This paper provides a history of the unique contribution made by Chilean lawyers to processes of political and social change during the past four decades. Chile is widely recognised as one of the classic cases of democratic transition after authoritarian rule: its experience was a forerunner for truth, justice, reparations and amnesty decisions in later transitions including the South African one. But the specific influence of members of the legal profession on Chilean transitional mechanisms has been understudied. The paper demonstrates that Chilean lawyers were pivotal in steering legal and political responses to the dictatorship, and they have played a key role in post-authoritarian transitional justice processes and in recent reform and rights debates. Chile’s long republican tradition since formal independence from Spain in 1810 includes a strong commitment to the notion of law, which helps explain why lawyers and legal framings were symbolically and practically important during and after authoritarian rule (1973-1990). Chile’s gradual and cautious approach to dismantling the legacies of dictatorship has relied heavily on law and legal arguments for both progressive and conservative purposes. As a case study, it can serve as a useful illustration of both the immediate benefits and the mid- to long-term drawbacks of a risk-averse transition that takes authoritarian legality as its starting point and avoids radical early innovation. The paper highlights how law was used in key periods since 1973, and assesses the prospects for democratic understandings of the rule of law to win out over authoritarian ones in the immediate future. Part one explains why law and legal culture are so important in this strongly legalistic society. The next three sections correlate with three main phases in Chile’s recent political history; a chronology of key events is provided at the end. Part two describes legal challenges created by 17 years of military dictatorship and the systematic human rights violations carried out by the Pinochet regime. Part three assesses the advantages and drawbacks of a strictly controlled transition that valued stability more highly than radical reform in building a new democracy. It also analyses how a domestic stalemate over questions related to dealing with the past was challenged by the 1998 Pinochet case, leading to renegotiation of Chile’s truth and justice balance. Part four assesses Chile’s transitional justice challenges nearly two and a half decades after the transition began. Criminal trials for past crimes have been reactivated, and there are moves to replace the country’s undemocratic constitution and modify its self-amnesty law. Longstanding promises to improve forward looking rights guarantees on a range of issues have started to be kept, now that part of the political right has softened its opposition to human rights language and ideas. A new generation of ‘cause lawyers’ or human rights lawyers seems to be emerging, though still in the minority in what remains a largely conservative legal profession.