The Dead City star reveals how heartbreak pushed Dillard beyond his breaking point.
Summary
– Negan destroying Dillard’s walker family shattered their growing friendship
– Dillard targets Maggie because he wants Negan to experience the same pain
– Jimmi Simpson believes Dillard’s upcoming ending perfectly completes his story
Warning: This article contains major spoilers for The Walking Dead: Dead City Season 3, Episode 7.
Dillard reached his breaking point during the episode “Hourglass” of The Walking Dead: Dead City, turning his pain into a dangerous mission against Negan and Maggie.
The relationship between Dillard and Negan had developed into an unexpected friendship. The two men connected because both understood what it felt like to be judged and misunderstood by others.
Jimmi Simpson explained that Dillard had found peace living inside his bar with the walkers he considered family. Their intentions were predictable, and he did not have to worry about them lying or betraying him.
Negan helped Dillard believe that human relationships could still have value. Their time together allowed Dillard to become comfortable around another living person after years of isolation.
That progress ended when Negan killed Dillard’s walkers. Simpson said the loss destroyed not only Dillard’s unusual family but also the friendship that had helped him reconnect with humanity.
Dillard responded by cutting his own face and blaming Negan. Simpson viewed the act as a physical representation of the character’s emotional collapse and desire to make Negan experience similar pain.
His breakdown became deadly when he killed Renata and announced plans to target Maggie. Simpson explained that Dillard does not blame Maggie for what happened but understands how important she is to Negan.
Taking Maggie away would allow Dillard to hurt Negan in the deepest way possible. His revenge is driven by heartbreak rather than anything Maggie personally did to him.
Dillard also returned to wearing his old police uniform. Simpson did not view it as a traditional villain costume but as the character retreating into a former version of himself.
The uniform represents a time when Dillard believed humanity was destructive and beyond saving. Losing his walkers and friendship with Negan convinced him that nothing had changed.
Simpson believes every extreme decision makes sense from Dillard’s damaged perspective. The character sees his actions as a justified response, even when they appear completely irrational to everyone around him.
The actor also praised Jeffrey Dean Morgan, saying their off-screen friendship helped make Dillard’s connection with Negan feel genuine. That bond made their falling out more emotionally powerful.
Simpson avoided revealing what happens to Dillard in the season finale. However, he described the character’s ending as irreplaceable and said the journey as a whole was one of the reasons he accepted the role.
