Lauren Ridloff has only just returned to The Walking Dead, but is she already hurtling toward a grim ending in the Commonwealth? To the shock of absolutely no one, politicians and public officials fared better than most when the zombie outbreak started. We've encountered Deanna Monroe in the main show, Elizabeth Kublek in Walking Dead: World Beyond, and Senator Vasquez in Fear The Walking Dead, but the latest post-apocalyptic politician is by far the most prominent. Currently leading the Commonwealth, Pamela Milton belongs to a world-renowned political dynasty similar to the Kennedy family. Most survivors are already aware of Pamela from before The Walking Dead's timeline, which certainly speaks to her fame and reputation.
One The Walking Dead character who knows Pamela Milton extremely well is Connie. After spending most of season 10 battling Deviants with her brothers and sisters, Connie made a triumphant return in The Walking Dead season 11, part 1. Arriving home to find Alexandria looking somewhat worse for wear, Connie is one of many survivors who accept Lance Hornsby's offer to join the Commonwealth. Now back in a civilized society, Connie resumes her pre-outbreak career of journalism, snooping out the Commonwealth's hottest stories - fancy dress competition winners, the hottest masquerade ball outfits, over-sized pumpkins, etc. Back in the day, however, Connie's typewriter was knocking out more hard-hitting scoops... and her reporting resumé includes none other than Pamela Milton herself.
Connie tells Daryl about the time she interviewed Pamela Milton before the zombie apocalypse. A conversation during the masquerade ball implies Connie might've even covered Pamela's father while he was occupying the White House. But by far the most important detail of Connie's journalistic past comes from Kelly, who subtly drops a bombshell - Connie's reporting was responsible for getting Pamela's uncle kicked out of Congress. The Walking Dead offers nothing further on what Mr. Milton might've done, nor what role Connie played in exposing it. Whatever might've gone down, The Walking Dead must've mentioned it for a reason - and that can only spell bad news for Connie.
In a dangerously subtle moment of foreshadowing, Pamela greets Connie at The Walking Dead season 11's Halloween ball with, "Lovely to see you again," before turning to Kelly and uttering, "Nice to meet you." This exchange discretely confirms Pamela remembers exactly who Connie is. Is that because of her stellar journalistic endeavors? Possibly. More likely, it's thanks to Connie disgracing Pam's uncle and dragging the Milton name through the dirt. There's still plenty viewers don't know about the Milton clan; even so, The Walking Dead has made two family qualities plain - they love a spot of nepotism, and they perceive themselves above the law.
That should have Connie looking over her shoulder while inside the Commonwealth's walls. Maybe the Miltons couldn't get back at Connie before the apocalypse, but Pamela makes the rules now, and the Commonwealth is her domain. If any ill will remains from unclegate, Pamela may have designs for revenge in The Walking Dead season 11, and the zombie apocalypse is the perfect place to serve it up, offering plenty of ways to die, with no one to tell the Miltons what they can't do.
Could this be what finally drives a wedge between the Commonwealth and Alexandria? We know Maggie, for whatever reason, refused Lance's offer of Commonwealth citizenship. We know Commonwealth soldiers will eventually descend aggressively upon Maggie's Hilltop community, and many suspect Daryl Dixon will switch sides after joining Mercer's military. Daryl and Connie are obviously (very, very slowly) building toward a romance. If Pamela Milton was to hurt Connie, that would explain the shocking conflict and Daryl twist we saw in The Walking Dead season 11's six-month flashforward.