Walking Dead fans are all too familiar with Negan's (Jeffrey Dean Morgan) story, both the good and the bad. His origin story, if you will, was told in the season 10 bonus episode, "Here's Negan." He is then introduced as the leader of the Saviors in season 6 and begins his path to redemption after he is jailed for life in the season 8 finale. Dead City's second season sees the return to his old ways, but one key moment reveals that he is no longer truly a villain.
Walking Dead viewers witnessed all of Negan's brutality and manipulation before seeing the tragic circumstances that led him to that point. His backstory was told in the episode "Here's Negan," which is based on the same-titled standalone issue of The Walking Dead comic. Despite the tragic loss of his wife Lucille (Hilarie Burton-Morgan), nothing excused his behavior after that event.

Negan gathered a large group of followers, known as the Saviors, of which he reigned supreme. They followed his every command and even stated, "I am Negan" when asked who they were. When he was bested by Rick Grimes (Andrew Lincoln) and his group, Negan was given a life sentence and held in the jail at Alexandria.
After this point he did everything he could to redeem himself, which he did in the eyes of some. But the return of Maggie Rhee (Lauren Cohan), wife of Glenn (Steven Yeun), who Negan brutally killed, threw a wrench in his redemption plan as she wouldn't allow his past to be forgotten. By the end of TWD series, Negan would take his wife Annie (Medina Senghore) and their son Joshua away from the communities.
Negan - The Walking Dead: Dead City season 2

When the story caught up with Negan in season 1 of Dead City, he was a wanted man. Defending his wife's honor, Negan killed several important men from New Babylon. He sent his wife and child away to keep them safe. This led to him being reunited with Maggie, whose son, Hershel (Logan Kim), had been abducted by one of Negan's former Saviors.
After being betrayed by Maggie, Negan found himself captive of his old friend, the Croat (Željko Ivanek), and a ruthless woman known as the Dama (Lisa Emery). As leaders of gangs in post-apocalyptic Manhattan, the duo blackmail Negan into joining their ranks in the battle for control of the island. They threaten Hershel and Negan's family, who were located and being brought to the Dama.

In the second season, Negan is seen leading the group and welding a new "shocking" version of his favorite weapon, a barbed wire wrapped baseball bat named Lucille. At first glance, it appears he is thriving in his new role, but there are signs that he is only doing what needs done to keep his family and Hershel from harm.

This is most evident in the second episode of the season, "Another Shitty Lesson." When New Babylon attempts to bring its first wave of its army to Manhattan, via boat, the gangs have other plans and attack them before they make landfall. As Negan directs where and when to bomb, he notices Hershel is among the group on the boat. He halts bombing to allow the young man to escape in a lifeboat. This act doesn't go unnoticed by the Croat, who notifies the Dama of Negan's actions. To punish Negan, she kills Victor (Logan Schmucker), a man Negan befriended.

Negan will always carry the guilt of killing Glenn and has tried to make amends by protecting Hershel. The young man is on his own destructive path, which was revealed when he lit a signal fire to notify the Croat that New Babylon was headed to the island. It is likely that Negan will have to come to the boy's aid once again before the season concludes.
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