How long did Negan spend behind bars in Alexandria’s jail before his escape in The Walking Dead season 10 episode 4? Alexandria’s prison cell was built by Morgan Jones with his own fair hands back in The Walking Dead’s sixth season as a means of dealing with enemy groups without having to slaughter them, as Rick Grimes tended to do a little too often. The cell briefly housed Dwight in season 7 after he defected from the Saviors but found a more permanent resident in Negan, who was sentenced to life by Rick and Michonne after the Saviors were defeated in the season 8 finale.
Negan didn’t rest on his laurels while incarcerated at the Alexandria Pop-Up Penitentiary. Not only did Negan grow an impressive beard, but he also took up meditation at Father Gabriel’s behest and became something of a mentor to Judith Grimes, who came to him for advice and help with her math homework. Later, after Negan saved Judith from certain death when a freezing blizzard hit Alexandria, he was allowed time out of his cell under supervision and The Walking Dead season 10 episode 1 found him happily tending to a tomato patch.
In The Walking Dead season 10 episode 4 "Silence The Whispers," however, it looked like Negan’s prisoner privileges might be revoked after he rescued Lydia from getting beaten up by Gage, Alfred and Margo, and accidentally killed Margo in the process. Negan soon found himself locked back up in his cell with many Alexandria townsfolk calling for his execution, but his captivity didn’t last long. By the end of The Walking Dead season 10 episode 4 Negan had escaped but how long was he imprisoned before his jailbreak?
Negan was first jailed at the end of The Walking Dead season 8 around two years into the zombie apocalypse. He was incarcerated for approximately one-and-a-half years while Rick was still in charge and then The Walking Dead had its big six-year time jump in season 9 following Rick’s apparent death. That means Negan was behind bars for around seven-and-a-half years in total before he made his escape.
It soon transpired Negan hadn’t simply escaped from jail in The Walking Dead season 10 episode 4 but was actually released by Carol on the condition he infiltrates the Whisperers and kill Alpha. Negan successfully completed that mission but subsequent episodes of The Walking Dead proved the act of offing Alpha hasn’t entirely redeemed him – especially in the eyes of the recently returned Maggie Rhee.