With Douglass and other slave members finally coming up with a successful plan, they had to figure out how to deal with a problem. If they do get stopped, what do they do? Douglass figured out that he would right passes, allowing him and his other slave members to travel up north for the holidays. He figured that they would need them when they finally get on land, because they are more likely to be stopped on land then in the water. They feared that if they would get caught, that they would be imprisoned if they didn’t have those passes. “Frederick, what are you young?” asked one of the slaves. “I am writing passes for us, so we won’t get in trouble if we do get caught for escaping”. Said Douglass. “ Great idea, Frederick!” said the slave. Douglass then handed the slave one of the passes that he had finished with. “These look exactly like the actual passes!” he said.
Douglass was really excited to start on his plan. He worked very hard for days and days, with little to no sleep about it. One day however, all that that hard work had changed. He was eating breakfast one morning when Mr. Freeland said there were two people at the door who were white, and wanted to see him. Once he got to the door, the men seized him and tied him together. Somehow, they figured out what Douglass was planning, so he took out his pass and managed to put it in a fire that was close by. They got ahold of the other slaves that were planning to escape with douglass as well, but one of them tried to fight back, and it did not end well. There were not convicted of running away yet, sense Douglass got his pass in the fire.
After this incident, Douglass and some of his other slave friends that were planning to escape, were going to be taken to jail. The constables would soon take them to ST Michael, where they were taken into prison. A lot of the other slaves still had their passes, however, and they didn't want to keep them for the constables to see, or they could possibly get more jail time. Douglass was very sad while in the prison, and that just a few days before he went to the jail, he was full of hope and confidence. He had learned a valuable lesson, however. It will all work out in the end, he thought. Now he had no confidence and thought that the possibility to gain freedom was impossible. Soon later, he was taken out of jail by Mr. Auld, his owner. “ Why did you take me out of the prison, sir?” said Douglass. “Because, your going to Baltimore to work for my brother” he said. Douglass was very relieved and grateful for Mr. Auld, especially when he hasn’t treated him the best in the past when he lives there before working for Mr. Freeland.