The battle between the couriers.

Based on OWB it's pretty clear that Ulysses' supports neither the NCR or the Legion, although Graham seemed to think he was a Legion assassin. My guess is that Ulysses disguises himself to blend in with the factions that don't like him just like the Courier does, thus explaining the different outfits. His true loyalties seem to lie with the Old World and he seems intent on finding a way to restore the world to its former glory, and somehow the Courier either stands in his way of doing that or could help him do that (it's not really clear which one it is yet, maybe both. )
 
Courier said:
Based on OWB it's pretty clear that Ulysses' supports neither the NCR or the Legion, although Graham seemed to think he was a Legion assassin. My guess is that Ulysses disguises himself to blend in with the factions that don't like him just like the Courier does, thus explaining the different outfits. His true loyalties seem to lie with the Old World and he seems intent on finding a way to restore the world to its former glory, and somehow the Courier either stands in his way of doing that or could help him do that (it's not really clear which one it is yet, maybe both. )
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The quote on his playing card states that he would lay his flag down over a 'nation he believes in'. One that you could convince/make him believe in?
 
I think that quote meant that he'll either bring back the Old World or die trying. The Old World America is clearly the nation he believes in, and he seems too smart to be able to convince him to trust either the NCR or the Legion.

Edit: His quote about America is in my sig.
 
That's in OWB, not on the playing card. Which came out before OWB.

edit: Possibility that you could convince him that America is dead? Hell, unless he just wants to kill you, he's probably going to listen to ya, considering you're important to him.
 
Yeah I know, that's his quote about him believing in pre-war America.

His quote from the card is, "The day I set my flag down it'll be over my body, or over a nation I believe in." The Old World America is that nation he believes in.

Here's my theory: Ulysses was originally a Legion Frumentarii disguised as an NCR soldier, until the company he was infiltrating reached a place known as the Divide and (I'll quote the wiki here)

Some terrible events happened there in the past, splitting the earth, destroying entire NCR companies and cutting off supply lines along California State Route 127, and State Route 88, which allowed Caesar's Legion more time to recover after their loss at the First Battle of Hoover Dam.
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It was here that he found some memory of the Old World hidden in the ruins and storms of the supposedly empty Divide. It was believed that all the NCR soldiers died at the Divide and survivors were only a legend (just like the Sierra Madre and the Big Empty and the survival of Joshua Graham were legends). Now here's what I think, Ulysses somehow survived what happened at the Divide and he learned some secret about the Old World (He did say he wanted to "Show the Courier what had happened there") and began to see the flaws in the Legion and became loyal to the Old World after he found a possible way to restore it.

He went searching for answers about something at the Big Empty eventually in his new quest to(House's securitron army possibly?).

Ulysses being an ex-frumentarii would explain why Graham thought he would come to assassinate him (Graham had lost contact with the Legion after the first battle of Hoover Dam, the same time the NCR company Ulysses was infiltrating had gone missing, thus explaining why he didn't know of Ulysses' new loyalties). Somehow the Courier is going to play into this and apparently has delivered a message to Ulysses before, either directly or indirectly, and Ulysses wants to show the Courier the glory of the Old World and how it can be restored. The Platinum Chip will play into this somehow (maybe Ulysses *wanted* Benny to get his hands on it? Possibly he somehow knew the Courier would survive? Maybe *he* was the one who placed Victor there in the first place long before House came along somehow knowing House would later use him to save your life?)


Edit: I'm going to re-post this all in my Lonesome road speculation thread.
 
Nah, I doubt they're going to give the Courier any sort of background. It's more likely the Courier is going to somehow be a part of all this unknowingly.
 
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