The increase in income and wealth inequality in Italy is well documented, but less attention has been devoted to its association with social and political outcomes. This article investigates the association between inequality and several variables on socio-economic conditions with the evolution of Italian politics over the 1994–2018 period. Voting in Italy’s regions for the centre-left and centre-right coalitions—with a focus on the Lega—is examined in seven rounds of general elections, before and after the 2008 crisis, which emerges as a key divide in these relationships. The centre-left vote is higher in the regions with an increase in mean wealth and employment rates and shows a reversal after 2008 in the support of part time employees. The centre-right vote is associated with impoverished middle classes and an increase in disparities of Southern regions. The associations shown by Lega voting are distinct from those of other centre-right forces. While political and cultural factors are important to understand political changes, our findings show that a more unequal and distressed society is clearly associated with changes in electoral behaviour.