Gregory is the worst possible leader for Hilltop on The Walking Dead

Sasha and Gregory - The Walking Dead, AMC
Sasha and Gregory - The Walking Dead, AMC /

On The Walking Dead, Gregory is the worst leader that the group has come across. Sure, The Governor killed most of his people, but at least he knew the names of the citizens.

On the surface it might not seem like Gregory is the worst leader that the group has come across on The Walking Dead. The Governor ended up killing most of his citizens. Then he led another group to their deaths fighting Rick for the prison. He was a tough leader but at least he made decisions trying to keep people safe. He just made the wrong choices.

Father Gabriel, the leader of his flock of faithful, got them all killed when he refused to let them in the church. He holed up in the church and used all the food and supplies gathered for the poor while his parishioners died outside. He wasn’t a good leader, but he wasn’t the worst leader.

Gregory is the worst leader because will use up everything that Hilltop has, including all the people there, to make his own life better. Ultimately he will destroy the colony unless Maggie or someone else takes over the running of the colony. Consider the qualities that make a good leader. Gregory has none of them.

Being A Good Person Vs Being a Good Leader

There is a big difference between being a good person and being a good leader. The best leaders, like Rick, are both. But it’s not actually necessary to be a good person in order to be a good leader. Negan is a terrible person but a good leader. Sanctuary runs smoothly. The people have food and supplies. The community is secure. He keeps people in check, even though he does it in ways that are morally questionable if not downright cruel. He gets results even though he uses extreme measures to get them.

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There are a lot of reasons to dislike Gregory. He’s arrogant and rude. He won’t learn Maggie’s name, or the names of his people. He is selfish and self-indulgent. Also, he’s an opportunist. Those qualities make him a bad human being, but that’s not why he’s a bad leader. He’s a bad leader because he doesn’t have any of the qualities that a good leader needs like:


Xander Berkeley as Gregory - The Walking Dead, AMC
Xander Berkeley as Gregory – The Walking Dead, AMC /

People respond to honesty. The history of politics is littered with failed leaders whose lack of honesty caused them to fail. Gregory is a liar who will lie in any situation to anyone. He lied to Maggie and Sasha. He would have turned them over to the Saviors in a heartbeat if it was to his advantage. He lied to the Saviors. He lied to his own people. A good leader has to be honest or his people won’t want to fight for him or work for him.


Gregory is only committed to taking care of himself. He’s proven that he will sell out anyone to make his life better. He doesn’t care if Hilltop thrives. The personal safety and happiness of the people at Hilltop don’t concern him. He tried to kick out a pregnant woman who needed medical care. And he did it to save his own skin, not to protect Hilltop. He only cares about the people of Hilltop as long as they can protect him and provide for him.

A good leader does the opposite. Leadership means taking care of your people before yourself. Leadership is almost like parenting. If you’re not willing to put your people’s needs first, like a parent puts a child’s needs first, you will never be a good leader.


Gregory, Sasha, and Maggie - The Walking Dead, AMC
Gregory, Sasha, and Maggie – The Walking Dead, AMC /

A person that wants to lead has to be the kind of person that will step up in times of danger or crisis. In the world of The Walking Dead danger is everywhere. Leading a community means assessing threats and developing security plans to meet those threats.

When The Saviors attacked Hilltop in the middle of the night in “Go Getters” Gregory hid in the house. Maggie, Sasha and Jesus jumped into action to save the people of Hilltop while Gregory tried to protect only himself. He’s a coward. Cowards are never good leaders.

Post Apocalypse Leadership Skills

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In the world of The Walking Dead Gregory isn’t just a weak leader. He’s a dangerous one. His inability to deal with conflict combined with his total lack of security planning leaves Hilltop very exposed. Jesus admitted that they have very few fighters. And Hilltop has almost no weapons except for spears and some farm tools. They have very few guns. But instead of focusing on security Gregory is focused on getting things for himself.

A good leader would be training fighters, scavenging for weapons and ammunition, and looking to make deals that will increase security for the colony. When Rick and Maggie approached him last season about trading weapons for food Gregory said that Hilltop didn’t need weapons. Every community needs weapons in a world full of walkers and people like Negan.

Next: Burning vs burying the dead

Gregory Won’t Last Long

Now that Maggie and Sasha have settled at Hilltop and recruited Jesus to help them Gregory won’t be leading Hilltop much longer. Maggie is a born leader. Sasha and Jesus are the capable, strong and intelligent people she needs to help her turn Hilltop into a thriving community. Once Maggie takes over and starts working with Rick and Team Family at the Safe Zone Deanna’s dream of rebuilding society might actually happen. One thing that is certain is that in the Walking Dead Gregory and weak leaders like him will never stay in power for long.