This chapter explores the emergence of trade unions in Sri Lanka and their engagement with representative and movement politics. The choices which trade unions face under neo-liberal globalisation directly relate to specific historical trajectories shaped by anti-colonial struggles and the evolving “self-governing” nation-state strategies. Representative politics refers to the realm of representative governance institutions involving citizenship, where political party formations shape parliamentary and electoral processes. Movement politics concerns the realm of social movements and contentious collective action, which elaborates the roles of citizens as well as of civil society actors. This chapter will attempt to explain the ways in which union relations with political parties emerged and the moments of compromises that restrained their role as civil society actors.