Inside Man/YMMV


 * Magnificent Bastard -- Dalton Russel (Clive Owen). He's literally planned for everything, has contingencies in place, expertly manipulates both the situation and the people involved, and . Madeleine White is heavily implied to be one as well. When the mayor of NYC calls her a "magnificent cunt", she answers "Thank you". While she seems to be playing for the bad guys, in the end it's clear she does her own thing. The biggest problem with classifying her may well be that we don't see enough of her, and she never really demonstrates any Chessmaster ability.
 * Nice Job Breaking It Hero: Dalton admits that he pulled the heist out of greed, and assuages his conscience by stealing from (and ensuring the downfall of) a man who collaborated with the Nazis. While it is a very valid point that such evil deeds should be brought to light, what is most likely afterwards is that Case, a man who has dedicated the majority of his life to helping mankind, will simply be replaced by a normal banker, one who cares only about his own profit. All of the possible charities that Case would have continued to help out, are left to rot because a thief thought he found the perfect Asshole Victim.