18 People Who Spectacularly Gamed The System

Cheaters never prosper, or so they say. While some people can get away with it and accomplish some things like becoming President of the United States of America, most of us will eventually get caught and punished if we cheat in anything. And they'd be right to do it. Cheaters are not cool and should pay for their behavior.

People who find loopholes, on the other hand are heroes. They not only played by the rules, but outsmarted the rules. There some sort of roguish hero quality to those who studied the game of their industry or life in general and found ways to get ahead by bending the rules or working around the margins. It sounds more romantic than it is, but it's great so see someone get some additional free miles from the price gouging airline industry.

Read on about these smarter-than-the-average-consumer heroes who gamed the system and won big: