''The Boondocks'' is a dark comedy about a middle class African American family named the Freemans (Robert Freeman, Huey Freeman and Riley Freeman) that lives in Woodcrest, a predominantly white neighborhood. The perspective offered by this mixture of cultures, lifestyles, social classes, stereotypes, viewpoints and racialized identities provides for much of the series' satire, comedy, and conflict.
'''Who is he? What MEHs has he crossed?'''
Wuncler is a loan shark who preys on fiancially vulnerable families only to get them further indebt. Eventually making them sign themselves into slavery making them work as actual slaves in a theme park called "Freedom Land" in a twisted reinactment of the 19th century plantation. He has done this to dozens, possibly hundreds of families.
We see the families working as slaves suffering various manners of abuse and torture. Children are put in potato sacks and pushed off hills, they are then chained in boxes and splashed with water guns, put in torture racks, etc. It is also heavily implied that he stabbed one of his slaves to death in a fit of rage. In the climax, we see the full extent of his brutality when he tries to slice off Huey's feet to make a public example out of him (Huey is only ten years old, btw).
None shown. He has a son and grandfather but he never interacts with them onscreen so we have no idea what his relationship with them is like.
Yes. Unlike many others on the show he is presented as a realistic business predator. Who's violent tendencies are nightmare fuel in-universe.
I am not going to lie. The heinous standard is high. Alot of evil acts are played for comedy. There is a rapist named the Booty Warrior who gets to sent to jail for raping a man and is implied to had raped others. There is this evil business woman who kills two of her employees for not being "EVIL" enough. There are Stinkmeaner and his evil crew, the Hateocracy who have some nasty attempted murders.
There is even his own father, Wuncler Sr. who exploits child labor and blew up a building with several people in it to try to kill one man. However I would say, Wuncler II is worse since he has mass slavery/torture on his rapsheet which Wuncler Sr. doesn't really get up to, nor due do any of the other characters, although Ruckus did act as the Freemans overseer.