Louis I, Duke of Orléans
During his youth, he had been close to Philip II, Duke of Burgundy, and they were comrades in arms on several occasions. This proximity to Burgundy was largely a result of his father's moving away from the French court, the court to which the Lorrainer dukes had neared in the past century and a half as they withdrew from the Holy Roman Empire, within which their duchy was still technically a vassal state. Charles was defiant of Louis I, Duke of Orléans, who had supported the citizens of Neufchâteau against his father and the Emperor Wenceslaus when the latter was accused by his subjects of weakness. Wenceslaus was deposed in 1400 and replaced by Rupert III, Count Palatine of the Rhine, Charles' father-in-law.