This chapter sets out the development of Social Europe, focusing on the defining role of politics in the process and tracing its portrayal in the pertinent literature. Social Europe has been through a tremulous journey of numerous ups and downs throughout the years, where hopes of a breakthrough were repeatedly dashed by a variety of factors, often linked to politics. The analysis identifies four such factors as being instrumental to Social Europe’s uneven trajectory: first, the reliance on new modes of governance; second, the centrality of the Member States’ authority and its influence on their interaction with the EU; third, the allegedly inherently economic character of the European project; and fourth, the 2008 economic and financial crisis. All highlight the influence of politics in advancing – or rather, stalling – the realisation of Social Europe. The recent initiatives centred around the European Pillar of Social Rights show a stronger commitment to Social Europe. Nonetheless, the end result of this commitment continues to gravitate between success and failure, depending on the manner in which politics is assimilated therein. In a journey of self-reflection, Social Europe could contemplate its tainted past and reinvent the contribution of politics as a lesson learned, or it could simply remain Laodicean, trapped in a vicious circle of political path-dependence.