Mr. Covey treated his slaves unbearably. Douglass would have to remove his clothing and get whipped until the blood ran down his back. One day Douglass decided to fight back against Covey's brutal beatings, and shocked Covey to the point that he never whipped Douglass ever again. Douglass had lost his longing to learn and escape, but after his fight with Covey, Douglass regained his spirit and determination to be free. After living through the torment with Covey, Douglass is sold to William Freeland, who was the kindest master compared to all the others. Douglass started to educate the other slaves and planned an escape, everything was going well until Douglass's plan to escape was discovered. He was put in jail and sent back to Baltimore to live with the Aulds and learn the trade of ship caulking. Douglass became a caulker and was eventually allowed to hire out his own time. While working and making his own money, he would had to give all of his earnings to Mr. Auld. Douglass decided to keep some money on the side for himself, but at the end of the day, he would tell his master that that was the entire amount he made. Douglass saved enough money to escape to New York City. He found himself in an unfamiliar city, without shelter, food, money, or friends. He was surrounded by people, but afraid to speak with anyone for fear that they will turn him in. A man by the name of David Ruggles, and abolitionist and journalist, takes Douglass in and tells him he should go to New Bedford, Massachusetts, to find work as a caulker. While in New York Douglass got married to Anna Murray, a free black woman from Baltimore; then they moved to New Bedford, Massachusetts, where Douglass was eventually hired as a lecturer for the American Anti-Slavery Society.