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Captain Anthony - Douglass’s first master and probably his father. Anthony is the clerk for Colonel Lloyd, managing Lloyd’s surrounding plantations and the overseers of those plantations. Anthony is a cruel man who takes pleasure in whipping his slaves, especially Douglass’s Aunt Hester. He is called “Captain” because he once piloted ships up the Chesapeake Bay.
Hugh Auld - Thomas Auld’s brother and Douglass’s occasional master. Hugh lives in Baltimore with his wife, Sophia. Thomas and Lucretia Auld allow Hugh to borrow Douglass as a servant for Hugh’s son, Thomas. Hugh is well aware that whites maintain power over blacks by depriving them of education, and he unwittingly enlightens Douglass in this matter. Hugh is not as cruel as his brother Thomas, but he becomes harsher due to a drinking habit in his later years. Hugh seems to suffer some consciousness that slavery and the law’s treatment of blacks are inhumane, but he does not allow this consciousness to interfere with his exercising power over Douglass.