PC: In The Poor Sumbitch, the judge never got into his car, he just stood on the courthouse steps. Tried waiting 5 minutes, nothing. Reloaded checkpoint, nothing. Aborted mission and tried again, nothing. Quit out of the game and tried again, nothing, he just stood there.
Finally pulled out my gun and shot him there, but then I got all kinds of weird messages. Instead of the usual "Escape", it told me "Cops witnessed crime", then "Lose the cops", then the objective unselected itself and just showed "Open the map to select an objective". Finally got to the edge of the escape zone, which was way bigger than usual, and ended it though.