National and international lawyers are ubiquitous in transitional political negotiations. However, their role in advancing or stalling negotiations, or in advocating or resisting progressive change, is generally carried out behind closed doors. This chapter explores when and how lawyers living and working within repressive, conflicted, and transitional states influence the content of transitional political agreements. It draws on twenty-five interviews with lawyers who participated directly in negotiations and other informed commentators in our case study sites. Combining this empirical data with literature on lawyers as negotiators, the sociology of the legal profession, and critical international legal theory, the chapter explores the factors that shape relationships between lawyers and the political leadership in negotiations. The chapter further critically analyses the extent to which lawyers’ negotiating styles and legal skills can advance or inhibit the reaching of an agreement. The final section explores the discretion and capacity of lawyer-negotiators for legal imagination in crafting transitional futures. We find that lawyer-negotiations often have to grapple with reconciling their role as legal technicians with the ethical and political challenges of advising on law’s content at times when the law itself is indeterminate or subject to negotiation.