Major spoilers below for anyone who hasn't watched the midseason premiere for The Walking Dead.
Of all the Walking Dead characters that should be fine with being out and about in nature, away from any known systems of authority, it would be Negan. Which made me think the midseason premiere might allow him to go balls-out wacky for a while by taking him outside his Alexandria cell at a point when Michonne and others were away. Instead, showrunner Angela Kang & Co. delivered another episode that smartly utilized Jeffrey Dean Morgan's somber contemplation over Negan's Savior-babble.
Just to throw it out there for those who didn't read the comics, a similar situation went down where Negan had a chance to make an escape, but chose to remain inside his cell as a sign of faith. That sign was for Rick to notice in the comics, though, and Negan made sure that Rick was fully aware of what went down. Rick, of course, made his mega-exit from the TV show in the first half of Season 9, and is set to return for a series of standalone features.
As such, it seemed possible that The Walking Dead would remix Negan's live-action story in a way that allowed him to truly break free from his cell and his bedpan, possibly to stumble upon the Whisperers, and possible to go in a completely new direction. I guess he did try to do that, if only for a short while.
First, he had to actually get outside of Alexandria's walls without drawing any unwanted attention, and with some kind of device that would help him find true north easier. For emotional purposes, he immediately checked Judith's room, where he found her engraved directional compass. Naturally, Judith caught him.
Instead of taking him down or throwing him back in his cell (metaphorically), Judith listened to his genuine and heartfelt and kinda gloomy appeal for why everyone might be better off with him gone. Taking it all to heart, Judith actually let him go, which is when things got even more introspective for the formerly tyrannical Negan.
Not that Negan was a stranger to living a rough life before much of the Saviors' ranks got destroyed (i.e. murdered to bits), but this was the first time in presumably a long time that he was out truly on his own, without a backwardly doting community to return to. As well, it was the first time he was freely in an open environment in something like seven years.
Having that cushy cell life meant that Negan got a little rusty in the "taking out walkers" department. It also wasn't quite as fun for him to mercilessly treat walkers like monstrous animals. By the time he made it back to the Sanctuary and witnessed the destruction and desolation that had persisted there since he'd been imprisoned. It all came to a head when he discovered one of his former acolytes as a walker trapped in an office.
In the end, Negan decided not to continue life as a free man, and instead chose to return to Alexandria, almost getting himself shot by Judith in the process. This could all obviously be some sort of a ruse, but this Negan is definitely a changed man from the one that tried to kill Rick in the Season 8 finale. He even traveled back to the haunted lands where he murdered Abraham and Glenn, finding little solace there.
Negan hadn't really popped up much in the first half of Season 9 outside of a conversation here and there, and it was indeed showrunner Angela Kang's intention to limit his imprisoned appearances early on. Here's how she'd explained it to me when I spoke to her ahead of Season 9's winter finale.
I just felt that for the, for the way that the particular story was going this season, that less was more, you know? Negan definitely has his moments to shine, and he's got more coming up, but it was a conscious decision, just from a storytelling perspective of wanting to show where everybody was at in the aftermath of that war. And it felt more powerful to kind of focus on the people who were not in the prison cell, while also giving us an insight into Negan.
Is Negan truly rehabilitated and repentant of his past sins? Or will having that taste of freedom grow into something more in the near future? Also, are Luke and Alden doomed? I can't wait to find out.