There has been a great deal of international debate about introducing historical empathy as the focus in teaching history. However, as it is, the contents of the concept have been included in the curricula in many countries. Nevertheless, practising stepping into the shoes of a person from a previous era is still in its infancy in schools in many locations – Finland included. This article discusses Finnish class teacher students' understanding of historical empathy. The article is based on a study where 360 class teacher students played a game simulating the Cuban Missile Crisis. Their task was to assume the roles of the superpower leaders and make decisions on the basis of these roles. The simulation showed that a majority of the student teachers are able to attain a level of contextual historical empathy. They were able to empathize with the historical context in question and make such decisions that would have been possible for the historical actors. Some of the playing groups on the other hand, referred to their current knowledge and attitudes, which, according to Ashby and Lee's empathy classification, shows lower-level empathy. The study corroborates previous research results concerning great discrepancies in the understanding of empathy prevalent within one age group. Moreover, the study raises the question of how historical empathy should be handled in teaching if many future teachers have difficulties in understanding it.