|This paper has the broad goal of inquiring into the role of empathy in contemporary interpretations of judgment as enlarged mentality. Specifically, it puts Hannah Arendt in dialogue with Karl Jaspers, her mentor and friend, on this question. While a disagreement (or even a conversation) on this issue never seemed to emerge between the two, I argue that they offer differing interpretations of enlarged mentality and specifically of the role of empathy within it. Arendt is skeptical of empathy and unfavorably contrasts it with imagination when it comes to their role in enlarged mentality. Jaspers, on the other hand, offers an understanding of empathy as fundamental for communication and understanding of the other. It is, for him, a dialectic process of bracketing and drawing from one’s own experience. While Hannah Arendt did consider Jaspers' thought as a bright example of enlarged mentality, I argue that she underplayed the role of empathy, and of idiosyncratic, non-necessarily cognitive elements in Jaspers' own formulation of it.