Caleb Gillen (born 1790) was the son of Virginia planter Charles Gillen. An idealist, young Caleb had become entranced with the laws and political system of the Federated Commonwealths, so much so that he even began educating the family's house-slave, Jeremiah. Caleb went to Portsmouth and became an apprentice of attorney Zachary Hayes. In the meantime, an outbreak of diphtheria killed many of the Gillens' sims. Jeremiah was put into the fields. After a day, he fled to Portsmouth himself, and began working for another lawyer, Alfred Douglas.