Douglass does not begin to detest his master, and regard his enslavers as the "most wicked of men," until he reads "The Columbian Orator." What is it about this text and its content that really disturbs him, apart from the idea that he might not be able

From the text:

They gave tongue to interesting thoughts of my own soul, which had frequently flashed through my mind, and died away for want of utterance. The moral which I gained from the dialogue was the power of truth over the conscience of even a slaveholder. What I got from Sheridan was a bold denunciation of slavery, and a powerful vindication of human rights. The reading of these documents enabled me to utter my thoughts, and to meet the arguments brought forward to sustain slavery; but while they relieved me of one difficulty, they brought on another even more painful than the one of which I was relieved. The more I read, the more I was led to abhor and detest my enslavers.

In essence, what Douglass learned from the text was that Master Auld was right when he warned his wife about education and slavery.... the way that literacy served to make slaves non compliant.