Then how about Marie Therese Metoyer? She started life as a slave, but ended up owning her own plantation. She was eventually able to buy all of her children out of slavery. According to church records, she owned 12 slaves at the time of her death, but local tradition has it that she was freeing them as well. It's also established that she ran her plantation with no slaves and only help from her sons for many years.

So she's a former slave, a liberator of slaves, and a plantation owner and owner of slaves all in one. Would having her on a bill be in poor taste? (Granted, there are probably more prominent persons who should be on a bill before her.)

(I once dated one of her descendants.)