Machiavelli has been conventionally understood as the proponent of extreme Machiavellism. He has been easily demonized as the advocate of tyranny pursuing private interests and power regardless of means and methods and of being unconditionally committed to evil, as well as a thinker who has completely disregarded morality and excluded this virtue from the realm of politics. By drawing upon a careful reading of his original writings, however, this article seeks to portray Machiavelli as a proponent of moderate Machiavellism rather than of the extreme variety. Although Machiavelli embraced the oft-mentioned Machiavellian elements of realpolitik, he also identified loopholes within Machiavellism. In particular, he was fully aware that Machiavellism—that is, the exercise of violence to achieve the purpose regardless of the means and method—may not bring the desired outcome and success. To be specific, this article proposes three reasons why Machiavelli himself must be interpreted as the advocate of moderate Machiavellism. First, Machiavelli called for the efficient use of violence as a means of rule. Violence should not be used consistently. The ruler must exercise violence at once and temporarily and must then obtain the public’s trust through proper dispensation. The inefficient or uncontrolled exercise of violence without the appropriateness in light of its consequences will inevitably lead to failure. Second, Machiavelli intended to constrain the use of violence and its evilness within the purpose and cause of the common good. He warned of negative consequences for the arbitrary and unrestricted use of violence. Finally, Machiavelli offered to use the violence in a timely manner. During the phase of founding a state when the concentration of power is highly required, immoral methods such as violence and deception can be tolerated. To govern the state afterwards, however, it is more important to have a form of governance that depends on a legal system or justice. In short, the main point of Machiavelli’s Machiavellism lies in his critique of the authorization of blind moralism and unconditional violence. Machiavelli himself was not a Machiavellian in the conventional sense.