The Highwaymen are a rough and aggressive, but not an unreasonable group of 22 survivors that stalk roads and prey upon travelers, robbing them and extorting communities that use "their" roads. Despite being thieves and extortionists, the Highwaymen prefer to conduct their business peacefully, normally sending letters with a list of demands rather trying to obtain supplies through brute force. Though they have been known to use brute force, such as ambushing Jerry and beating him up, they don't appear to resort to killing the living unless absolutely necessary. They appear to be educated as their demand letter is grammatically correct which is pointed out as a notable fact by the residents of the Kingdom. Their motivation simply appears to be a need for supplies to survive rather than other more sinister motivations like many antagonistic groups such as the Saviors or the Whisperers.
After Carol and Ezekiel negotiate with them, the Highwaymen put their outlaw ways aside, at least for the time being, and start protecting the roads leading to the Kingdom in exchange for having access to the fair where they can sell their stolen supplies. The Highwaymen are shown to have begun clearing the roads of walkers and even setting up patrols in the area for possible enemies, taking their new jobs seriously. Along with trading at the fair, the group is promised the chance to watch a movie for the first time since the apocalypse began. When their job increases, Ozzy, possibly jokingly, asks for more movies in repayment for their services rather than something more unreasonable or trying to use the situation to get the Highwaymen a better deal.
Though they have access to an array of guns, the Highwaymen appear to rely mainly on melee weapons much like the other communities. Such weapons are known to include a pipe wrench wielded by their leader Ozzy.
Nothing is known about the lives of individual members of the Highwaymen before or as the outbreak began.
At some point, the Highwaymen started camping near roads and extorting other survivors for their supplies. They recently moved to an area near the Kingdom, possibly enabled by Carol killing Jed and his group of rogue Saviors whose territory it used to be.
The Highwaymen ambush a group from the Kingdom led by Jerry taking their supplies and sending back a demand letter with them for a ransom to allow the trade delegation to come. Though the Kingdom soldiers originally plan to ambush the Highwaymen, Carol points out the lack of unnecessary violence towards Jerry's group and instead suggests negotiating with them. During a meeting with Ozzy and his men, Carol offers a deal where the Highwaymen, who admit to desperately needing supplies as well, can join the trade fair in exchange for working for the Kingdom by keeping the roads safe. As a standoff begins, the group's interest is drawn when Carol asks when the last time they've seen a movie was.
Having ultimately accepted Carol's deal, a group of Highwaymen led by Ozzy agree to escort the delegation from the Hilltop. They arrive just in time to help Tara's group fight off an attacking herd that has nearly overwhelmed them. The Highwaymen then escort the Hilltop group to the Kingdom for the fair.
Working with D.J., Ozzy and Alek clear the road of walkers near the Kingdom. When another group arrives, they reveal the site where Hilde was ambushed. Ozzy reveals that the Highwaymen know of the Whisperers and he promises to have his patrols keep an eye out for them. In return for the extra workload, Ozzy asks, possibly jokingly, for access to more movies for his people.
Ozzy, Alek and D.J.'s undead heads are later found on pikes by Daryl, Carol, Michonne, Yumiko, and Siddiq along with Alpha's other decapitated victims. Addressing the gathered communities, Siddiq reveals that before the end, Ozzy, Alek and D.J. found the other prisoners and gave them a chance to fight back. Fighting together, the prisoners killed several Whisperers before finally being taken down in a heroic last stand.
With Ozzy and Alek's death, the group merged with The Coalition and now live in the various communities that are a part of it.
The Highwaymen members, including Margo, are seen in and around Oceanside doing several tasks such as training and putting out the forest fire.
At an emergency council meeting to discuss the incoming waves of walkers in Alexandria, Margo speaks for the Highwaymen and demands justice, while Gage wants to put the Whisperer's heads on spikes. Siddiq has a panic attack and exits. Daryl reaffirms he saw tens of thousands of walkers in Alpha's herd. Michonne tells everyone instead of retaliating, she and a small group will meet with Alpha at the border to work things out.
Margo and Alfred attends a training session in Alexandria led by Aaron, but watches Gage taunting Lydia with a mask made out of a burlap sack when she approaches the group of soldiers. She laughs alongside Alfred and Gage before telling Lydia to go away. At the Alexandria dining hall, Lydia sits at the table of Margo, Alfred and Gage. She guts a squirrel, in which blood shoots onto Gage's face. As Gage storms away, Alfred brings up Ozzy and Alek's deaths to Margo and questions how they can be okay with Lydia living alongside them. Margo instead tells him not to cause trouble with everyone present.
That night, Margo, Alfred and Gage ambush Lydia by the clotheslines and order her to leave Alexandria. When Lydia refuses, Margo proceeds to beat her and holds her to the ground, ordering Gage to attack her, reminding him of Addy and Rodney's deaths, while Alfred screams that Ozzy was his best friend. When Negan arrives to rescue Lydia, Margo is thrown off of the frightened girl into a wall, accidentally slamming her head against it and dying immediately of severe head trauma to the shock of a horrified Alfred and Gage, who claims they were just trying to scare her. Daryl and the residents arrive to address the situation. Alfred blames Negan for Margo's death but Lydia screams it wasn't his fault. Daryl believes her but orders Negan back to his cell.
Margo is examined by Siddiq, who confirms the nature of her death. A short time later, Margo is buried in a grave. Shortly after, Alfred and Gage are questioned by the Alexandria council on the events that just occurred. They feed the council lies and are in disbelief when the council begins questioning their story, and eventually they are let go.
Alfred and another guard are inside a house helping each other put on their armor before heading out on watch duty. He jokes and brags about how he and his friends attacked Lydia and claims that the Whisperers can barely fight. Moments later, Alfred and the man are murdered by Beta and left to reanimate. He and the guard soon turn and wander Alexandria attacking others before finally being put down.
This list shows the victims the Highwaymen have killed:
- It is possible, though unconfirmed, that this was the group responsible for the disappearances of several Kingdom residents before the events of "Who Are You Now?", since Jed claimed he only found their supplies. If this is the case, it is rather odd that they would just abandon these supplies, but it is possible that they hid them and Jed's group just happened to find them. However, given the group's less violent approach, it is unlikely, since its implied that the missing people are likely dead and the Highwaymen haven't been known to kill humans unless necessary.
- It's suggested in "Chokepoint" that Carol killing Jed's group of rogue Saviors enabled the Highwaymen to take up residence in the area around the Kingdom. However, this can be seen as the more positive outcome. Whereas Jed and the Marauders were staunchly loyal to the Savior ways, the Highwaymen were reasonable and willing to be of aid in exchange for services.
- The Highwaymen are the second group to renounce their antagonistic ways in the same episode they are introduced, the Vatos being the first.
- Thanks to a Facebook post from Valdez Williams who portrayed an unnamed Highwaymen in Season 9, where it shows him back on set as a survivor, it's possible that the Highwaymen may either still be active and/or have merged with the Coalition.
- The tenth season's premiere confirms that they merged with the Coalition. This can be proven with the fact that several Highwaymen, including Margo, are seen in and around Oceanside doing several tasks such as training and putting out the forest fire. In addition, the Highwaymen demand justice from the Whisperers in "Ghosts" for the deaths of Ozzy and Alek in an Alexandria council meeting.