The Hilton soap opera

I don't think that the Judge is thinking too clearly here. Let us imagine for a moment that he does order Paris back to jail. Her lawyers will immediately appeal and request release on bond pending appeal. If the court refuses they will take it to the appeals court where the legal issues are sufficiently complicated for them to almost certainly get the lower court ruling suspended. By the time the issue actually came to trial Paris would have served the full sentence and the issue would be moot.

There is a separation of powers issue here. The court is not the executive. Paris would not have received a prison sentence for a probation violation if she wasn't a celebrity. The jail is overcrowded and regularly releases prisoners early in this way.

The Sheriff ultimately answers to the Governor of the state, he is not an agent of the court. The court can hardly expect the Sheriff to take himself into custody.