LostArk said:
They should have made a scene explaining what happened to him between Indy 4 and Lost
Well, Charles Widmore was a military man... Hence the adoration of McCutcheon and his questioning as to whether or not Desmond had been enlisted. Then, between the 50's and the present, he did not age a day...
You see, after he had his run-in with Indiana Jones, he decided to change his name from Ross and go looking for the Island. The very same aura that surrounds Richard Alpert surrounds Widmore too. It was then that Widmore leaves the island and begins his multi-billion dollar corporation that one day sponsors a solo race around the world.