Smart Cities are conceived as strategic models to confront the wicked problems that exist in urban contexts. The research literature, however, reflects a lack of consensus on the elements that make a city "smart." While some authors focus on technological aspects, others consider human factors as principal targets of the cities' initiatives. Aiming to shed light on this discrepancy and understand what makes a city smarter, in this paper, we analyze a large number of real case studies implemented in major European Smart Cities. From our analysis, we first characterize and categorize the cities according to theoretical Smart City models proposed in the literature. Based on the cities' characteristics and categories, we then compare them according to external variables, such as their positions in worldwide Smart City rankings, and their administrative contexts.1