The beginning and end of this chapter mirror each other in that one Akatsuki member is commenting on how their partner seems to be crying. Itachi is reflecting on his brother Sasuke (and how he was nearly killed) and Pein is thinking about his upcoming battle with Naruto. Given that Pein looks a lot like Naruto, I think we're meant to believe that there is a connection between Naruto and Pein. Maybe they are also brothers, which would suck for Pein because since he has never lost a fight, he would have to kill his brother.
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