Negan is living that free life on The Walking Dead now that he escaped Alexandria. But he's not flying solo as previews show that Negan will have a traveling companion in the form of Brandon on The Walking Dead. Brandon has appeared in Season 10 as the person who oversees Negan's farm work at Alexandria. While not much else is known about Brandon (at least on the TV series), his choice of traveling companion could majorly cost him.
In the trailer for the fifth episode of Season 10, Brandon is shown with Negan outside of the community. "You're fast. Took me forever to catch up," Brandon says with a smile. From this preview, it sure seems that Brandon may have been the one to release Negan from his jail cell after the death of Margo. But The Walking Dead previews usually can't be trusted (just look at that Ezekiel and Michonne kiss) and Brandon's character is already pretty different from his comic one. Yet, his story may just catch up with the one in the graphic novels by Robert Kirkman now that Negan is free — which is exciting for Negan, but not great for Brandon.
Skybound, the company behind The Walking Dead comics, wrote how Brandon in the comics was indeed the person responsible for breaking Negan out of jail. Yet, Negan killed him before heading into Whisperers territory. Negan murdered the young man because Brandon had wanted to expose Rick's plan of attacking the Whisperers to Alpha and have the two leaders kill each other. The circumstances surrounding how Brandon and Negan end up trekking through the woods together on the TV series are a mystery right now, but the show has changed this character significantly, so his fate could be different too.
Brandon in the graphic novels is the son of Tammy Rose and Morton Rose, the Hilltop blacksmith. In the TV series, Morton has been replaced by Earl Sutton and his son Ken died back in Season 9's "A New Beginning." Comic Brandon's hatred for Rick Grimes stems from the leader not waging war with the Whisperers when his mother Tammy was killed by them. Tammy Rose on the show was killed by the Whisperers too, but this death wouldn't have directly affected TV show Brandon since Tammy wasn't his mother. So his motivation for helping Negan isn't clear.
Brandon is somewhat of a villain in the comics, so Negan killing him there isn't the most tragic event. The personality of Blaine Kern III's Brandon on the show hasn't been revealed yet, so perhaps he's not as cruel as his comic counterpart. Yet, following Brandon's death, Negan infiltrates the Whisperers' camp and gets to know Alpha. So even if he isn't that bad of a guy, viewers may want Brandon dead due to what it could lead to for Negan.
In an interview with Entertainment Weekly after Negan's escape, showrunner Angela Kang wouldn't say how the former Savior ruler got free. But she did say, "We're going to have some fun with Negan, so we'll really get to see [Jeffrey Dean Morgan] doing his thing. I don't want to give too much away there, but there's some of my favorite stuff with him in the next episode."
No matter how Brandon on the TV show connects to Brandon in the comics, Kang's tease means that his involvement with Negan should lead to one of Morgan's more thrilling episodes in ages. Unfortunately for Brandon though, Negan's storyline becoming more interesting may come at the price of his life.