Douglas experiences many transformative events in his life. One of the event he describes as a turning point, however, is when Douglas was sent to Edward Covey, a “first rate hand at breaking young negroes.” (Douglas, p.159)This particular period of uncertainty begins with the death of Captain Anthony, who, Douglass notes, had remained his master "in fact, and in law," though he had become "in form the slave of Master Hugh" (p. 136). Captain Anthony's death necessitates a division of his human "property," and soon afterwards, Hugh Auld sends Douglass to work at his brother Thomas Auld's plantation, on Maryland's Eastern shore. During the nine months Douglas has lived with Thomas Auld, he got several sever whippings, “without any visible improvement in [Douglas’] character, or [his] conduct.” (Douglas, p.157) This also shows how “stubborn” he was which indicates that he would not change in any way and submits himself. When Douglas is put with a nearly impossible task, and fails to do so, Covey punishes Douglass harshly. But Douglass does not intend to be broken either, and his year with Covey culminates in a violent fistfight with the overseer. Douglas is strong and he does not give up. In the end, Covey gives up the fight. Douglas says that he had to be victorious, “because [Douglas’] aim had not been to injure [Covey], but prevent his injuring [him].” (Douglas, p.186) This brutal struggle, Douglass recalls, "rekindled in my breast the smouldering embers of liberty (. . .) and revived a sense of my own manhood" (p. 187). From this incident on, Douglas is hardly physically punished and every attempt of brutality is unsuccessful. This incident also made Douglas a man who is “not afraid to die.” (Douglas, p.187) Douglass emphasizes his victory over Covey as a turning point in the narrative: "This spirit made me a freeman in fact, while I remained a slave in form" (p. 187). Douglas was only sixteen of age.