- "I'm sorry, Mr. Grimes. I was distracted. I wasn't as diligent as I should have been... It won't happen again."
- —Benjamin telling Rick that he won't mess up his job again.[src]
Little to nothing is known about him before the apocalypse or after the events of All Out War.
Benjamin was chosen for a job as keeping the main route to Hilltop Colony safe and 'clean' for five miles. However, he lets Rick Grimes down, and Rick is almost killed by roamers. Benjamin rides up on horseback to investigate the noise and to make sure Rick is okay. He apologizes after realizing his mistake and that he almost got "Mr. Grimes" and his son killed. Rick briefly hits him with his cane and tells him off for his actions, asking for his name and his home community. Rick angrily tells Benjamin how important his job is, and that if he messes up again it could mean greater losses for the communities. Rick also mentions that people kill for a job like this, which implies it is a hard job to get, and that Benjamin will be reported ("the first and last time") for his negligence. He is also warned that, if he messes up again, he will be reassigned.
This list shows the victims Benjamin has killed:
- Numerous counts of zombies.