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The aim of this chapter is to build on recent insights into the centrality of compassion in late medieval and early modern European culture by exploring the visual evidence for its influence on regulations concerning capital punishment and concern for the spiritual welfare of those condemned to death. The focus is on images of contemporary execution and of the Crucifixion of Christ on Calvary, the model for any Christian condemned to death. Images of contemporary execution reflect growing concerns and practices, such as the provision of comforters to minister to the condemned in the days leading up to their deaths, as well as the availability of confession and communion to facilitate a “good death.” Representations of the Crucifixion in the fifteenth and sixteenth centuries increasingly show Calvary as an execution site with gallows, wheels and crosses. Depictions of the Way of the Cross in the sixteenth century also begin to mirror the contemporary processions of criminals to their deaths, frequently showing the two thieves with their clerical comforters, whose role it was to show their charges Christian compassion in order to ensure their penitence and ultimate salvation by reflecting on Christ’s passion and the penitence of the good thief, Dismas.