Fan theory - None of the stuff from the past actually happened ...
None of the stuff he talked about when he was sitting on the bench actually happened - at least not to him directly.
Think about it. Here's a guy who won the medal of honor, international ping pong championship, cross-country runner, multi-millionaire, etc, etc, etc yet no one on the bench that he talks to recognizes him (or really believes him)? Also, once we're in the present time, he doesn't do anything extraordinary anymore, nor does he do anything to show his vast wealth!
As for the pictures that Jenny shows him in magazines and newspapers, I'm thinking his friends and family printed those things out to support his imagination, or whatever that is, because they see that it brings him a lot of happiness to talk about.
Maybe this was the idea behind the movie/book the whole time, but I haven't read anything anywhere to indicate that this is the case.
Thoughts?