On Monday morning Douglass was up early, half hoping that he would be permitted to resume his work without punishment. Covey was astir betimes, too, and had laid aside his Sunday mildness of manner. His first business was to carry out his fixed purpose of whipping the young runaway. In the meantime Fred had likewise fully decided upon a course of action. He was ready to submit to any kind of work, however hard or unreasonable, but determined to defend himself against any attempt at another flogging. In the cold passion that took possession of him, the slave-boy became utterly reckless of consequences, reasoning to himself that the limit of suffering at the hands of this relentless slave-breaker had already been reached. He was resolved to fight and did fight. He began his morning work in peace, obeying promptly every order from his master, and while he was in the act of going up to the stable-loft for the purpose of pitching down some hay, he was caught and thrown by Covey, in an attempt to get a slip knot about his legs. Douglass flew at Covey's throat recklessly, hurled his antagonist to the ground, and held him firmly. Blood followed the nails of the infuriated young slave. He scarcely knew how to account for his fighting strength, and his daredevil spirit so dumfounded the master that he gaspingly said: "Are you going to resist me, you young scoundrel?" "Yes, sir," was the quick reply.
Finding himself baffled, Covey called for assistance. His cousin Hughes came to aid him, but as he was attempting to put a noose over the unruly slave's foot, Douglass promptly gave him a blow in the stomach which at once put him out of the combat and he fled. After Hughes had been disabled, Covey called on first one and then another of his slaves, but each refused to assist him. Finding himself fairly outdone by his angry antagonist, Covey quit; with the discreet remark: "Now, you young scoundrel, you go to work; I would not have whipped you half so hard if you had not resisted."
Douglass had thus won his first victory, and was never again threatened or flogged by his master. The effect of this encounter, as far as he himself was concerned, was to increase his self-respect, and to give him more courage for the future. He said that, "when a slave cannot be flogged, he is more than half free." To the other slaves he became a hero, and Covey was not anxious to advertise his complete failure to break in this "unruly nigger." It speaks well for the natural dignity and good sense of young Douglass that he neither boasted of his triumph nor did anything rash as a consequence of it, as might have been expected from a boy of his age and spirit.…
[A carefully planned attempt at escape failed dismally, but he remained undaunted.]
Ever since the first trouble with Auld, he had been pushing his plans to redeem his pledge to himself that he would run away on Monday, September 3, 1838. These were anxious days, and many small details had to be mastered. He must carefully avoid anything in manner or word which could excite the slightest suspicion. He had to test the fidelity of a number of free colored people whose aid, in secret ways, was very essential to him. Who these persons were has never been revealed, and, in fact, it was not until many years after emancipation that Mr. Douglass disclosed to the public how he succeeded in making his daring escape. "Murder itself," he says, "was not more severely and surely punished in the State of Maryland than aiding and abetting the escape of a slave."
Young Douglass's flight had no outward semblance of dramatic incident or thrilling episode, and yet, as he modestly says, "the courage that could risk betrayal and the bravery which was ready to encounter death, if need be, in pursuit of freedom, were features in the undertaking. My success was due to address rather than to courage, to good luck rather than bravery. My means of escape were provided by the very means which were making laws to hold and bind me more securely to slavery."
By the laws of the State of Maryland, every free colored person was required to have what were called "free papers," which must be renewed frequently, and, of course, a fee was always charged for renewal. They contained a full and minute description of the holder, for the purpose of identification. This device, in some measure, defeated itself, since more than one man could be found to answer the general description; hence many slaves could get away by impersonating the real owners of these passes, which were returned by mail after the borrowers had made good their escape. To use these papers in this manner was hazardous both for the fugitives and for the lenders. Not every freeman was willing to put in jeopardy his own liberty that another might be free. It was, however, often done, and the confidence that it necessitated was seldom betrayed. Douglass had not many friends among the free colored people in Baltimore who resembled him sufficiently to make it safe for him to use their papers. Fortunately, however, he had one who owned a "sailor's protection," a document describing the holder and certifying to the fact that he was a "free American sailor." This "protection" did not describe its bearer very accurately. But it called for a man very much darker than himself, and a close examination would have betrayed him at the start. In the face of all these conditions young Douglass Was relying upon something besides a dubious written passport. This something was his desperate courage. He had learned to act the part of a freeman so well that no one suspected him of being a slave. He had early acquired the habit of studying human nature. As he grew to understand men, he no longer dreaded them. No one knew better than he the kind of human nature that he had to deal with in this perilous undertaking. He knew the speech, manner, and behavior that would excite suspicion; hence he avoided asking for a ticket at the railway station, because this would subject him to examination. He so managed that just as the train started he jumped on, his bag being thrown after him by some one in waiting. He knew that scrutiny of him in a crowded car en route would be less exacting than at the station. He had borrowed a sailor's shirt, tarpaulin, cap, and black cravat, tied in true sailor fashion, and he acted the part of an "old salt" so perfectly that he excited no suspicion. When the conductor came to collect his fare and inspected his "free papers," Douglass, in the most natural manner, said that he had none, but promptly showed his "sailor's protection," which the railway official merely glanced at and passed on without further question. Twice on the trip he thought he was detected. Once when his car stood opposite a south-bound train, Douglass observed a well-known citizen of Baltimore, who knew him well, sitting where he could see him distinctly. At another time, while still in Maryland, he was noticed by a man who had met him frequently at the shipyards. In neither of these cases, however, was he interfered with or molested. When he got into the free State of Pennsylvania, he felt more joy than he dared express. He had by his cool temerity and address passed every sentinel undetected, and no slave, to his knowledge, he afterward said, ever got away from bondage on so narrow a margin of safety.