This article aims to improve our understanding of criminal legitimacy-building phenomena by comparing extortion practices performed by criminal groups in Sicily, Italy and Michoacán, Mexico. It is argued that these extortion practices, known as pizzo in Italy and as cobro de piso in Mexico, do not only have a practical dimension but also a symbolic one. On the one hand, the practice of extortion produces incomes for the criminal group. On the other hand, extortion works as an authority claim and is linked to the political legitimacy discourse of the criminal group. This article explores this second, symbolic dimension of the practice of extortion by comparing the results of qualitative field research in Sicily and Michoacán. It is argued that extortion does not only work as a form of parallel taxing, but also shapes the contact and creates a closer relationship with the local population. Pizzo and piso then work as power-reaffirmation devices by configuring a particular political display related to the political legitimacy interest of the criminal group that engages in extortion practices.