The Walking Dead: Top 100 Moments

81. Gregory Loses His Booze

Episode 705 “Go Getters”

Original Airdate: 11/20/2016

Submitted By: Sarabeth Pollock

From the first meeting with Gregory, the leader of the Hilltop, it’s clear that he’s a snake in the grass. He’s only interested in his own self-preservation and he knows that he has to stay on the up and up because the Savior assigned to the Hilltop is not someone to mess with.

It is in the episode “Go Getters” that we get to meet Simon. We have seen Simon before, but when Simon comes to visit the Hilltop we see that Simon might just be worse to deal with than Negan. Simon doesn’t live by rules. He is out to help himself, and if he can paint himself in a good light for Negan, he will step over anyone and everyone to do it.

When you combine Gregory and Simon you have a very interesting power dynamic at play. It’s not surprising, then, that when the opportunity presents itself, Gregory tries to give up Maggie and Sasha by telling Simon to take the liquor from the closet they were hiding in. Fortunately, Jesus got them out of the closet before they were discovered. But it was a close call, and it goes to show that Gregory is a very dangerous guy to have around.

Of course, Gregory does get punished in the end…he loses his stash of booze to Simon, who is all too happy to take it off of Gregory’s hands.