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When Master Thomas came to town, Douglass inquired if he would hire Douglass out, but the man refused, calling it a "stratagem by which to escape" and encouraged Douglass to remain content with his situation.
Douglass then asked Master Hugh for the same thing two months later, and after some careful thought, Mater Hugh agreed. The deal was that Douglass could find work but pay Master Hugh three dollars a week and cover his own food, room, calking tools, and clothing. This arrangement favored Master Hugh because "it relieved him of the need of looking after me. His money was sure. He received all of the benefits of slaveholding without its evils; while I endured all of the evils of a slave, and suffered all the care and anxiety of a free man.