The Walking Dead (2010): Gregory / Characters

Due to the Anyone Can Die nature of the show and quickly moving plots, only spoilers from the current/most recent season will be spoiled out to prevent entire pages of whited out text. These spoiler tags will be removed upon the debut of the following season, and the character bios will be updated then as well. Additionally, character portraits will be updated each half-season with the release of an official, complete set from AMC. If you have not seen the first ten seasons read at your own risk!

Gregory

"I built this place!"

Portrayed By: Xander Berkeley^{Foreign voice actors}

Appearances: The Walking Dead (Seasons 6-9)

Debut: "Knots Untie"

"The Hilltop is my house. I'm still the guy. I've always been the guy."

The leader of the Hilltop community who Rick's group meets to discuss establishing trade. When the group learns that Gregory has been subjugated by the Saviors, Maggie arranges a deal with Gregory so that Alexandria will assassinate Negan in exchange for supplies. Unfortunately, both Hilltop and Alexandria were unaware of the true size of the Saviors, and the latter is cowed into submission. Gregory is annoyed that Rick failed to follow through with his deal, and begrudgingly allows Maggie and Sasha to stay at Hilltop.

To Gregory's dismay, Maggie quickly begins proving herself as a far more competent leader than he could ever hope to be. She throws herself onto the frontlines during a Savior attack, begins getting to know the citizens, and generally bringing out Gregory's worst side for his constituents to see. Gregory is enraged when Hilltop slowly replaces him with Maggie as their leader. He attempts to sell out the colony to the Saviors but finds that their loyalties now lie with Maggie. Gregory spends most of the duration of the Savior War as a prisoner alongside the captured Saviors, Maggie knowing full well he can't be trusted.

After the Savior War, Gregory is allowed to reintegrate into Hilltop, but officially loses the position of leadership to Maggie in an election. Down but not out, Gregory spends the next year and a half trying to rebuild his credibility with Hilltop and to present himself as a loyal ally to Maggie but is only waiting for the right opportunity to kill and overthrow her. Gregory goes for it after Ken’s death, getting Earl drunk to try to kill Maggie. However, Maggie survives and has Gregory executed for treason - and as a staunch reminder to Rick and Michonne what she believes should’ve happened to Negan.

