Earlier quoted context omitted.
No, but if the court orders it and he refuses, can that not be construed as contempt of court? People definitely go to jail for that.
That's criminal, not civil court. Civil court works on fiscal, property to mitigate damage. If he is found to breach contract, a court could order seizure of assets (cash or property). There could be punitive damages assessed too, if his actions are seen as purposefully malign.
You can have criminal contempt in a civil case and criminal contempt in a civil case. The rules vary by state but in PA it’s civil contempt is used to force people to comply where criminal is punishment for disobedience.