Warning: This article contains SPOILERS for The Walking Dead: Dead City season 2, episode 7, "Novi Dan, Novi Početak".
Season 1 showed signs of his disobedient behavior, as he completely shut down Maggie after she risked her life to save him, but his outburst could be put down to trauma. A teenager spending time in captivity would undoubtedly have a big psychological impact, but season 2 doubled down on his bad attitude. After rejecting his mother's teachings, Hershel started a fire in Dead City that confirmed he was working with the show's central antagonists, and Maggie's attempts to open up to her son have continuously fallen on deaf ears, confirming he is the complete opposite of his parents.
I Get Teenage Angst, But Hershel Agreeing To Have His Own Toe Cut Off Is A Bit Much
His Devotion To The Dama Has Gone A Little Over The Top
The Walking Dead has proven that young characters growing up in the apocalypse are always bound to have flaws, as the likes of Carl, Henry, and Ron suffered from teenage angst, but Hershel agreeing to have his toe cut off feels far more extreme. Whereas Maggie and Glenn would put themselves on the line to protect their loved ones, Hershel sacrificing his toe for a villainous cause completely contradicts his parents and feels like an unnecessary display of loyalty to the Dama, considering how little time they've known one another.
According to the Croat, Hershel willingly gave up his toe, presumably as part of some sort of loyalty test to the Dama's mission. Although she was quick to relate to Hershel's struggles, it still feels strange that the teenager would go to such measures, even though he did take a liking to the Dama. Considering Hershel's comic book counterpart was awful in The Walking Dead's source material, it's not a big surprise to see him going down a dark path, but his edgy decisions are becoming hard to relate to.
It was already frustrating seeing him constantly defy his mother and cause needless confrontations, but the fact that Hershel has once again aligned with the Dama after everything that has happened makes it extremely difficult to root for him.
It was already frustrating seeing him constantly defy his mother and cause needless confrontations, but the fact that Hershel has once again aligned with the Dama after everything that has happened makes it extremely difficult to root for him. Agreeing to have his toe cut off feels like the final straw, as there are almost no lengths he won't go to for the Dama, no matter how ridiculous they might be, proving Hershel's behavior isn't just a teenage phase, it's who he really is deep down.

The Walking Dead: Dead City Season 2, Episode 7's Ending Proves Hershel May Be Too Far Gone
Even After All Maggie's Attempts To Get Through To Her Son, Hershel Remains Fully Committed To Helping The Dama
As if his acts of defiance weren't enough throughout the season, Hershel continuing to assist the Dama in Dead City season 2 is proof he may be too far gone. After her confrontation with the Croat in episode 5, the Dama was presumed dead, but she showed up again at the end of episode 7 alongside Hershel, where she knocked out Maggie. While her new intentions are unclear, they will presumably involve getting back control of the Burazi and the methane operation before continuing her reign of terror in Manhattan, something Hershel seems more than happy to help with.
Even if he didn't know the Dama was going to hurt his mother, Hershel willingly lured Maggie into the villain's trap, making him every bit as bad as her. He may have still shown signs of humanity earlier in the season while protecting Joan, but Hershel's naivety and combative nature have made it easy for the Dama to manipulate him. Sadly, Hershel's mysterious fascination with the Dama in Dead City makes it hard to see a way back for the teenager, and while Maggie may get one final chance to connect with her son, the odds are stacked against her.
It's anyone's guess where Hershel's story goes next, but with Dead City season 2 coming to an end, it seems like nothing will stop him from standing by the Dama's side, suggesting his path to villainy is inevitable in The Walking Dead.