At some point in August's life, he got into police work and became Sleepy Hollow's sheriff. August was a father to a boy named Joseph, whom he had a close bond to. Sometime after, August caught Abbie stealing from a pharmacy. Instead of immediately arresting her and taking her to prison, he took her to a diner and gave her a chance to decide whether or not she was going to make better decisions. When Abbie made the choice to better herself, he would occupy her by making her alphabetize his files. August introduced Abbie to Joseph, and would allow her to babysit him. Over the years, August made plans with Joseph, but his time would be consumed by helping Abbie train to become a cop. On the side of his police work, August evaluated mysterious and supernatural cases around Sleepy Hollow, even