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#-M

0% Approval Rating: Absolutely nobody in Hilltop likes him. At best they tolerated him before Rick and his group showed up. Once Maggie becomes a permanent resident, they look to her for leadership and pretty much stop taking Gregory's shit.
Accidental Misnaming: Zig-zagged. Gregory can't get anyone's name right and always calls them whatever is off the top of his head. According to Xander Berkeley, Gregory is so obsessed with himself that he's entirely ignorant to others around him.
Adaptational Jerkass: While Gregory in the comics at least felt bad and even apologized to the Hilltop after selling them out to Negan, this version of Gregory doesn't even care. If anything, he looks proud.
Adaptational Wimp:
- While Gregory is by no means any kind of badass, his attempt to get people to stop fighting in order to keep their families safe and in the Hilltop Colony did get a few people to give up and go home in the comics. Here, even though we see some Hilltoppers having doubts, nobody does, making Gregory even more pathetic than his comic book counterpart. Even better, on at least one occasion, Gregory made a genuine attempt to help out Rick during a firefight, risking his own life in the process. No such thing is done by his TV counterpart.
- In the comic series, Gregory came very close to killing Maggie; the only reasons his plan failed were that 1) the poison dose was not enough to be lethal and 2) Jesus caught him red handed and managed to save Maggie from whatever backup plan Gregory might have had. Here, however, Gregory unsuccessfully tries to use someone else to do the deed, and when Maggie confronts him directly, he attempts to attack her with a knife instead of using a more subtle approach. Unsurprisingly, it does not end well for him.
Ain't Too Proud to Beg:
- Once he makes his way back to the Hilltop Colony in "Monsters," he pleads for Maggie to let him back into the colony.
- He does this once again on the night of his execution in "A New Beginning."
Alas, Poor Villain: He’s so pathetic when Maggie finally gives the order to hang him, causing him to start screaming for his life despite having realized it won’t work this time, that one can feel a little pity for him. Some other characters also express discomfort with his execution, or at least how Maggie made the decision herself with no other counsel.
Alcohol-Induced Idiocy: In "Worth", he tries to suck up to Simon over tequila. However, when Simon is not interested in giving him a second chance, the inebriated Gregory goes on a hilarious rant about how he believes he is entitled to keep surviving and begins mouthing off to Simon and belittling him. He’s damn lucky Simon merely decked him and assigned him to be his coffee boy.
Ambiguously Evil: Gregory isn't a psychopath like the Governor or Gareth, but his character is entirely questionable. He eventually descends into outright evil in Season 9.
Arc Villain: His tenure as an antagonist on the show lasts for the duration of the Savior arc from Seasons 6-8. His sole appearance after that is the Season 9 premiere in which he’s executed after an assassination attempt on Maggie.
Asshole Victim: After spending roughly two and a half seasons being a misogynistic, sleazy, selfish prick, it's safe to say nobody will miss him now that he's been hanged by Maggie.
"Ass" in Ambassador: Technically, Gregory is the Hilltop Colony's only representative and negotiator, but he's also a grade A Jerkass.
Authority in Name Only: Maggie immediately takes charge of the community after earning the respect of the Hilltop residents while Gregory only gets to keep the meaningless title as the community leader so the Saviors will be fooled into thinking that he's still their benefactor. Even before this, both Alexandria and the Kingdom recognized he was a cowardly idiot, as they both looked to Jesus as their main contact from Hilltop.
Bad Boss: Gregory is an immature, pompous and cruel sociopath who's far more concerned about keeping himself safe than rescuing the captured Craig, and is more than happy (even eager) to leave him to die.
Believing Their Own Lies: He seems to believe every word he says without ever thinking otherwise: Gregory considers himself a heroic pillar of the people who holds Hilltop together. At one point he refers to himself as a "good guy" while ordering a pregnant woman out into danger in the same breath.
Big Bad Ensemble: Downplayed in Season 7. While he's nominally on the side of the heroes, he would prefer not to be, and he's the biggest thorn in the group's side who's not a Savior or a walker. He cannot be trusted and is essentially on the side of the Saviors.
Big Bad Wannabe: He attempts to assassinate Maggie in the Season 9 premiere to take back his place as leader. He fails, and it’s pointed out how stupid his plan was, and he’s hanged by his own people in the community he claimed to have built himself.
Big Eater: Implied by Kal, who mentions that Gregory once ate a little girl's pancakes (presumably in addition to his own). Though Gregory defensively denies this claim, the idea of him prioritizing his food intake over a young child's is hardly surprising.
Big Good: Subverted. He's the leader of the Hilltop, which itself is a good community, but he's so sleazy, spineless and incompetent that Jesus is essentially the one who single-handedly keeps the place safe.
