Article 20 TFEU establishes the citizenship of the European Union. A core element of EU citizenship is the right of all EU nationals to move and reside freely within the territory of EU Member States. The free movement of EU nationals brings with it the issue of their access to social benefits. The interaction between the two notions comes into play when a national of one Member State applies for or receives social benefits in a Member State other than that of his/her nationality. The Court of Justice of the European Union (CJEU), which plays an important role in interpreting EU law provisions, has addressed the abovementioned issues in a number of judgments. However, the Court’s jurisprudence in this regard has changed throughout time from an EU citizen-friendly approach to a more Member State-friendly one, albeit with some recent changes of mind. This evolution has been taking place not in an isolated legal vacuum but rather in a specific socio-political context, which has been shaped by several factors. This thesis analyses the evolution of CJEU case law on free movement of persons and social benefits with the aim of contextualising its development. The thesis then examines several institutional, social and political dynamics, which provided the background for the developments in the Court’s jurisprudence. Particularly, the thesis suggests that the 2004 enlargement, the increase of intra-EU migration and the rise of Eurosceptic populism - most evident in the Brexit process - were the background of the CJEU jurisprudence and may play a role in explaining its evolving approach. By answering its research question through an interdisciplinary lens, employing the ‘law in context’ approach, this thesis argues that the Court’s case law developed in its socio-political context, and uses the example of the UK as a case study to support this argument.