Negan (Jeffrey Dean Morgan) is very much an acquired taste for a lot of fans ofThe Walking Dead, with a penchant for brutal honesty and an ugly tendency toward betrayal and violence. Yet, as one of the show’s most complex characters, it’s impossible to sum him up as a straightforward villain.

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This is a character who is single-handedly responsible for one ofThe Walking Dead’smost shocking deaths with Glen, who he brutally murdered in a move that left some fans alienated from the franchise. Though he has come a long way since those days, it’s still hard to call him a hero. If anything, it’s difficult to tell quite what he’s going to do, making him the confirmed wild card of the series.

He Left His Wife When She Needed Him Most - Season 10, Episode 22 “Here’s Negan”

Delving into Negan’s background promised to be a bumpy ride, but it added some humanizing characteristics as we saw how much his wife Lucille truly meant to him. Though he neglected and cheated on her, he is destroyed by his own failure as a husband, and he vows to stay by her side as she slowly dies from cancer. When they run out of her chemotherapy medication, she begs him to stay with her as she knows she’s going to die. He can’t accept that, so he leaves, trying to do the right thing but ultimately ruining his only chance to say “goodbye.”

When it comes to great episodes of the series, this is an all-timer. Fleshing out a complicated character’s backstory by showing him at his most desperate, this episode still refused to absolve him of his actions. In short, this was the origin story that Negan deserved. Having Negan’s wife played byJeffrey Dean Morgan’s real-world partner Hilarie Burtononly seemed to add to the emotional impact of the episode.

Negan (Jeffrey Dean Morgan) and Lucille (Hilarie Burton Morgan), laying together on a bed while Lucille wears a pink wig in The Walking Dead

He Was Devastated By Carl’s Death - Season 8, Episode 16 “Wrath”

Negan was a truly terrifying antagonist, butRick Grimes has likewise made some tough decisions. When the two of them finally square off after a lengthy build-up over multiple seasons, it was destined to be a battle to remember. Yet, it didn’t play out quite how we thought it was going to.

After the rage that Rick had been forced to swallow when it came to Negan, it might not be a huge surprise that he won the fight. It’s how he won that came as a shock. After befriending Rick’s son Carl, Negan is genuinely disturbed to hear the boy has died, and it causes him to fall. This isn’t the first glimpse of Negan’s softer side, but it certainly rates on the list of times that his sensitivity led to his downfall.

The Walking Dead Season 8 Wrath

He Is Disturbed By Idolization of Violence - Season 10, Episode 5 “What It Always Is”

Negan is free from the cell he has spent years in at Alexandria, and he decides to get as far away from it as he can. Eventually, he realizes he’s being followed by a young man named Brandon, the son of one of the Saviors. Brandon idolizes Negan and assumes he’s going to reform the gang, while Negan has changed and no longer sees the sense in fighting for leadership of a group of killers.

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They come across a mother and her son, and Negan bonds with them, promising that he will see them to the Hilltop where they can live in relative peace. He sends Brandon away, disgusted and annoyed by him misunderstanding his actions with the Saviors as worthy of reverence. Brandon kills the mother and her son, having misread Negan’s rejection as a test for him to prove his ruthlessness. This causes Negan to snap, and he kills Brandon, showing both how much and how little he has changed over his years at Alexandria.

He Hit Rock Bottom in Prison - Season 9, Episode 5 “What Comes After”

After a lengthy absence, Maggie returns to Alexandria, and convinces a reluctant Michonne to hand over the keys to Negan’s cell. She goes in with the intention to kill him, but soon starts to realize that Rick’s decision to force Negan to live with himself wasn’t necessarily one born out of kindness.

Negan is happy to see Maggie as he hopes she’ll put him out of his misery. He viciously taunts her over Glen’s death, but when she drags him out to get a better look at him, she is dismayed to see a man who is absolutely broken by the things that have happened to him and the things that he has done. Leaving him to wallow in his own misery, Negan is not given an easy out, and he is forced to begin rebuilding his broken spirit.

The Walking Dead Season 10 What It Always Is

He’s Judith’s BFF - Season 9, Episode 16 “The Storm”

One of the most surprising friendships of the series is Negan’s bonding with Judith Grimes. Despite the complications of his relationship with Rick, Negan has always had a soft spot for children. Recognizing Judith’s bravery as well as her innocence, he is cordial with her throughout his stint in the cell at Alexandria.

