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Fallen Hero
I'm pretty sure Jack keeps telling Oz that nothing he has is real not only to try and keep his spirit broken, but because that's how Jack himself feels.
No matter what he had, no matter how far he advanced or the friends he made or anything, he still had nothing - it was all fake. He looked like he was there, but he never really was.
And then the one thing he thought he did have, Lacie, he found out wasn't really his either. So even though he was already someone who had nothing, he still managed to lose everything.
His words to Oz are words to himself.