His third master was "vulgar in his habits, unprincipled and cruel in his general deportment and especially addicted to the vice of licentiousness."[2] On his plantation Henson served as water-boy, butler and finally as a field hand, experiencing the usual hardship of the slave. He ate twice a day of cornmeal and salt herring, with a little buttermilk and a few vegetables occasionally. His dress was first a single garment, something like a long shirt reaching to the ankles, later a pair of trousers and a shirt with the addition of a woolen hat once in two or three years and a round jacket or overcoat in the winter time. He slept with ten or a dozen persons in a log hut of a single small room, with no other floor than the trodden earth, and without beds or furniture. In spite of this, however, Henson grew to be a robust lad, who at the age of fifteen could do a man's work. Having too more mental capacity than most slaves, he was regarded as a smart fellow. Hearing remarks like this about himself, Henson became filled with ambition and pride, and aspired to a position of influence among his fellows. At times Henson would toil and induce his fellow slaves to work much harder and longer than required to obtain from their master a kind word or act, but these efforts usually produced no more from their owner than a cold calculation of the value of Josiah to him. When, however, the white overseer of this plantation was discharged for stealing from his employer, Josiah had shown himself so capable that he was made manager of the plantation. In this position his honest management of the estate made him indispensable to his master also as a salesman of produce in the markets of Georgetown and Washington. He had during these years come under the influence of an anti-slavery white man of Georgetown and had become a devout Christian with considerable influence as a preacher among the slaves.