Blatant Lies: He tries to convince Maggie that the Hilltop is doing fine and doesn't need help from Alexandria, when in fact they are under the control of Negan.
Bullying a Dragon: He drunkenly belittles and mouths off to Simon in "Worth."
Butt-Monkey: In his first appearance alone, he is disrespected by Rick, stabbed by a member of his own community, and finally strong armed into a deal by Maggie while still recovering from the wound. Even his own second-in-command doesn't think much of him. It doesn't get any better for him throughout Season 7, where he is bullied into submission by both the Saviors and even his own people, who begin to look up to Maggie as their new leader. Reaches its zenith in Season 8, which sees him shoved down a flight of stairs by Simon (who was the only Savior to personally vouch for him despite the constant bullying), nearly turned away at the gates of his own home for his betrayal, and finally tossed in a pen with a bunch of Savior hostages by some of his own people, who are now completely on-board with Maggie's leadership. Even when he runs back to Simon hoping to get back in his favor, Simon treats him like shit. He's also locked in Barrington House to face the Saviors when they come a-knocking in the Season 8 finale. Finally, he tries to have Maggie killed and is publicly hanged for his treachery.
Casanova Wannabe: He views himself as a ladies' man, openly flirting with both Maggie and Sasha. The result, however, makes him look more like a sexual harasser.
Character Death: He is hanged by Daryl on Maggie's orders as punishment for attempting to have her assassinated in the Season 9 premiere.
Consummate Liar: You'd be surprised at how much of his dialogue consists of lies. A lot of his statements usually regard himself and how he can handle things, when he's clearly out of his depth. A lot of this stems from Believing Their Own Lies, since otherwise Gregory is a pretty poor actor when faced with the likes of Simon.
Crouching Moron, Hidden Badass: Very downplayed, but the fact that he made it to the Sanctuary all by himself deserves some mention. Not as impressive later on when he returns to Hilltop alone, given that it was all a part of Negan's plan for him to deliver fake battle strategies to Rick.
Deadpan Snarker: He throws out a couple of deadpan barbs.
Tara: When people have the chance to do the right thing, they usually step up. I mean, people just —
Gregory: Let me stop you before you break into song, okay?
Death by Adaptation: In the comics, Gregory is hung by Maggie while the conflict with the Whisperers is already underway; in the TV series, he is hung in the Season 9 premiere, before the Coalition is even aware of their presence. Downplayed in that his death takes place not long before the Whisperers are revealed later in the same season.
Dirty Coward: Perhaps his defining character trait.
- When the Saviors came knocking, he rolled over; this is understandable considering Negan's negotiation methods, but he always gives them a mile even when they only want an inch. He also nearly reveals Maggie and Sasha to Simon, but thankfully Jesus saw his betrayal coming.
- He rats out the Hilltop, Alexandria, and the Kingdom to Negan, not even looking upset about it. After it goes south, he has the gall to cry for help, forcing Gabriel to try and save him. He then proceeds to leave Gabriel to die.
- He can flip-flop even in the same breath depending on how the conversation is going. In “Worth”, he goes from respecting Negan to trash-talking him in moments when he learns that Simon has briefly usurped control of the Saviors from him.
- Much like Spencer, he tries to get someone else to do his dirty work so he can take over. He gets a grieving Earl drunk and riled up to kill Maggie for him. Maggie even calls him out for being so weak he can't even murder her right.
Dirty Old Man: He starts hitting on Maggie when they are alone, and later suggests that Sasha have sex with him to earn Maggie a place at Hilltop.
The Ditherer: Gregory can and will change his stance on something at the drop of a hat, sometimes even multiple times in the same conversation. Daryl calls him out on this, saying that Gregory is "talking out of both sides of [his] mouth."
Dumbass Has a Point: In "Do Not Send Us Astray", he's right that bargaining with a bloodthirsty psychopath like Simon over the lives of his soldiers was an empty strategy. It still doesn't stop him from trying to curry favor with Simon later, though.
Establishing Character Moment: Gregory's character is summed up pretty well in his first scene. He proudly boasts, "I'm the boss!" before ignoring Rick's attempts to formally introduce himself by ordering them to head upstairs and get cleaned up. Rick realizes what kind of person Gregory is from this moment alone, and implores Maggie to negotiate with him instead.
Rick: You talk to him.
Maggie: Why?
Rick: I shouldn't.
Everyone Has Standards: Gregory is pretty horrible, but like everyone else he's terrified and disgusted by the Saviors. He would rather not work with them at all and is willing to enlist Rick's help to get rid of them.
- He's also understandably unnerved to discover that the Saviors have conscripted Dr. Carson, who is presently the only medical practitioner in all of Hilltop, to work at the Sanctuary.
