9.16: The Walking Dead - Storm

So there was two time jumps and Kang confirmed that Whisperer's had gone south for the Winter.

The Walking Dead has always kept its linear timeline a little blurry for fans. Carl's age often threw viewers off in regards to how long Rick and company had been in the apocalypse. Time jumps of undisclosed lengths have been carried out on several occasions. As it turns out, the Season Nine finale might have snuck in a couple more following the unforgettable "pike" deaths of 10 characters.

"So, from Henry's death to the snow I imagine it's several months," The Walking Dead showrunner Angela Kang told INSIDER." We're kind of tracking it through Rosita's pregnancy." Rosita was visibly pregnant in the Season Nine finale episode after only having recently realized she was pregnant in the episode which aired one week prior.

"She was probably barely pregnant at the time of the death," Kang said." And, then, we jumped forward to [where] she's quite a bit pregnant. Between that and seeing the Whisperers, there's probably been a passage of a bit of time, but really what we wanted to imply was [that the Whisperers] are a migratory group. And, so, they may have gone South for the winter. They're not even in the same space, but there probably has been a little bit of time that's passed. But, we're not talking about a matter of a huge time jump."

Then came another possible time jump. Before King Ezekiel was seen talking to Judith over the radio (and receiving an alarming transmission from a mysterious new group), the episode cut from the snow-covered Alexandria sequences to a sunny day in the woods with the Whisperers. The trees were green. There was no snow. It seems as though another few months have passed heading into Season 10.

"The timelines will become more clear as we jump into season 10 and the stories start to converge again," Kang promises.
'The Walking Dead' Snuck in Another Time Jump With Season 9 Finale
 
Well, that was as clear as mud, but then, I have always had a problem with understanding their time jumps in any case.

To be honest, now that we know for sure that there was timejumps, the whole trek was a waste of time. Yet, they played it like it was all connected.
 
I think sometimes the showrunners realize they have to explain some points after the fact because they don't make sense in the show itself. The show never uses labels saying place or time at the start of scenes. Time and location jumps shouldn't be a mystery. Though to be fair I think they avoided some time travel/teleportation issues that were in the previous series of Game Of Thrones. And people mostly forgave those.
 

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