I was thinking that as a possibility as well..

__________________
Please don't give up, Des. Because all we really need to survive is one person who truly loves us. And you have her. I will wait for
you. Always. I love you, Pen

DESMOND: I love you, Penny. I've always loved you. I'm so sorry. I love you!
PENNY: I love you too.
DESMOND: I don't know where I am, but--
PENNY: I'll find you, Des--
DESMOND: --I promise--
PENNY: --no matter what--
DESMOND: --I'll come back to you--
PENNY: --I won't give up--
BOTH: I promise. I love you.

Really, even today? You can shoot your fellow american in the back if he is running away from everyone? Figures... Crusaders in camo

__________________
Ted Striker: My orders came through. My squadron ships out tomorrow. We're bombing the storage depots at Daiquiri at 1800 hours. We're coming in from the north, below their radar.

Elaine Dickinson: When will you be back?

Ted Striker: I can't tell you that. It's classified.

no, you cannot shoot deserters in the back.
But, desertion during combat is a capital offense with execution as a possibility.
Only after a courtmartial, though, can you be shot for it. In the front, though, not in the back. Well, they might make an exception if it was your last request.

what you got against the US Army or the British Army?

what you got against the US Army or the British Army?

Jesus, i could write a book on that...


Well its no so much the people who are in the army/marines/navy/air force that i despise its more the people that make their decisions that don’t have to see battle - playing chess with people lives over power and wealth that should all be taken to an old concentration camp and burn together. Just remember that someone will always profit from a war, and it is usually people who have facilitated that war and found out how to reap the benefits...

__________________
Ted Striker: My orders came through. My squadron ships out tomorrow. We're bombing the storage depots at Daiquiri at 1800 hours. We're coming in from the north, below their radar.

Elaine Dickinson: When will you be back?

Ted Striker: I can't tell you that. It's classified.

then your beef is not with those "crusaders in camo", but with governments.
It just seemed derogatory to call soldiers that in a sarcastic way.
no offense taken, just wondering what you mean.

Another interesting bit on Des that I remember. When he gets released from military prison, who is waiting for him outside? None other than Mr. Widmore. That is when he gives Des $ and tells him to stay away from Pen. After that he gets the boat from Libby, enters the race and ends up on the island.

__________________
"See ya in another life, brotha"

DesmondsBrutha, it was when I saw him meet Des outside of the prison that I just knew that he put des on the island via Libby.

Good theory...
For what purpose would Widmore put Des there?
And was Libby's island time purposeful or accidental?

__________________
"See ya in another life, brotha"

Actually, I've believed Libby was Dharma or whidmore or whatever, ever since around the time she was killed. the Desmond, Whidmore, and Libby thing congealed for me back then with her giving des the boat.

I had originally thought about him putting des there to make sure he never sees penny again..... but later began thinking that whidmore had des there as a way of finding and getting control of the island.

I think you are pretty close to accurate on the timeline....we know he did not know Penny when he left the Monastary, so he had to have been there first. Plus, after he broke up with that other girl he was engaged to, he left and went to monastary.