The Courier, from some reason, built up Hopeville, a place that Ulysses called home. However, the Courier brought a package from the NCR who salvaged it from the ruins of Navarro. The package was brought to Hopeville and turned out that it was a detonator/beacon. The Courier didn't set it off (at least it isn't assumed that he did)but he delivered it and afterwards, it signaled to the hundreds of nukes in the area.
They detonated, destroying Hopeville and the surrounding area. Ulysses survived because of the symbol of America on his back (Medical Robots).
His meaning to the Courier through a two part meaning.
Part One is that he tells the Courier that one man can change the world, for better or for worse. This is shown throughout the main game as the Courier is the driving force of one of the armies. Not to mention Ulysses saw this first hand with the Courier's delivery of the detonator.
Part Two is criticism of the factions the Courier sides with, because of all their faults.
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NCR - It's part of old world values that caused the bombs to drop. Not to mention that the fly their flag of democracy so broadly and openly without knowing its true meaning. Especially since the NCR is ripe with political strife amongst their own politicians.
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House - Ulysses also hates Mr. House as much as NCR. He sees it as reawakening a dead value that isn't really needed in this new wasteland. Especially the fact that Mr. House is stuck in the past and resurrecting the Old World more blatantly than the NCR ever did.
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Caesar's Legion - Ulysses shows less hate but still points out failures. That if Caesar dies and there's no heir, they'll crumble. But a massive eye opener here is the idea of an Empire. Although it's flawed, it makes sense. When the Legion attacks the NCR and takes it over and have nowhere else to expand to, they'll turn on themselves. While there's a vast eastern area to conquer, it still makes sense. Once Caesar expands to its Legion's limits, they'll kill themselves.
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Independent - Never done independent. My current playthrough is going indie so