Contrasting security to privacy is one of the well-known manifestation areas of the popular approach according to which competing values and demands in a democratic society, as well as the fundamental rights reflecting them, can only be realized at the expense of each other, by creating a balanced result in a virtual zero-sum game. This chapter presents how democratic legal systems handle conflicting fundamental rights and legitimate interests, and show how the judicial practice seemingly corroborates the illusion of inevitableness of the trade-off. From among the two main methodologies developed in democratic rule-of-law traditions, it analyses the European one, the test of proportionality in detail, and shows how methodological rigour in using the test can help superseding the trade-off model within the legal domain. The chapter offers suggestions that, if implemented, will make it possible to move away from the security–privacy trade-off both in judicial practice and decision-making environments.