Nothing is known about Ozzy's life before or as the outbreak began.
At some point following the outbreak, Ozzy became leader of a group of survivors known as "the Highwaymen".
In their base, Ozzy greets Carol, Ezekiel, and Jerry as they enter. He informs them this meeting is for the King alone. They disagree, and Ozzy asks if they have his toll, while his people approach with their weapons drawn. He suggests they use Ezekiel as ransom when suddenly the Kingdom fighters grab his people from behind. Ezekiel draws his sword and says he’s prepared to fight for what they’ve created. He then offers Ozzy a job to clear his roads for him in exchange to access for the Kingdom and the fair. Ozzy laughs in his face and draws Jerry’s sword, telling them they’ll have to do better than that. Carol then asks when the last time they’ve seen a movie and a shocked Ozzy responds, “Seriously?”
Later, on the road, Ozzy and some of the Highwaymen ride up on horses and introduce themselves to Tara and the Hilltop group after helping them to take down a herd. They then escort them to the Kingdom, having accepted Carol's deal.
In the Kingdom, Ozzy walks around with his horse as he passes by Jerry. He then tips his hat and smiles to Carol and Ezekiel, signaling of trust.
Ozzy will appear in this episode.
This list shows the victims Ozzy has killed:
- Numerous counts of zombies and possibly unnamed people
Ozzy and Jerry have a rather poor relationship, since Ozzy and the Highwaymen beat Jerry up and stole his sword. Jerry is in favor of fighting the Highwaymen, and particularly wishes to retrieve his sword. After Ozzy and his men agree to become escorts to the fair, Jerry and Ozzy eye each other down as Ozzy passes by, hinting the two have not mended their relationship as of yet.
Ozzy and Ezekiel have a tense relationship at first, since Ozzy attempted to extort the Kingdom of it's supplies. While Ezekiel wanted to fight the Highwaymen at first, Carol convinced him to negotiate with them. After a tense standoff, a deal was reached, and the Highwaymen agreed to help the Kingdom keep the roads safe. Ozzy can later be seen greeting Ezekiel and Carol in a friendly manner.
Ozzy and Carol have a tense relationship at first, since Ozzy attempted to extort the Kingdom of it's supplies. Nonetheless, Carol wished to negotiate with the Highwaymen instead of simply killing them, which Ezekiel eventually agreed to. It was Carol's offer of letting the Highwaymen see a movie that ultimately made Ozzy relent and agree to help the Kingdom keep the roads safe. Ozzy can later be seen greeting Ezekiel and Carol in a friendly manner.
It can be assumed the two have a positive relationship, since Ozzy and the Highwaymen helped Tara and the other Hilltopers fight off a herd.