Freedom is the main pillar of the western social order. With freedom, comes competition. With competition, comes cheating. And cheating is not a zero-sum game. Each cheater extracts some benefit for himself, but inflicts a much greater harm on the society. As the complexity of the economic and political environment rise, the information asymmetries widen further between the producers and the consumers, between the politicians and the voters, and between the principals and their agents, making cheating easier and more beneficial than ever before. As cheating feeds on itself and spreads, concentrations of power in both the economic and the political systems emerge to promote their own interests, and Free Market Economy and Democracy start to fail to serve the society. Competition and Cheating explains why cheating, and consequently concentrations of power, have a natural tendency to emerge, spread, cooperate and strengthen within the economic and political systems, and what the society should do to escape this vortex that will eventually undermine its social order.