Evil All Along: After the post-Savior War Time Skip, Gregory has put on a great show to act like he's changed and become loyal to Maggie. It's all a farce since he's playing a long-term game to usurp her.
Evil Counterpart:
- To Hershel Greene. Hershel was an honorable man, who fought for the people he cared about, and helped others out of the goodness of his heart. Gregory makes others fight for him, treats others horribly, and only helps people out if he gets something out of it. It’s telling that Hershel himself was the Big Good of the prison for the better part of a year, and Maggie herself ends up taking over from Gregory as leader of Hilltop.
- He also doubles as one to Deanna Monroe. Both of them are former politicians who took over as leaders for their peaceful communities because they see themselves as capable heroes who'd guide innocent survivors to safety. However, Deanna was a good-hearted person who wanted to do what's right and consented to Rick's suggestions, while Gregory is too egotistical to even consider advice from Jesus or Maggie.
- To Rick as well. Both were subdued by the Saviors and bullied into compliance, but Rick humiliated himself out of a desire to protect his own people. Gregory wanted only to protect himself, not actually caring about the people under his care. He even mistakes Sasha for a Hilltop resident!
Evil Is Not a Toy: Gregory finds out that trying to suck up to a murderous psychopath does not qualify as guaranted life insurance. When Gregory fails to get the Hilltop fighters to stand down, Simon violently pushes him down the stairs and abandons him to his death. When he later returns trying to wriggle into the Sanctuary, Simon has little patience for him and nearly kills him before reducing him to his coffee boy.
Evil Old Folks: He's in his late fifties to early sixties and proves himself to be very antagonistic towards Rick's group, as well as being a Dirty Coward who has almost no redeeming qualities.
Fake Ultimate Hero: He poses as the Hilltop's greatest hero and noble leader, but in reality, he's not as powerful as he believes he is. According to Jesus, Gregory is actually just some guy who took over as leader and the town has never raised any questions over it.
Faking the Dead: Amusingly, he isn't even aware of this. Rick's group uses a walker head that bears a resemblance to him as a way to get into the Saviors' compound, claiming that they've gone through with the deal and killed him.
False Friend: Has an extremely superficial friendly attitude that Rick and Maggie immediately see through. He tries this again in Season 9 as he pretends to be a loyal ally to Maggie, but it’s a ruse that he’s using until he can find the right opportunity to usurp her.
Fan Disservice: The elderly Gregory is given a Shirtless Scene while lying half naked in bed.
Foil: To Negan.
- Both of them are arrogant, Jerkass leaders who aren't adored nearly as much as they think they are. However, when the chips are down, Negan is shown to be a very charismatic and effective leader without whom the Sanctuary would fall apart in a matter of days. Gregory has a 0% Approval Rating and is cast aside by the populace shortly after Maggie comes along.
- Both of them prove to be an Arch-Enemy of sorts to Maggie (though Negan to a far greater extent given that he killed her husband). In Gregory's case, he also has a vendetta against Maggie because he feels that she is trying to usurp him as leader. In Negan's case, he doesn't have anything personal against Maggie and only killed Glenn because Daryl punched him.
- Both of them start to lose authority over some of their people — Negan over Simon and his crew of rogue Saviors; Gregory over all of Hilltop once Maggie proves to be a far better leader than him. Negan puts a stop to his rebellion in record time; Gregory ends up imprisoned along with some of the captured enemy Saviors.
- Both Gregory and Negan's lives are spared at the end of the Savior War despite them doing absolutely nothing to deserve it. Gregory is not imprisoned for his crimes, while Negan is given a life sentence.
- Maggie has Gregory hanged after being fed up with his bullshit. However, she spares Negan's life when she sees how much he really wants to die.
- Another difference is how they face being shown mercy. Negan does some introspection and begins making strides toward a Heel–Face Turn. Gregory doesn't even try to change his ways and spends the next year and a half plotting to have Maggie killed, which leads to his execution.
- Despite some casual sexist comments, Negan has an admiration of action girls and has employed several women as his high-ranking soldiers. Gregory is threatened by Maggie being in a position of power and talks down to her at every opportunity.
- Negan also has some Villain Respect for Rick's people, including Rick himself. Gregory shows absolutely no respect to anyone unless it'll benefit him, not even bothering to remember anyone's name, and misremembers Rick's as "Rich".
The Friend Nobody Likes: He's technically an ally to Alexandria, but no one particularly likes or respects him. Rick (and Richard from the Kingdom) clearly sees Jesus as the true representative of the Hilltop.
