This chapter examines the role and impact of political connections among non-financial listed companies in Italy between 1987 and 2006, a period marked by profound institutional and political transformation. It explores how shifts from the First to the Second Republic, the rise of new political actors, and widespread privatization influenced the relationship between business and politics. Leveraging a unique dataset that matches politicians with corporate board members and shareholders, the study identifies different types of political ties—through top officers, large shareholders, or both—and evaluates their influence on corporate leverage, efficiency, profitability, and market power. The findings reveal that politically connected firms tend to show lower accounting performance and efficiency, yet benefit from significantly greater market power, particularly when the connection is established via ownership. Contrary to international literature, connected Italian firms show lower access to credit, suggesting a distinctive institutional dynamic. This chapter offers crucial insights into the Italian model of political capitalism, providing a nuanced understanding of how entrenched relationships and historical legacies shape corporate behavior and governance in a developed economy with persistent institutional weaknesses.