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By 1835 Douglass had decided to try and seek freedom again. He felt that he needed to do this as he fast approached manhood. His friends wanted to participate in the attempt to escape as well, but all were aware of the immense obstacles they faced. They were often appalled when they considered the difficult road before them: starvation, drowning, scorpions, wild beasts, snakes, being captured and shot dead on the spot, etc. However, Douglass preferred death to "hopeless bondage".
Sandy gave the plan up but encouraged his friends. Those planning to flee included Douglass, Henry Harris, John Harris, Charles Roberts, and Henry Bailey (the latter two being Douglass's uncles).the plan included getting a canoe that belonged to Freeland's father-in-law and paddling directly up the Chesapeake Bay. The water route would be safer than land. Douglass wrote documents called protections for the slaves, saying that William Hamilton had given them permission to travel to Baltimore for the Easter holidays.
No man wavered in his commitment to the escape, though all were afraid. Douglass felt the weight of the success or failure of the mission on his shoulders since he had created this plan. That morning when he went out to the field to work, he suddenly had a profound feeling of despair, and turned to Sandy and said, "We are betrayed!"
After work in the field ended, Douglass headed back up to the house and saw four white men and two colored men. The colored men were tied up. The men told Douglass that they learned he had been in a "scrape" and that he was to be examined before his master and would be set free if they could not find information on him. John was tied up, and eventually Henry was too after some scuffle. Douglass tossed his forged protection into the fire when no one was looking. Before they are taken to jail, Freeland's mother gives biscuits to Henry and John, and yells at Douglass for putting thoughts of escape into their heads.
In a moment to themselves, the slaves agree not to tell anyone anything and to feign ignorance. They were more concerned with being separated from each other than anything else. Henry, John, and Douglass were placed in a jail cell together, apart from Charles and Henry Bailey. A few slave traders flocked to look at them, and Douglass commented that "a band of pirates never looked more like their father, the devil."
Eventually Henry and John were taken home but Douglass was left alone in the cell. He knew this separation was a final one. He was disconsolate that only days earlier he had been filled with hope, and now he was imprisoned. Thankfully, however, his fate was decided – he was to be sent back to Baltimore to live with Master Hugh and his wife.
Douglass was hired out to Master Gardner on Fell's Point to learn how to calk (waterproof). This was not easy because Gardner was in a rush and all men were to do what they knew best. This put about seventy-five men as Douglass's bosses, and he had a lot of tasks. He would have continued there longer if not for the fight he had with four white apprentices.
These white men began to feel that slaves were competing with them for jobs, and decided to put a stop to it. They began verbally abusing Douglass and refusing to work, sometimes even hitting him. Douglass always fought back when they were separate, but one day all four of them came upon him and beat him terribly.
Douglass came home and told Master Hugh; to his surprise, both Master Hugh and his wife were furious at the harm done to Douglass. His mistress fussed over him and helped take care of his wounds. Master Hugh tried to take care of it but realized that no white man would testify on Douglass's behalf. No one was courageous enough to do so even if they sympathized with the slave; it was not considered safe or proper to express positive feelings towards slaves or abolitionism.
Master Hugh did not want Douglass to return to Gardner, so he was sent to the shipyard of Master Price to finally learn calking. He became quite skilled and began earning high wages. The fact that he had to turn all of these over to Master Hugh upset him. In his leisure time he began to think about freedom again. This was a trend: whenever he had more time and had better conditions, he thought of freedom more and was less contented. When he was busier or faced harsher circumstances, he did not make plans to escape. It was clear that slaveholders found it "necessary to darken his moral and mental vision, and, as far as possible, annihilate the power of reason."