Graceful Loser: Subverted. During the Time Skip between Seasons 8 and 9, an official election was held in which Hilltop chose Maggie as their official leader. Gregory accepts this and begins respecting Maggie as leader of the community... except he doesn’t, and begins a long-term scheme to look like a better person and leader and wait for the right opportunity to overthrow Maggie and retake leadership.
Green-Eyed Monster: He isn't exactly subtle at how envious he is towards Maggie being viewed as the colony's noble leader instead of him.
Hanging Around: He's executed in a public hanging on Maggie's orders after attempting to assassinate her both directly and indirectly.
Harmless Villain: He arranges Maggie's murder even though he would probably be the prime suspect if Earl had actually succeeded. Maggie chastises him by saying that he "can't even murder someone right" and when he then tries to do the job himself, she quickly overpowers him.
Hated by All: Regardless of what side they're on, absolutely nobody on the show is fond of Gregory.
Hate Sink: In his first episode he quickly establishes himself as a slimy, smug, whiny tyrant and an unhelpful thorn in the heroes' side. It only gets worse from there. Xander Berkeley's occasionally hilarious performance makes him slightly more tolerable than his comic book counterpart, though.
Heel–Face Revolving Door: He switches between aligning himself with Hilltop and the Saviors depending on which side he thinks will benefit him the most.
Heroic Wannabe: Gregory deludes himself into believing that he's a great leader who has brought peace for his community, when in reality he's a Dirty Coward begging Negan to spare him.
Hey, You!: He never remembers Maggie's name and simply calls her what's off the top of his head.
Hidden Depths: Any examples of this trope related to him would be implied or inferred at best, but there are a couple:
- During his first meeting with Maggie, Gregory mentions to her that he had previously visited the Barrington House pre-apocalypse and dreamed of working in the room that would one day become his office—particularly admiring a painting hanging on the wall. If nothing else, this shows that at least he is capable of ambition and hoping for things that don't necessarily come at someone else's expense, and is possibly an art lover as well.
- While largely attributed to incompetence, it's hinted that Gregory's having never killed another living human (even for selfish and unscrupulous reasons) suggests that he does at least place some inherent value on human life. This is further suggested when he doesn't act on a potential opportunity to kill Maggie (though he does consider it). Eventually subverted in that he does ultimately make two attempts on Maggie's life later on.
- He does a half-decent job thinking on his feet when Jesus moves Maggie and Sasha from their hiding spot and Gregory has to improvise and present Simon with a bottle of Scotch instead. Though downplayed by the fact that he ultimately erred on the side of betraying them, it's also worth noting that he takes a long time to consider the decision of whether or not to reveal Maggie and Sasha to the Saviors. However, this could also be explained by him being afraid of the potential consequences of harboring fugitives from Alexandria.
Humiliation Conga: When Simon turns up, things go from bad to worse for Gregory. He's pushed around, threatened, has his Scotch and painting stolen, is forced to kneel and is essentially emasculated.
Hypocrite: He criticizes Craig (who has been taken hostage by the Saviors) for his "weakness", despite being a Dirty Coward himself who lets the Saviors walk all over him.
Icy Blue Eyes: He has cold blue eyes that contrast Jesus' Innocent Blue Eyes.
Ignored Epiphany: What’s truly hilarious about Gregory is that for eighteen months, he puts in genuine hard work to appear to be a loyal, helpful member of the community and even earns the friendship of Maggie and Jesus. He knows and realizes the value of showing good character and performing hard work, which is how Maggie became leader in the first place. If something had happened to Maggie, he probably would have been asked to retake command. But he squanders it all with his last coup attempt and proves he’s completely unable to be the loyal, good man he pretended to be.
I Just Want to Be Special: Arguably, the biggest reason why he enjoys being the leader is because others will show him respect and care about his opinion.
Informed Attribute: During the group's first meeting at Hilltop, Jesus describes Gregory as the one who "keeps the trains running on time," to which Gregory adds in a boastful tone, "I'm the boss!" In reality, Gregory is an incompetent jerkass with little to no knowledge or skill in the realm of leadership, and at best is a neutral presence at Hilltop who has managed to not hurt the community more than he helps it. It's strongly hinted that Jesus, who continuously seeks to avoid any implication that he should take over as leader of Hilltop, used Gregory as a scapegoat, knowing that he would be more than happy to take the credit in Jesus' place.
I Regret Nothing: After his latest power play fails, Maggie asks Gregory point-blank if he feels any remorse for all the shit he's done. He tells her that no, he doesn't, because it's gotten him this far.
It's All About Me: He doesn't even care when one of his own people is captured by the Saviors, and is more concerned with the injury that has been done to himself.
Jerkass Has a Point:
