I too am stuck on a weird island run by a suspicious leader; except the weather isn't as nice and the others wear Burberry. I don't have a dark enough backstory to be in Lost. However, If I were a character, it would probably go something like this...

On The IslandEdit

Rob woke up in the jungle, after finding his phone was useless he discovered the crash site on the beach.

Rob found several small bottles of in-flight alcoholic drinks which were soon exhausted, forcing him to quit cold turkey(The Moth). Later he was one of the first to investigate the computer in The Swan

On Day 33, he witnessed Walt setting fire to the raft, but kept it secret out of his friendship with him. (...In Translation)

On Day 49 Rob establishes contact with Walt via The Swan's computer and first learns of the Decoy Village (The 23rd Psalm)

On Day 62 Bea Klugh, warns Michael to keep Rob quiet about his communications with Walt(Three Minutes).

In the days following Jack, Kate and Swayer's capture Rob helped to organise the survivors in the absence of many of the A Team. He helped to organise treks to recover food left by the implosion of the hatch but insisted that the kidnapped would come back.