Crime is a deviation from social norms, causing societal disorder and economic loss. Many researchers have pointed out that economic factors constitute a critical element in the decision on committing a crime. The police are supposed to control crimes. To be sure, the law is enforced by human beings, subject to similar potential deviation. Consequently, the deviant behaviors of law enforcement must also be addressed. This paper explores the general issue of monitoring, in addition to enforcement. Similar monitoring concerns exist in the political arena and the business environment. A simple model based on monitoring concerns is proposed and used to delineate a possible evolutionary path of the political system. Politicians and representatives can be considered as guards hired by the people to protect the fruits of their hard work. However, worries about the guards’ misdemeanor may necessitate further deployment. Under rational guard hiring, the negative relationship between the effectiveness and the number of guards may shed light on the evolution of the political system. The result is applied to analyze a proposal on cutting the size of the legislature in Taiwan.