This paper explores the connections between party organizations, party attachments and legitimacy, and the ‘time component’. With both cross-party and cross-national perspectives, we address three questions: 1) Is the Party Strength Index (Webb and Keith, 2017) associated with party identification and popular legitimacy of political parties? 2) Do the democratic experience (years under democratic regime) and the ‘party age’ have an impact on party identification and legitimacy? 3) If they have any influence, does it occur directly or is it mediated by the party organizational strength? We consider three non-exclusive theoretical frameworks. The first sustains the relevance of democratic experience for the development of strong party organizations and party linkages (Aldrich, 1995). The second emphasizes the relationship between party age (which is sometimes seen as a proxy for party institutionalization) and party organizational strength, which produces positive impacts on the electorate (Dix, 1994; Tavits, 2013). Finally, the differences may be connected to the party genetic model: parties created during non-democratic (or unstable) regimes tend to cultivate stronger ties with the electorate (van Biezen, 2003). We rely on the largest cross-national dataset to date on party organizations, the Political Party Database Project (round 1 data). Following the tradition of ‘most different’ approach in comparative analysis of party organizations (Janda, 1980), we add to the dataset original data from three presidential Latin American countries. Overall, we employ a database with 142 parties in 22 countries, covering third-wave democracies, post-communist countries and advanced democracies. Other kinds of data come from the Word Values Survey and the European Social Survey; the project Members and Activists of Political Parties (party origins and party year’s foundation, van Haute and Paulis, 2015); and the Polity IV.