The Highwaymen

"We're the Highwaymen. We're your escorts to the fair. At your service."

- Ozzy introducing his group to Tara.

The Highwaymen are a group of formerly hostile survivors. They are first introduced in the episode "Chokepoint" of AMC's The Walking Dead.

Overview
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. 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.

Pre-Apocalypse
Nothing is known about the lives of individual members of the Highwaymen before or as the outbreak began.

Post-Apocalypse
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.

"Chokepoint"
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.

"The Calm Before"
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.

Ozzy, Alek and D.J.'s undead heads are later found on pikes by Daryl, Carol, Michonne 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.

Members

 * Ozzy (Leader)
 * Alek
 * At least 11 other members

Killed Victims

 * Numerous counts of zombies and possibly unnamed people
 * Many unnamed Whisperers (Caused and Direct)

Deaths

 * Ozzy (Alive and Zombified)
 * Alek (Alive and Zombified)

Season 9

 * "Chokepoint"
 * "The Calm Before"

Trivia

 * 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.
 * 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 first group to renounce their antagonistic ways in the same episode they are introduced.