- Despite being a sexist pig who’s talking down to Maggie, he points out that Alexandria currently doesn’t have much in the way of supplies and resources to give Hilltop, something Maggie concedes when Gregory notes he has leverage over her due to Alexandria needing Hilltop more than vice versa. Maggie gets to turn the tables on him, however, when she later points out Alexandria is better equipped to battle the Saviors and now has leverage over him (which he concedes as well).
- He's an arrogant, self-absorbed and narcissistic coward, but he is right to see the Saviors as a serious threat, and calls Maggie out on Rick's overconfidence when it came to dealing with them. He also has a point that if the Saviors learn of Alexandria's deal with them, there will be grave consequences for everyone.
- When Negan questions how he can still be in charge of Hilltop if he didn’t know about Maggie leading the Hilltop fighters to Alexandria, Gregory stumbles - since Negan has made the valid point that Gregory doesn’t have the control over Hilltop he says he has - but eventually says that he was already heading for Simon’s outpost to report Maggie’s presence by the time the militia headed for Hilltop on rather short notice.
- Right before he attempts to murder Maggie directly, he taunts her by likening her to Rick's "lackey," and states that she's afraid to go back to Alexandria because Negan is still imprisoned there. While she brushes these comments off at the time, she seems to believe them to be correct the next morning, when Rick visits her at Hilltop and asks her to both give up more food and supplies for the Sanctuary out of the goodness of her heart and visit Alexandria during the same conversation. She rebuffs his request to come to Alexandria, and states that she will only provide the Saviors with additional food if they provide most of the labor to build the bridge.
Jerk with a Heart of Jerk: Gregory is a thoroughly unpleasant, stubborn and self-righteous sleaze who goes out of his way to order Rick around like a child when they first meet. He seemingly becomes a better person following the Time Skip in Season 9, even giving a heartfelt eulogy in honor of the recently deceased Ken. It's really a ploy to take back control of Hilltop from Maggie, and he attempts to have her killed that very same night by getting Ken's grieving father drunk and convincing him to attack her.
Karma Houdini Warranty: Survives the Savior War without any repercussions for his actions. His continued schemes to overthrow Maggie then result in her ordering his execution in the first episode of Season 9.
Karmic Butt-Monkey: He brings all his misfortunes on himself.
Karmic Death: Hanged on Maggie's orders after his repeated attempts to overthrow her.
Kick the Dog:
- Tries to back out of a deal with Alexandria when they propose fighting Negan on the merit that his lost man isn't worth the effort. He just keeps going from there.
- Doesn't show even the slightest concern for Maggie and Sasha or their dead spouses, even when told that Maggie is pregnant.
- He also steals Glenn's pocket watch from his grave, which Maggie promptly punches him for.
- After selling out everyone against Negan, he's extremely lucky that Gabriel even bothered trying to save him. Gregory's response? Stealing Gabriel's car and leaving him to die.
Lack of Empathy: As long as he's not involved, he couldn't care less about what happens to his people. When told Maggie is pregnant, he derisively says it was her mistake. A truly stunning example occurs in the Season 9 premiere, when he makes a big speech memorializing Ken, sits with his grieving parents... and gets Earl drunk and plants the idea to kill Maggie so that he can retake control.
Large Ham: He's a rather pathetic, overly brash and dramatic whiner at the worst moments and as a result, he infuriates other characters and even the audience as well.
Laser-Guided Karma: When he tries to sell out Maggie and Sasha to Simon, Jesus tricks him into instead giving up his own prized possession of scotch. He is then forced to kneel in front of the Saviors, and Jesus makes it clear that from now on he has Authority in Name Only.
Laughably Evil: As a villain, he's very easy to laugh at due to being rather pathetic and incompetent, not to mention an over-the-top Drama Queen.
The Leader: Of the Hilltop. Not a particularly good one, though.
Leader Wannabe: After losing his position as leader to Maggie, he grows desperate in his attempts to get the position back.
Lean and Mean: He's a skinny old man and a totally deceitful and manipulative jerk.
Make an Example of Them: His execution by hanging is Maggie’s way of flipping the bird at Rick and Michonne for sparing Negan. The pair clearly take the hint and are uncomfortable with it.
Malicious Misnaming: It's implied there are times where he intentionally gets Maggie's name wrong because he thinks doing so will knock her down a peg or two.
Manipulative Bastard: He takes advantage of Earl, who is grieving the loss of his son, by getting him drunk enough to talk him into trying to assassinate Maggie.
A Man of Wealth and Taste: Gregory lives in a McMansion, wears a nice suit, and prefers to negotiate in his office.
Mean Boss: Jesus makes no secret about what a prick he is. Gregory distances himself from his own people, sacrifices them at the drop of a hat and puts himself above all others.

