The Walking Dead: Dead City focuses on Maggie (Lauren Cohan) and Negan (Jeffrey Dean Morgan), first introduced in the main series. However, the series also features a storyline about Maggie and Glenn's (Steven Yeun) son, Hershel, named after his grandfather.
The first season saw the young man abducted by the Croat (Željko Ivanek), a former member of Negan's Saviors. The Croat now leads a gang in Manhattan and he negotiated Hershel's release in exchange for the former leader of the Saviors.
After his release, Hershel was very vocal with his mother in regards to her obsession with Negan, the man who brutally killed her husband. The boy felt that he has never been a priority for his mother but her focus has always been on revenge against Negan. This is a hot topic between the son and mother, of which Maggie promises her son to finish things with Negan.
In the most recent episode, "Why Did the Mainlanders Cross the River?" viewers were treated to flashbacks of Hershel's time as captive of the Dama (Lisa Emery), the real leader in Manhattan. The woman treated Hershel very well inspite of him being her captive. She paid attention to him, gave him special treats, and ensure that the boy had ample supplies to continue his drawing hobby.
As season two opens, Maggie discovers a portrait of a woman that her son drew and asked him about it. He told her it was a drawing of a woman he saw on a billboard while he was in NYC. Viewers were quick to recognize the drawing of the Dama. This prompted questions about Hershel's fixation on the gang leader, especially since she removed Hershel's pinky toe and used this as leverage to get Negan to work for her.
The flashback scenes reveal much about the boy's interest in the woman who held him as a prisoner. Unlike his mother, the Dama was attentive and interested in his interests. This explains why Hershel was so intent on returning to the island. He is experiencing a bit of Stockholm Syndrome regarding the woman who treats him well and provides for his needs. These areas in which his mother has completely failed him with her obsession with Negan.
It will be exciting to see what Hershel's next move is now that he is in Manhattan. He feels so strongly about this location that he was willing to betray his mother and New Babylon by lighting the signal fire to alert the Croat.
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