I guess you're right if by "winning" you mean signing a deal and then having a criminal investigation into his behavior. I'd wager that no one won (customers lost, the publishers didn't make any more money and now Apple is stuck in a legal battle that all the counter parties have paid their way out of).
This is incorrect. The DOJ filed a civil lawsuit, not a criminal prosecution, against Apple.
The Feds are unlikely, IMHO, to win the case. Here's something that Greg Sandoval and I wrote at the time the lawsuit was announced, and I think it holds up well today:
http://news.cnet.com/8301-13578_3-57412861-38/