This paper clarifies issues of politics, morality and their relationship with a focus on the dirty hands problem. It elaborates this concept with reference to its most prominent proponent: MachiavelliMachiavelli, Niccolò. The MachiavelliMachiavelli, Niccolò program, as found in The Prince and the Discourses on the First Ten Books of Titus LiviusLivius, is outlined. Some important, but often neglected dimensions of this program such as the republic, the people, and the law are discussed. The MachiavelliMachiavelli, Niccolò program is confronted with Machiavelli’sMachiavelli, Niccolò philosophy of history which suggests that history repeats itself and therefore we can learn from past failures and successes. Obviously, cruelties are in the cartel of events that repeat themselves. There seems to be a direct path from cruelties to dirty hands which says that successful politics necessitates the violation of basic moral norms. In this chapter we meet TamerlaneTamerlane, Cesare BorgiaCesare Borgia, Richard IIIRichard III, Christopher MarloweMarlowe, Christopher, William ShakespeareShakespeare, William, Jean-Paul SartreSartre, Jean-Paul, and other specialists of the dirty-hand problem.