This episode shows Negan at his most antagonistic as well as his most heroic. When Father Gabriel comes to realize he needs to let Negan out of his cell before he freezes to death during a blizzard, Negan openly taunts the man who is saving his life. Yet, when Judith runs out into the snow after Dog, he is hot on her heels and ultimately returns her to a grateful Michonne.

The Walking Dead Season 9 What Comes After

Hooking Up With Alpha - Season 10, Episode 9 “Squeeze”

Season 10 showed Negan truly all over the place, and he even joined the Whisperers after they brutally murdered many of the residents of the Hilltop and Alexandria alike. Getting close to Alpha was all a part of his master plan, but getting involved with her romantically was a surprise for us all.

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After spending much of his time with the Whisperers attempting to sow dissent and paranoia, Negan is surprised when Alpha takes him out to a field and orders him to undress. Citing that he’s a crass man, and she’s going to give him a crass reward, the two embrace. This was a surprising turn of events, perhaps for none so much as Negan himself. Alpha remains one of the most terrifying villains the crew has ever faced, but Negan didn’t balk at her advances, showing yet another surprising side to his personality.

…And Then Killing Alpha - Season 10, Episode 12 “Walk With Us”

Well, nothing lasts forever! While Negan teaming up with Alpha was a bit of a shock, it was a lot less surprising when he was revealed as a double agent working in tandem with a revenge-seeking Carol, whose son had died as a direct result of Alpha’s machinations.

Yet, what did come as a surprise is the fact that he genuinely tried to stop this all from coming to pass. Though Alpha has done horrible things, he still tries to sympathize with her by revealing the way that his pain at the loss of his wife had driven him to become a dreadful person bent on revenge. Alpha refuses to be deterred in her course of action as she intends to kill her daughter Lydia for betraying her, and Negan, protecting Lydia, ultimately kills Alpha and delivers her head to Carol.

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His Whole Thing With Maggie - Season 11, Episode 3 “Hunted”

To say that Maggie and Negan have a complicated relationship is to say that water is wet. After killing her husband Glen right in front of her very eyes while she and the rest of her group were helpless to do anything about it, she vowed revenge on him. When she found out he was being kept in a cell at Alexandria, she was ready to kill him until she realized that he just wasn’t worth it.

Yet, upon her full-time return to Alexandria, seeing Negan walking around as a free man infuriated Maggie. Rather than keeping her distance, she chose to take him along with her on the most dangerous missions, hoping he would eventually die while helping the town. Negan clocks this and leaves her to die, but he later saves her. Though he openly tells her he wishes he’d have killed her along with Glen, the two offer comfort to one another later when they are forced to walk among the undead. Maggie is the person where Negan’s wild card status flares up the absolute most.

He Cared About the Saviors - Season 7, Episode 4 “Service”

Negan’s crew followed his every command, making him seem like a dictator. Yet, there were moments when we saw behind the mask. Though he had no illusions when it came to what the Saviors were about, he also genuinely formed bonds with many of them.

Despite their bloodthirsty actions, the Saviors were the largest known group of survivors, and they seemed to admire and respect Negan beyond his status as their leader. As he noted, “We survive. We bring security to others. We bring civilization back to this world. We are the saviors.” Though this may seem a bit deluded considering what audiences saw of the group, the fact is that they had lofty intentions regardless of their wrongdoing, showing an edge of moral complexity even in regard to his violent gang of killers.

He Gave Up Lucille - Season 10, Episode 22 “Here’s Negan”

As noted above, season 10 was a wild ride for our guy. Yet, it didn’t let up with the season’s closing episode. With Maggie back in Alexandria, Carol moves him out of town for his own protection. This leads him to assess his life and what he has left if he leaves the community for good.

What this episode said about Negan’s past is important, but nothing is more vital than what it says about his future. After a night of soul-searching, he takes the bat he has named after his deceased wife out to a field and buries it, effectively saying the farewell he never allowed himself to say before. Apologizing for using the pain he felt from losing her as a justification for so much wrong-doing, he moves back into his old spot in Alexandria, regardless of Maggie’s hatred of him.

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