After teasing it in The Walking Dead: Dead City season 1, the show finally explained what is behind Hershel and the Dama's dynamic. Season 2 reveals that the Dama convinced Hershel to essentially become a double agent for her by showing him her plans to make New York City better while also showing genuine interest in him. Given how we have seen Maggie's obsession with Negan over TWD Universe, I feel like that was a great way of showing how Hershel fell for the Dama's words. I look forward to how the show handles his allegiances throughout season 2.