Kenny flashback. My version.

EPISODE 1 PART ONE. THE TIES THAT BIND.

1st flashback. A year after season 2 ends.
Kenny and Clem have found a little place to live not far from Wellington, perhaps a farmhouse or something. They survive by scavenging the land, occasionally, getting supplies from people heading to Wellington or from Wellington in return for providing a safe place to sleep, or directions to Wellington. One day, a group comes upon Kenny and Clem, and Kenny sensing danger, tells Clem to hide with AJ. This group takes all of their supplies and beats Kenny up so badly he ends up with a broken leg. Kenny sends Clem away to find something to bind his leg.

EPISODE 1 PART TWO THE TIES THAT BIND.

2nd flashback.

While searching for stuff to bind Kenny's leg, Clem comes across a small group of walkers and gets cornered. She hides in an old caravan and comes across AVA, who mentions the New Frontier and offers Clem a place.

EPISODE 2

3rd Flashback.

Clem returns to bind Kenny's leg and the two reminisce about their time together, remembering Lee, Kat, Duck, Lilly and Luke, even Jane. However, Clem becomes concerned with Kenny talking about Duck and Kat, even Lee, like they're still alive. He even seems confused somewhat, with him asking if they're heading back to the motor inn now as they head off toward Wellington. When Clem raises her concern, he brushes it off as him being tired.

EPISODE 3

4th Flashback.

Clem and Kenny reach Wellington to find it has been destroyed, overrun by Zombies. They figure out that the group that broke Kenny's leg must've done this to Wellington. After looking for supplies and finding a car, Clem mentions that she met a woman who mentioned a group down in Richmond who would be more than happy for them to join them. So they take the car and head south. Kenny once again mentioning his family like they were still alive.

5th Flashback.

Kenny teaches Clem how to drive as he can't because his leg is broken. While driving south they come across a herd of walkers. They drive through, have a couple of near misses, but eventually reach Richmond and the New Frontier.

EPISODE 4

6th and final flashback. A few months before A New Frontier begins.

Clem and Kenny are now the age they were in the TTG flashback. Clem is a little bit rebellious, because sometimes teenagers are. We spend time with David and learn through Clementine what happened after he became separated from Javier. Clem has doubts about New Frontier because of the way they seem to be leaning toward, what with the brands, which get introduced this flashback. Ava is the leader of The New Frontier, and likes Clem and wants her to get the branding too.

When she heads back to where she and Kenny are staying to ask his advice, or voice her concerns, she discovers that Kenny has passed away in his sleep, peacefully. (Let him survive and die from natural causes, being happy for a while)
Clem gets the brand and then tries to leave after rethinking her situation, or witnessing the New Frontier using Kenny's reanimated corpse for their Walker farm. She attempts to take AJ but David stops her. He lets her leave but refuses to let her take AJ with her, as AJ would be in danger outside the protection of the NEW FRONTIER.

Not the best scenario, but the best I could come up with off the top of my head.

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