Henson finally arrived with these slaves at the farm of his master's brother, five miles south of the Ohio and fifteen miles above the Yellow Banks, on the Big Blackfords' Creek in Davies County, Kentucky, April, 1825. Here the situation as to food, shelter and general comforts was a little better than in Maryland. He served on this plantation as superintendent and having here among more liberal white people the opportunity for religious instruction, he developed into a successful preacher, recognized by the Conference of the Methodist Episcopal Church.

There he remained waiting for his master three years. Unable to persuade his wife to move to Kentucky, however, his master decided to abandon the idea and sent an agent to bring upon those slaves another heartrending scene of the auction block, though Henson himself was exempted. Henson saw with deepest grief the agony which he recollected in his own mother and which he now unfortunately said in the persons with whom he had long been associated. He could not, therefore, refrain from experiencing the bitterest feeling of hatred of the system and its promoters. He furthermore lamented as never before his agency in bringing the poor creatures hither, if such had to be the end of the expedition. Freedom then became the all-absorbing purpose that filled his soul. He said that he stood ready to pray, toil, dissemble, plot like a fox and fight like a tiger.

A new light dawned upon the dark pathway of Josiah Henson, however, in 1828. A Methodist preacher, an anti-slavery white man, talked with Henson one day confidentially about securing freedom. He thereupon suggested to Henson to obtain his employer's consent to visit his old master in Maryland that he might connect with friends in Ohio along the way and obtain the sum necessary to purchase himself. His employer readily consented and with the required pass and a letter of recommendation from his Methodist friend to a preacher in Cincinnati, Henson obtained contributions to the amount of one hundred and sixty dollars on arriving in that city, where he preached to several congregations. He then proceeded to Chillicothe where the annual Methodist Conference was in session, his kind friend accompanying him. With the aid of the influence and exertions of his coworker Henson was again successful. He then purchased a suit of comfortable clothes and an excellent horse, with which he traveled leisurely from town to town, preaching and soliciting as he went. He succeeded so well that when he arrived at his old home in Maryland, he was much better equipped than his master. This striking difference and the delay of Henson along the way from September to Christmas caused his master to be somewhat angry. Moreover, as his master had lost most of his slaves and other property in Maryland, he was anxious to have Henson as a faithful worker to retrieve his losses; but this changed man would hardly subserve such a purpose.

The conditions which he observed around him were so much worse than what he had for some time been accustomed to and so changed was the environment because of the departure or death of friends and relatives during his absence that Henson resolved to become free. He then consulted the brother of his master's wife, then a business man in Washington, whom he had often befriended years before and who was angry with Henson's master because the latter had defrauded him out of certain property. This friend, therefore, gladly took up with Henson's master the question of giving the slave an opportunity to purchase himself. He carefully explained to the master that Henson had some money and could purchase himself and that if, in consideration of the valuable services he had rendered, the master refused to do so, Henson would become free by escaping to Canada. The master agreed then to give him his manumission papers for four hundred and fifty dollars, of which three hundred and fifty dollars was to be in cash and the remainder in Henson's note. Henson's money and horse enabled him to pay the cash at once. But his master was to work a trick on him. He did not receive his manumission papers until March 3, 1827, and when Henson started for Kentucky his master induced him to let him send his manumission papers to his brother in Kentucky where Henson was returning, telling him that some ruffian might take the document from him on the way. In returning to Kentucky Henson was arrested several times as a fugitive, but upon always insisting on being carried before a magistrate he was released. He had no trouble after reaching Wheeling, from which he proceeded on a boat to Davies County, Kentucky.

Arriving at the Kentucky home, he was informed that the master had misrepresented the facts as to his purchase. He had written his brother that Henson had agreed to pay one thousand dollars for himself, the balance-of the six hundred and fifty dollars to be paid in Kentucky. As the only evidence he had, had been sent to his master's brother, it was impossible for him to make a case against him in court. Things went on in uncertainty for about a year. Then came a complaint from his master in Maryland, saying that he wanted money and expressing the hope that Henson would soon pay the next installment.

Soon thereafter Henson received orders to go with Amos Riley carrying a cargo to New Orleans. This suggestion was enough. He contrived to have his manumission papers sewed up in his clothing prior to his departure on the flat boat for New Orleans. He knew what awaited him and his mind rapidly developed into a sort of smoldering volcano of pent-up feeling which at one time all but impelled him to murder his white betrayers. Blinded by passion and stung by madness, Henson resolved to kill his four companions, to take what money they had, then to scuttle the craft and escape to the North. One dark night within a few days' sail of New Orleans it seemed that the opportune hour had come. Henson was alone on the deck and Riley and the hands were asleep. He crept down noiselessly, secured an ax, entered the cabin, and looking by aid of the dim light, his eye fell first on Riley. Henson felt the blade of the ax and raised it to strike the first blow when suddenly the thought came to him, "What! Commit murder, and you a Christian?" His religious feeling and belief in the wonderful providence of God prevented him.

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