrong, but it’s up to Desmond to save them now. He says a prayer, turns the key, and everything goes white.
On the opposite end of the island, Jack, Kate, Sawyer and Hurley have been captured by the Others. They realize that their former captive, Ben, is their leader. Ben lets Michael and Walt go, and he gives them a boat.
The Others let Hurley go, and tell him that his job is to return to camp and tell the rest of the survivors not to go looking for Jack, Kate and Sawyer, who will be leaving with the Others.
At the very end of the episode, two men are sitting in what looks to be a small boat. A meter or alarm of some kind starts going off and the men look shocked. One of them gets on the phone …with Penny Widmore. He says that they think they have found “it.”