The author begins the chapter with an example of the feeling of collective guilt of an Anglo-Saxon teacher concerning the removal of Cherokee from their ancestral homeland in what is now considered the United States. The author questions whether the teacher is empathetically engaged with the past. He states that there are two types of empathy, one in which we attempt to understand and make sense of why people in the past did what they did by attempting to get inside their heads and hearts and, secondly, a feeling of emotional empathy in response to a tragedy that is difficult to bear. Historical empathy is not simply placing oneself in another’s shoes, rather it requires a high level of thinking where the beliefs, values and goals of people of the past are entertained and worked with in order to explain and understand what was done in the past. There are five levels of historical empathy discussed in the chapter. The author continues with a discussion of the problems of historical empathy: that it requires a high level of self-examination regarding our experiences and assumptions, that there is a lack of well-honed tools and unbroken evidence to truly accomplish historical empathy, and the necessity of removing our positionalities in order to avoid being a presentist. He also discusses the empathetic historian as ‘psyche-snatcher’, time-traveler and necromancer. The author concludes with a discussion of how to move from empathy to historical contextualization and finally to self-understanding.