The question is finally answered in The Walking Dead: Dead City episode 3, "People Are A Resource." Feeling in a more talkative mood after a few days plodding around Manhattan with Maggie, Negan explains that, following The Walking Dead's series finale, he and Annie moved north toward New Babylon. Once there, a horrific assault on Annie inevitably resulted in Negan exacting revenge on the quintet of men involved, making him an outlaw on the run from New Babylon's marshals. This ultimately prompted Negan to send Annie and their child, now confirmed as a son named Joshua, to an entirely different state.

Why Negan Left His Family (But Still Looks After Ginny)

While Negan does address the circumstances behind his family's absence in The Walking Dead: Dead City, he neglects to explain precisely why he has not yet followed Annie and Joshua to Missouri. Indeed, Negan's decision is even more confusing when considering Ginny - the child Negan adopted after abandoning his actual family. Taking a practical mindset, Negan may have separated from Annie and his son to avoid them being caught in New Babylon's firing line. These post-apocalyptic sheriffs are far from scrupulous about honoring their own rules, but are only interested in Negan. By not following his family, Negan is sparing them a life on the run.

Based on Negan's characterization over the past 5 seasons of The Walking Dead, his self-imposed isolation from Annie and Joshua may also be guilt-driven. As well as potentially feeling like he could have done more to stop the initial incident, Negan's act of retribution then created further danger by bringing New Babylon's marshals to his door. Rightly or wrongly - and consciously or otherwise - Negan perhaps believes his family are safer without him.

Adopting Ginny certainly confuses matters - no doubt little Joshua would feel a little perturbed by his absent father taking a completely different child under his wing. There is clearly more to come from Negan and Ginny in The Walking Dead: Dead City, but Jeffrey Dean Morgan's character perhaps views Ginny as a redemptive road back to Annie and Joshua. If he can protect her and prove himself as a surrogate father, he can return to his old family with his head held high.

Dead City's Negan Story Makes His Walking Dead Ending More Tragic

Hearing the deeply upsetting truth of why Negan split from his family completely changes his ending from The Walking Dead's final episode. Although Jeffrey Dean Morgan did not physically appear during The Walking Dead season 11's post-time skip final sequence, his voice was heard narrating a letter written to Judith. Although Negan's letter proved light on details, the tone was hopeful, and clearly implied the former villain found peace. The package also contained Judith's com, which Negan returned in a symbolic gesture to confirm he found a place in the world.

Apparently not, as the new information revealed by The Walking Dead: Dead City episode 3 completely contradicts the more optimistic ending of The Walking Dead season 11. What was supposed to be Negan's version of a happy ending has turned into a nightmare that makes his decision to swap Alexandria and the Commonwealth for New Babylon look hasty in hindsight. One might also argue that Negan has reneged on promises made in The Walking Dead's final episodes. Having committed himself to the pregnant Annie, Negan affirmed he would always do right by his wife and unborn child.

While Negan had no control over the abhorrent attack his wife experienced in New Babylon, sending Annie and Joshua away and then breaking his promise to follow them is the antithesis of the pledges he made back in The Walking Dead season 11. With the gift of hindsight, not only does Negan's series finale optimism look misplaced thanks to The Walking Dead: Dead City, his growth as a character can be called into question. Negan seemingly handed Judith's com back a few years too early.

The Walking Dead: Dead City continues Sunday on AMC.