The Worst Decisions In The Walking Dead, Part II

Season Eight: Gregory sides with the Saviors over Rick.

I knew that, sooner or later, I’d get to Gregory…

I feel like there were a decent number of bad decisions you could look at in season eight — Daryl and Tara deciding to drive a truck into the Sanctuary, Carl deciding to put down a walker with Siddiq, Rick trying to go back to the Scavengers — but, I think the worst, in terms of sheer stupidity, of the blatant obviousness of its eventual failure, and in how quickly it backfired on the person who did it, I have to go with Gregory siding with Negan over Rick.

Just as a refresher, in the season eight premiere episode, “Mercy”, as Rick, Maggie, and Jesus led a contingent of soldiers from Alexandria, Hilltop, and The Kingdom to confront Negan at the Sanctuary, Negan presents Gregory, who attempts exercise authority over the citizens of Hilltop and demand they stand down, claiming the community is allies with Negan. Not surprisingly, they all reject this. That play having failed, Gregory is immediately deemed surplus to requirement by Simon, who literally kicks him out of the Sanctuary, leaving him to his fate.

Being the snake in the grass that he was, Gregory betrayed Father Gabriel, who went back to save him (Because Father Gabriel is a good person), stealing Gabriel’s car, and leaving him to die.

Of course, when he returned to Hilltop, expecting things to go back to the status quo, he wound up getting imprisoned by Maggie for his betrayal.

Basically, the stupid sneak tried to cut and run about three times in the space of a few minutes, and wound up being treated like a common criminal in the very community he used to lead. If that isn’t a massive backfire, I don’t know what is.

Now, again, I know there were decisions that had bigger negative impact than Gregory’s, but, come on: Gregory’s selfishness boomeranged on him so quickly and in such spectacular fashion, how could I not choose this?!

A long time ago, I defined what I call a “That Guy” — Basically, a person who is selfish even to the point of their own detriment — and, the more I think about it, of all the characters we’ve seen in The Walking Dead (And, this incident proves it), Gregory is, ironically enough…that guy.