The scholarship on political careers and recruitment has increasingly focused on the conditions that foster the emergence of new political elites. However, top politicians in democratic regimes often share socio-economic backgrounds and occupy similar political positions before entering office. Career patterns in politics are relatively stable and tend to reproduce themselves over time; this leads to the persistence of core background traits among the members of the political elite. The lack of profile renewal seems at odds with the claim of democratic theory, which asserts that democratic competition is open, inclusive, and expansive. Despite its relevance, the causal mechanisms behind career patterns’ stability among political elites have received little systematic attention. This article contributes to fill the gap, by focusing on democratic chief executives. First, it clarifies the core concepts for the study of political elites and careers. Second, it proposes an understanding of the formation and stability of chief executives’ career patterns as functions of path-dependent institutional effects. Third, the work uses this theory to investigate persistence and renewal of the background characteristics of all US presidents, from George Washington (1789) to Joe Biden (2021). The analysis contributes to the literature on elite stability, circulation, and renewal in democracy.