What is disintermediation? In wider terms, it indicates the absence of a median entity between two subjects. As is known, it was a term born in the economic-financial sector, which then spread to different areas of social life. This variety of uses has made it ambiguous, an ambiguity that can develop on two levels. The first is almost inevitable because it is the consequence of its varied use. By disintermediation we can mean, for example, the absence of mediators during an economic negotiation, the possibility of buying a plane ticket without travel agency costs, or the dynamic that is created between society and institutions with the use of Internet in the political arena. From this point of view, the word is ambiguous because it is overly generic. The second level of ambiguity relates to the relationship between disintermediation and democracy because, on the one hand, it allows us to accept the requests of citizens who want a more direct and transparent relationship with the political elites, and, on the other, it risks making some elements of representative government even more brittle, especially by undermining their legitimacy. As the title suggests, this book explores this second level of disintermediation ambiguity, offering a series of contributions that, using different approaches, highlight also the more dangerous aspects that risk even undermining some keystones of liberal-representative democracy.