N-Z

Narcissist: Gregory only cares for himself and will say anything to ensure his own survival.
Never My Fault: Gregory doesn’t see anything going wrong as his fault and is quick to defer blame to literally anywhere else he can.
- When he's caught having stolen Hershel's watch from Glenn's grave, his excuse is that, "it's a fine watch, doesn't need to be left out in the rain."
Nice Job Fixing It, Villain: A recurring theme around Gregory is how his attempts to make things better for himself always end up shooting himself in the foot.
- Bullying and demeaning Maggie in their meeting right before getting stabbed in the stomach convinces Maggie of his true nature - that he's a weak, cowardly man with an act that she can now see through, and thus she's able to use his earlier advice regarding leverage to broker the deal between Alexandria and Hilltop.
- Attempting to sell out the hiding Maggie and Sasha, failing Jesus's Secret Test of Character, finally convinces Jesus that he's not worth listening to in the slightest and sets him up to start grooming Maggie for the role of leader.
- Going to the Sanctuary to order the Hilltop fighters in the attacking militia to stand down only proves that he doesn't care about his constituents' well-being, and they swear loyalty to Maggie on the spot. It removes Gregory from his position of power and incurs the wrath of Simon when he sees that Hilltop's people are no longer loyal to him.
- After the Savior War, he calls for an election out of some delusion that he's going to be appointed leader again. All it does is ensure that Maggie, the woman who actually led Hilltop during their successful war against the Saviors, receives a legal election to the office of Hilltop's leader, unlike Gregory who simply appointed himself leader at its founding.
- Finally, enacting one final coup attempt by using Earl to try to kill Maggie quickly unravels when Earl is stopped, and Maggie catches him. It destroys the goodwill he had built up for himself over the last 18 months since the election, and while some survivors express discomfort with his execution, nobody tries to stop it.
No Last Name Given: Unlike Jesus, we never find out what Gregory's last name is.
Non-Action Guy: He's not a fighter. In fact, Season 7 reveals that he's never even killed a walker.
Not-So-Harmless Villain:
- He's a weak coward, but he does have one dire weapon on his side - information. When it's clear Maggie and her friends are becoming the leaders of Hilltop and usurping him, Gregory implies that should it not be stymied, he will rat them out to the Saviors. Until the season finale in which the masquerade is cast off anyway, it's a serious threat to the group as they're not quite ready for open rebellion yet.
- He's not a fighter, but he is still quite the talker. While most people don't fall for it, he uses it to great effect on the grieving Earl and Tammy, and nearly succeeds in using Earl to kill Maggie for him.
Not Worth Killing: According to Maggie he isn't, at least not yet. Her mercy runs out when he tries to have her assassinated in the Season 9 premiere.
Pet the Dog:
- Subverted big time in that his attempt to do this fails epically. One, he's never killed a walker before, so he's helpless when attacked by a walker he tried to kill, and only did it because his fragile ego was being wounded because a pregnant woman didn't really need his help. Two, his offer to watch Maggie's back outside the walls is also a window of opportunity for him to consider killing her. Three, this all is hardly charity considering the Pet the Dog moments of other, more dangerous villains like The Governor and Negan completely outrank his pathetic endeavor.
- Once again subverted when he takes the time to console the Sutton’s for the loss of Ken, sitting with them and sharing a drink. It’s all an act to get Earl drunk enough to try to kill Maggie for him.
Politically Incorrect Villain: Doesn't seem to think much of women in power, as he quickly begins trying to bully and subdue Maggie when they're alone for the first time. Later, when he meets with Maggie outside Hilltop’s wall and a walker approaches, Maggie insists she’s got it, but he goes to kill it instead - only because he's offended that a pregnant woman doesn't need his help.
Psychopathic Manchild: Gregory acts very stubborn, whiny and bratty despite being an old man. When he’s thrown into the Savior pen, he’s whining and crying like a baby protesting that he didn’t do anything.
Public Execution: He ultimately is hanged by Maggie and Daryl for all of Hilltop's residents to see.
Quickly-Demoted Leader: It doesn't take too long for him to lose his leadership to Maggie.
The Quisling: He tries to be as compliant and accommodating with the Saviors as possible to spare himself and his community (though mostly himself) from further harm.
Redemption Rejection: After his death, Maggie notes that Gregory had been given several chances to redeem himself and never took advantage of any of them.
Rich Jerk: Heavily implied. Gregory wears a nice suit, lives in a McMansion, and orders others around. In fact, the first thing he does is order Rick's group to clean themselves up since he doesn't want them getting his house filthy.
Robbing the Dead: He actually has the nerve to pilfer Hershel's pocket watch from Glenn's grave. Maggie is understandably furious.
The Rival: He sees himself as one to Maggie, when in reality she barely even registers him as a threat.
Running Gag: In a nod to the comics, he gets Maggie's name wrong twice over the course of a single scene. He is so aloof from his people that he can't get anybody's name right.
Screw This, I'm Outta Here: Knowing he's fallen out of favor with Hilltop, Gregory flees the community when Henry causes all the imprisoned Saviors to escape. Unlike them, however, Gregory heads straight for the Sanctuary to try to patch things up with Simon. He ends up being forced to flee again, this time back to Hilltop, when Simon's mutiny against Negan fails two episodes later.
Shut Up, Hannibal!: In his last moments, he claims Maggie is only hanging him at night because she’s ashamed of executing him, clearly trying to talk his way out. Maggie coldly replies that he’s wrong, and she isn’t ashamed, and has him killed moments later.
Slimeball: He's an incredibly sleazy sycophant and tries to hit on Maggie the moment they meet. He also shamelessly looks down Sasha’s shirt when she asks what she needs to do to keep Maggie in Hilltop and implies she could earn it with sexual favors.
Small Name, Big Ego: He's very full of himself and actually deludes himself into believing that he's a noble hero. Case in point, he tells Jesus that he took a stab wound for his community while Jesus didn't sacrifice as much. Said wound was from an assassination attempt on his life which he never saw coming while Rick's group incapacitated the actual assailants.
Smug Snake: He's clearly deluded himself that he's a powerful leader, but in reality, he's little more than a subordinate to Negan. Maggie is also easily able to strongarm him into giving up half of the Hilltop's supplies.
