This chapter focuses on the 1970s and 1980s during which MacCormick confronted and developed his political philosophy, with a special focus on the essays that were collected in Legal Right and Social Democracy (1982). This includes how MacCormick crafted a middle space between liberalism and socialism, which he called ‘social democracy’. It also includes MacCormick’s work, in this period, on obligations and rights. This chapter discusses the sense in which this conceptual work can be read with character, e.g., how his concepts of obligation and rights relate to his basic commitment to respect for persons (including a concern for the temporally-extended quality of relations between persons). It also places this philosophical work in the context of the politics of the period, e.g., the SNP’s own eventual endorsement of a social democratic platform, and it discusses how MacCormick’s political interventions in this period (e.g., his actions with respect to the’79 Group) can also be understood as expressions and negotiations of his character. Overall, the chapter explores how MacCormick’s character is expressed and negotiated in his role as a jurist, making law as morally intelligible as he could, seeking to limit executive power legally, and also diffusing and decentralising power as much as possible.