The politics/administration dichotomy alludes at a disciplinary and practical separation between ends (politics) and means (administration). It has for a long time been considered as a hallmark of a rational government, and was at the basis of the ideas that composed the “evaluation package”, where it was complemented with the idea of the independence of evaluation from both poles. Starting from a criticism of the historical use of the dichotomy, this chapter enquires into the way in which evaluation has conceived its relationship with the dichotomy along the different waves of political innovations that followed the introduction of programs into policy-making: from Planning, Programming, Budgeting System (PPBS), to social action programs, to New Public Management (NPM), to governance, to evidence-based policy. In each wave, attention was focused on one or the other pole of the dichotomy, and mainstream evaluation was conceived as a support to the prevailing pole. Yet, each time instances of critical discussion put forward the need for collaboration between politics and administration, and proposed various ways in which evaluation could interact with both of them.