The Sociopath: A low-functioning example. He's a selfish manipulator with a complete Lack of Empathy for anyone but himself, and views human lives as expendable unless they directly benefit him.
The Starscream: An interesting example in the fact that he wishes to put down someone who is essentially usurping him. He is heavily tempted to kill Maggie in "Something They Need", who has been slowly but surely rising as a leader of Hilltop. He makes a more credible attempt in the Season 9 premiere when he gets Earl drunk to kill Maggie for him, but thankfully Maggie is saved and responds by executing him.
Stupid Evil: His last attempt on Maggie's life falls squarely into this since, on the off chance Gregory had actually succeeded, he would surely be the prime suspect.
Sudden Sequel Death Syndrome: He actually manages to survive the war with the Saviors, only to die in the very first episode of Season 9.
Teeth-Clenched Teamwork: He eventually agrees to ally with Alexandria and give them half of his resources in exchange for them assassinating Negan.
This Cannot Be!: He truly cannot comprehend the idea that he is not a beloved, respected leader. When Negan questions how Gregory is still in charge of Hilltop if he didn't know about Maggie leading a group of fighters to Alexandria, Gregory is reduced to a spluttering mess as he begins realizing that he has lost control. When his attempt to convince Hilltop to surrender fails, he is nearly catatonic until Simon pushes him down some stairs. He ends up wailing like a baby when he's imprisoned with the Savior captives, crying that he didn't do anything despite having sold his people out to Negan. And finally, he cries desperately that he doesn't deserve to die for his assassination attempt on Maggie.
Token Evil Teammate: He's the only resident of the Hilltop Colony to not immediately jump on with the war effort against the Saviors and starts to lose more and more trust with his fellow survivors every appearance.
Took a Level in Jerkass: He manages to sink to new lows in the Season 9 premiere when he manipulates the emotionally distraught Suttons and tries to kill Maggie twice.
Undignified Death: He dies crying and begging while all his former people watch and nobody objects.
Ungrateful Bastard: After Maggie and Sasha save his community from a walker attack instigated by the Saviors, he still wants to kick them out of Hilltop and nearly rats them out to Simon in order to get back in the good graces of the Saviors.
Unwitting Pawn: He had no idea that Negan was counting on him to deliver a fake battle plan to Rick.
Villainous Breakdown: After Earl's murder attempt fails, he decides to take matters into his own hands and kill Maggie himself, while also ranting about how he was the one who built Hilltop and how he'll frame Maggie's death to make it look like she was the one who had attacked him. When he’s on the horse that will ultimately help execute him, he sobs like a baby trying to weasel his way out one last time, but when Maggie refuses and orders his execution, Gregory screams and hollers for his life all the way to his last breath.
Villains Want Mercy: After trying to have Maggie killed twice, he breaks down and pleads for his life just before he is hanged.
Villain with Good Publicity: He's not an outright villain, but he's a slimy and spineless jackass who Jesus mentions is well-regarded by the Hilltop denizens. This starts to break down as Maggie proves herself to be a far more capable, compassionate leader in her own right, and the denizens of Hilltop begin slowly gravitating towards her. By Season 9, as he’s faking a Heel–Face Turn, he does begin to be regarded as a loyal member of the community again. However, when he tries and fails to have Maggie killed, nobody raises any objections to Maggie’s decision to execute him. The only thing anybody questions is how Maggie made the decision on her own - not whether or not he deserved his fate.
We Can Rule Together: He strikes up a conversation roughly to this effect with Maggie while sitting with her in her (formerly his) office, once it's become clear that he's not going to regain leadership just on his own; he reasons that she needs his expertise to run Hilltop efficiently, and he's "already in the room." Maggie doesn't bite, insisting that he's only there with her so that she can keep her eye on him. Given Gregory's low opinion of women in power, and his established dislike of Maggie, it's likely that he eventually would've tried to usurp her co-leadership from her even if he did initially uphold his end of the deal.
What Happened to the Mouse?:
- Heads for parts unknown with Kal in the penultimate episode of Season 7 and doesn't return before the season ends. Maggie and Jesus suspect he's going to rat them out to the Saviors, but we don't learn for sure, and even if that's his intention, it's moot since the Saviors learn of Hilltop's resistance in the season finale anyway. The eighth season premiere confirms that he went to try to rat out Maggie to the Saviors. However, none of the Hilltop fighters heed his word and back down when asked.
- At the end of “Do Not Send Us Astray”, Gregory flees Hilltop with the Saviors being led to freedom by Jared. However, he doesn’t reappear when Rick and Morgan encounter them in the next episode, leaving his whereabouts unknown. He returns in “Worth”, having made it to the Sanctuary in a desperate attempt to regain Simon’s favor.
What You Are in the Dark: He has an opportunity to try and murder Maggie outside the walls. He doesn't take it. Keep in mind he probably couldn't have succeeded anyway, and the fact that he was considering murdering a pregnant woman to begin with really speaks volumes.
Wild Card: As the conflict with the Saviors grows more intense, Gregory's loyalty to the alliance between Rick's group and Negan's Saviors starts to muddy where he stands.
Would Hurt a Child: He strongly considers killing the pregnant Maggie.
Yes-Man: He pretty much remains Simon's personal suck-up in order to remain in his favor. That is, until he fails to convince Hilltop to side with The Saviors, causing Simon to berate him and then push him down a flight of stairs.

"Earl attacked you because you got his son killed! You blamed me. You attacked me. And I defended myself!"

Characters / The Walking Dead (2010): Gregory

Gregory

Portrayed By: Xander Berkeley^{Foreign voice actors}

Appearances: The Walking Dead (Seasons 6-9)

Debut: "Knots Untie"

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Characters / The Walking Dead (2010): Gregory

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Gregory

Portrayed By: Xander BerkeleyForeign voice actors David García Vázquez (Spanish dub), Yutaka Nakano (Japanese dub), Klaus-Dieter Klebsch (German dub), Stefan Godin (French dub), Fabrizio Pucci (Italian dub), Pavel Rímský (Czech dub), Sándor Rosta (Hungarian dub)

Appearances: The Walking Dead (Seasons 6-9)

Debut: "Knots Untie"

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Portrayed By: Xander Berkeley^{Foreign voice actors}