The Walking Dead: 23 most disliked TWD characters

4. Gregory

The moment when Gregory finally had to pay for his sins for a very satisfying one. In the season 9 premiere, Maggie ordered Gregory’s execution for his attempt to kill her, and it was a great way to start off the new season.

Ever since Rick and the group met Gregory he has been a totally self-serving horrible human being. At times he was almost cartoonish in his villainy which made him a good joke, but when he convinced Earl to attack Maggie and then attacked her himself that was definitely his last chance. Maggie should have killed him a long time ago.

Among Gregory’s many crimes against Maggie and the others was stealing the pocket watch from Glenn’s grave and almost turning over Sasha and Maggie to Simon when they had taken refuge at The Hilltop after Negan’s brutal murder of Glenn and Abe. Gregory was a weak leader and a weak human being. It’s kind of amazing he was able to keep The Hilltop running for as long as he did. But once things started getting rough he proved that he was a bad leader and a bad man who would do whatever he needed to do to keep power and control of the Hilltop.

When he went to The Sanctuary to make a deal with Simon and Negan he had to have been very surprised when The Hilltop residents showed up fight Negan under the leadership of Maggie and Rick. But that proved once and for all that The Hilltop stands with Maggie.