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A slaveholder with whom Douglass lived for a short time following his time with Covey. Freeland was an "educated southern gentleman" (57) and did not possess the evil traits of most slaveholders. He did not profess to be religious and had traits of humanity and kindness. He fed his slaves enough and Douglass considered him the best master he had.
Known for being a consummate "slave-breaker," Covey was a poor man and a farm renter. Thomas Auld sent Douglass to him in order to avail him of his insolence. Covey was a hard worker and was thus intensely critical of his slaves; he spied on them and tolerated no laziness or perceived autonomy. He professed to be religious, but was a hypocrite and a blasphemer. Douglass was never more broken and despairing than while at Covey's farm, but eventually proved his mettle by fighting back against him and not allowing himself to be whipped.