In the 2004 timeline, Desmond is Widmore’s right-hand man, living a materialistically successful but emotionally detached life.
: Tasked with retrieving a drug-addled Charlie Pace for a concert, Desmond experiences a near-death event when Charlie drives their car into the ocean. Watch Lost S06E11
: While submerged, Desmond sees the iconic "NOT PENNY'S BOAT" message on Charlie's hand from a previous timeline. This vision, later reinforced during an MRI scan, awakens memories of his life with Penelope Widmore. In the 2004 timeline, Desmond is Widmore’s right-hand