The pardon is an act of mercy, tied to the divine right of kings. Why did New York retain this mode of discretionary justice after the Revolution? And how did the advent of the penitentiary and the introduction of parole transform governors’ use of their prerogative? This book answers these questions by mining previously unexplored evidence held in official pardon registers, clemency case files, reports of prisoner aid associations, and parole hearing records. This is the first work of history to analyze mercy and parole through the same lens, as related but distinct forms of discretionary decision making. It draws on governors’ public papers and private correspondence to probe their approach to clemency, and it uses qualitative and quantitative methods to profile petitions for mercy, highlighting controversial cases that stirred public debate. Political pressure to render the use of discretion more certain and less personal grew stronger over the nineteenth century, peaking during state constitutional conventions, and it reached its height in the Progressive Era. Yet, New York’s legislators left the power to pardon in the governor’s hands, where it remains today. Unlike previous works that describe parole as the successor to the pardon, this book argues that reliance upon and faith in discretion has proven remarkably resilient, even in the state that led the world toward penal modernity.