Why Hershel Draws The Dama & New York In The Walking Dead: Dead City Season 2

The Walking Dead: Dead City season 2, episode 1 offered a closer look at Hershel's drawings of the Dama and New York, hinting at why he drew them. Of all the characters in Dead City, Hershel has been a core figure since the very start, with his capture by the Croat the inciting event for the whole series. Taking the boy to New York City, the Croat demanded that Maggie bring Negan to him in exchange for her son, prompting her to recruit the former antagonist for a would-be rescue mission.

However, when Dead City season 1 ended with Hershel getting back to his mother, he was clearly unhappy to have been returned. Part of this was because he felt like Maggie couldn't let go of Negan killing Glenn over a decade ago, saying he's tired of the conflict she still has with him. However, Dead City season 2 hints that there's a deeper reason for him not wanting to come home, especially after having focused so much on the drawing he'd made of both his true captor, the Dama, and New York City.

Maggie Is Right, The Dama & New York Have A Hold Over Hershel

It Seems Like Hershel Wants To Go Back To Manhattan

It's unclear what Hershel's interactions with the Dama were like when she held him captive in Manhattan. However, it was confirmed that she took one of his toes while he was with her. She shows it to Negan in the season 1 finale, promising that, if he doesn't help her unite Manhattan under her rule, she'll invade the Bricks and kill Hershel. While this sways Negan to become his old self to keep the boy safe, it also implies the Dama doesn't care much for Maggie's son, except to use him as leverage to get what she wants.

Even so, Hershel clearly feels a different connection with her, as he drew a detailed portrait of her while he was in captivity. When Maggie confronts him about who she is in Dead City season 2, episode 1, he lies and says she's someone he saw on a billboard. He seems keen on keeping her identity a secret despite her removal of his toe and keeping him a prisoner. But, with season 1 showing very little regarding his time being captured, there's no way of knowing why he decided to draw her until the show offers more context.

As for his drawings of New York City itself, one of them is of what appeared to be a dilapidated store, signaling he may have walked around inside the city. However, his standout sketch is one of the Manhattan skyline, showcasing buildings with large, circular structures built out of them. While Maggie's NYC hat gift from the end of season 1 was an attempt to connect with her son, his connection clearly appears to be to the city itself. His drawings act as an extension of that draw, with something likely having happened there to make him open to returning.

Back In Dead City Season 1, Hershel Said He Felt Safer In New York

In Season 2, He's Clearly Trying To Get Back

After Maggie manages to get him back to the mainland, Hershel relents that he actually felt safer while he was in New York City. His anger appears to have been not only driven by wanting Maggie and Negan's feud to finally stop, but also because he was seemingly treated well by the Dama. This is despite the fact she removed his toe, and despite spending much more time with his mother in The Walking Dead's timeline. Somehow, something that happened to him in the city made him feel safer there, although it remains unclear what exactly transpired.

What is clear, though, is that he's trying to get back to Manhattan. When Maggie reveals that she's joining the New Babylon Federation on their scouting mission to learn more about the island's methane production, Hershel wants to go with her. However, she denies his wishes, scared that New York City has a hold over him that he's not being honest about. However, the end of season 2, episode 1 indicates he's going to go regardless, hinting his determination to return is connected to his drawings.

As Dead City season 2's trailer reveals, Hershel does, in fact, return to Manhattan against his mother's wishes. While he'll end up reuniting with her in the city at some point, one curious moment in the trailer sees him together with the Dama. It's unclear if this is happening during the events of season 2, or if it's a flashback to when he was captured by her group. However, the pair seem to be working together, signaling they truly did have a benevolent connection with each other while he was being held prisoner.

Has Hershel Found A New Mother Figure In The Dama?

Perhaps His Loyalties Are About To Be Tested

Although it's unclear why Hershel feels a strong connection to the Dama, it's possible that she has become some kind of mother figure for him since meeting her. His interactions with Maggie make it clear the pair didn't have the best relationship while he was growing up, potentially making it easier for him to find parental figures in other people. Even though the Dama took his toe, it's possible the pair formed a bond while he was captured. Since he managed to draw her so well, it's within reason to believe their relationship wasn't antagonistic.

However, this could also mean his loyalty to Maggie is going to be tested, especially if he meets the Dama again. Since she's trying to unite Manhattan's survivor groups against New Babylon's encroaching invasion, Hershel might feel like he can't side with his mother anymore because of her involvement with them. What this means for the future is unclear, but, if Maggie remains loyal to the Federation, then it's possible the young man will have to choose where his allegiances lie. With New York City drawing him in, it's easily possible he winds up with the Dama.

Hershel's drawings of the Dama and New York are a reflection of his positive feelings about Manhattan, despite having been kidnapped and having a toe removed. There's lots of context to his capture that The Walking Dead: Dead City hasn't explored yet, with season 2 likely adding new details that emphasize why he is so drawn to the city. With his decision to go there now set in stone, his feelings will likely be explored much more going forward, contextualizing whatever decision he makes about who he's truly loyal to.