Attempting to use real-world examplars for D&D alignments makes for a rather poor fit. Real people just don't fall into such pigeonholes. We're too complex, and we don't have pantheons of pigeonhole-inhabiting deities directing our activities through unequivocal displays of their existence and power. Social norms direct our activities more than anything else, even if our inclinations toward selfish and altruistic behavior make us seem chaotic, lawful, good, and/or evil at times. This is true even with people who exhibit extremes of behavior.
Exempli gratia: Pol Pot, head of the notorious Khmer Rouge, led a hierarchical group; was he then lawful evil? His group was a revolutionary movement; was he then chaotic evil? He was almost certainly motivated to some degree by a personal desire for power; was he then neutral evil? Were nearly all of his followers of the same alignment as him? These really aren't answerable questions.
More to the point of the thread, as with any campaign, the key to an evil campaign is the players. Mature players who aren't asses in and out of the game can make just about anything work. I've been in evil campaigns that fell apart within a few games because one of the players used the alignment system as an excuse to be a jerk. I'm currently in a months-long drow campaign in which most of our characters are decidedly chaotic evil, and it's working extremely well with a great deal of fun being had by all. It's the social contract around the gaming table that allows that to happen.
Of course, for our group, we wouldn't have any problem with the rogue who gets arrested while acting as a courier. Our characters would be pretty darn unhappy, and there would be in-game consequences, but that wouldn't be a campaign-shattering event (if the message were that important, even MicMan's super-chaotic ADHD-ridden rogue should be able to keep his nose clean long enough to deliver it). Instead, we players would find it an amusing event. In all likelihood, we'd follow it up by having a grand time busting our foolish compatriot out of jail.