Jussie and the Court of Appeals

How do y’all think this will play out?

I think he loses the appeal, goes back to jail and pays back Chicago the money he owes.

Hypothetically, if he wins the appeal, and gets another trial, do you see this playing out differently?
If he gets a new trial and is found guilty, for a second time, do you think his sentencing will be or could be, more severe?