At first glance, Strange Case of Dr. Jekyll and Mr. Hyde is a tale that reinforces binaries. One of these is the self/other binary that is central to David Hume's and Adam Smith's theories of sympathy that conceive of a self imaginatively identifying and experiencing fellow-feeling for an other. However, this notion is complicated because Jekyll and Hyde are the same person. Further, many critics argue that Stevenson actually challenges binary thinking. While Hume and Smith do not challenge the self/other binary in connection with sympathy, trauma theory critics do challenge a self/other binary that lies at the heart of sympathy: the victim/perpetrator binary. Noted trauma theorist Dominick LaCapra develops a method of empathizing called empathic unsettlement where a secondary witness listens with empathy to a victim's traumatic witness while recognizing the difference of his or her position as a witness. He argues that perpetrators may also warrant understanding, but this understanding does not come through empathy. However, one of the hallmarks of empathic unsettlement is that it does not neatly resolve or replace traumatic narratives. Therefore, I argue that empathic unsettlement could also be a useful method for allowing a perpetrator to witness. While practicing empathic unsettlement for a perpetrator may not be worth the risk in real life, performing a thought experiment in literature can test how using empathy might provide a better way to theorize perpetration. Using two witnesses who attempt to practice empathic unsettlement for Jekyll and Hyde, Dr. Hastie Lanyon (who fails), and Mr. Gabriel John Utterson (who succeeds), I will show how empathic unsettlement could be used for both a victim and perpetrator to tease out the complexities of assessing a traumatic situation.