This study identifies three drivers of the break in the majoritarian path to which electoral reforms seemed to be leading the Italian political system since 1993. The first is the unconventional political landscape, with the rise of the Five Star Movement and significant fragmentation of parties. The second is the “original sin” of the Italicum, designed under the assumption that the Senate reform would be successful. The third driver is the groundbreaking intervention of the judiciary, called repeatedly into question in order to assess the constitutionality of the Electoral Law in a context characterized by the progressive decline of Italian politics. The article will focus on drivers two and three and will proceed as follows. The first section will draw a general picture of the changes that have occurred in Italian electoral law after 1993, underlying the common aim shared by all recent electoral law interventions: to foster the affirmation and consolidation of a bipolar pattern. The second section will focus on the landmark decision of the Italian Constitutional Court (ICC), Decision No. 1/2014, which struck down Law No. 270 of December 21, 2005 (Electoral law for the Chamber of Deputies and the Senate of the Republic). This decision paved the way for judicial intervention in a sphere typically left to the mediation of different political interests and gave the legislature the way forward which led to the Italicum. The third section will deal with the Italicum, addressing its genesis, its primary features, and the declaration of unconstitutionality by ICC Decision No. 35/2017. Finally, the fourth section will address the currently open issues and the need for a legislative intervention which could determine whether the Italian political system will follow the majoritarian trend in the name of government stability, or if it will be hostage to both the political conflicts and the institutional flaws of super-perfect bicameralism.