In the penultimate episode of "The Walking Dead: Dead City" Season 3, titled "Hourglass," Dillard (Jimmi Simpson) suffers a devastating breakdown after Negan (Jeffrey Dean Morgan) kills both of his pet walkers, shattering their friendship and pushing Dillard towards a violent, revenge-driven turn. The moment marks a significant shift for the character, who had found peace living among walkers rather than people, and sets up further conflict as the season heads towards its finale, with Dillard reportedly now intent on harming Maggie as well.

Speaking to Collider, Simpson explained that Dillard's contentment stemmed from a traumatic past as a police officer disillusioned by human cruelty, which made him feel safer among predictable, honest walkers. His bond with Negan formed because both men felt like outsiders, and Simpson described their relationship as one that could have led to a "real sweet life" together had it not been derailed. Instead, Negan's killing of the walkers—following an earlier scene involving a bloodied character named Fabian—triggers an irreparable break, with Simpson praising Morgan for grounding the scene emotionally despite its dark turn.