The solemnly proclaimed European Pillar of Social Rights provides a meaningful response to the process of building a deeper, fairer European Union in the aftermath of the crisis. The Juncker initiative generated positive momentum, with many relevant stakeholders expressing their support. The Pillar thus raised high expectations and interrogatives on the chances of an effective implementation of the social standards it lays down. This chapter aims to provide a critical assessment of the nature, scope, rationale, purpose, content, and effectiveness of the Pillar in light of its potential contribution to foster social fairness and competitiveness in the European Union. Delivering on the Pillar is part of an evolving process that raises significant challenges but also major opportunities. The Pillar complements and develops the EU’s social acquis and reinforces standards which may provide for a fairer and more socially balanced competitiveness. Progress has been made, but this potential needs to be fully harnessed by the Union and its Member States. On the road to Sibiu, further efforts are needed to build a sense of common purpose and to strengthen the social foundations of the EU.