The Highwaymen are a rough and aggressive, but not an unreasonable group of 13 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, it is unknown what becomes of the remaining Highwaymen though the group presumably remains active.
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.
- ↑ https://www.facebook.com/photo.php?fbid=917275451951206&set=a.133437853668307&type=3&theater&comment_id=917404128605005¬if_t=feedback_reaction_generic¬if_id=1564262126893951
|TV Series Groups|
|Bank Robbers • Rick's Group • The Vatos Gang • The Living • Michonne's Group • The Prisoners • Woodbury Army • Tyreese Williams' Group • The Governor's Militia • Abraham's Group • The Claimers • The Wolves • The Saviors • Oceanside • The Scavengers • The Militia • CRM • Georgie's Group • Magna's Group • The Whisperers • The Highwaymen • Jocelyn's Group • The Coalition|