When a judge passes down a sentence it may require mandatory jail time (whether or not the sheriff believes it to be too harsh). Example: The Douglasville 6 were older teens ranging in ages 15-17 who had sex with a 14-year old. She was a willing participant. The young men were sentenced to 10 years in jail and branded sexual predators. Even the sheriff believes this is wrong, but there's nothing he can do. Hell, there's nothing the judge can do because of mandatory sentencing rules.
A judge can also pass down a sentence with specific orders, like he did with Hilton. He ordered that there would be no house arrest or work release. The Sheriff took it upon himself, probably with the heavy influence of the smell of Hilton money, and ignored the order. The problem he created was the inmates, upon hearing about the ordeal and reasons, probably contacted lawyers saying they want the SAME treatment. But because they are not slathered in Hilton cash, won't get it. I could hear the paperwork being filed here on the east coast!
As far as Ann C speaking out, I'm not surprised. She's been out of the spotlight for a while and this was her in. She probably saw that most Americans were happy about Hilton returning to jail and thought the best way to get back into the headlines would be to say the opposite. She's as parasitic as Paris.
The Winkler case wasn't about cold blooded murder, it dealt with domestic abuse and a healthy cup of the crazies. If you want to talk about fairness in our justic system, the tribunal overseeing the gitmo detainees throughout several cases because the prisoners were not 'unlawfully' enemy combatants, which they have to be in order to stand trial. With their cases dismissed, are these prisoners allowed to return to their families? No, they remain in prison, with no writs of habeus corpes (thanks Bush), untill the administration can drum up other charges.