In "Pilot" it is learned that Robert is a criminal justice lawyer. He sustained injuries to his torso seemingly from debris in the crash. As the tail section of Flight 1213 was sinking, he and
Jason Bright assisted each other's escape before it submerged completely under the Atlantic Ocean. Upon reaching the shore, Winters was treated by Jason and
Dr. Trystan Dekker. After being led towards the treeline for shelter from the impending rain storm,
Nolan Gardner rounded up the group to move to structures located north of the crash site. Winters could be seen utilizing a steel pole he had recovered from the flight's remains for most of the time as a makeshift cane to keep him level due to the dizziness he was experiencing from significant blood loss.
As the group approached the runway,
Professor Noah Rose warned them that they were not alone on the island. Robert had suggested that they try to reason with the natives rather than killing them, Nolan then made an attempt to take charge of the situation. As Robert asks Nolan who had put him in charge, Nolan raises his firearm at him replying that the gun did. This likely set the tone for the group's attitude towards Nolan and his orders. In a further disagreement later on between Robert and Nolan, the group ends up splitting up and moving into two separate barracks.
