Throughout the world, democratic countries, whether old, new, or in transition, are facing innovations in communications and information technology. Especially within developed economies, the challenge toward e-democracy through the digital transformation of democratic institutions has become increasingly evident. With the identification of the notion of the “middleman paradox,” recent research findings have added a new dimension to existing theories on the hesitant evolution of e-democracy, which clearly identifies politicians as an inhibiting factor. Consequently, the research in this chapter attempts to explore further this newly discovered phenomenon by presenting theoretical and empirical evidence. The findings of a multiple case study carried out in all 25 EU member countries, based on an adopted exploratory research design are presented. These findings give more detailed insights on the nature of the middleman paradox and on the ambiguous role of politicians in the further evolution of e-democracy.