7. Urban VI complained that the victims of his torture did not scream loudly enough
As with Clement V, Urban VI was not elected from within the College of Cardinals. He was selected largely due to the demands of a Roman mob which pressured the conclave to elect a Roman and prevent the papacy from sitting in Avignon. Urban VI was neither Roman nor French, but as a Neapolitan presented an acceptable compromise. After his election the French cardinals and clergy entered into many conspiracies against him throughout his papacy. One of his earliest edicts was that the cardinals were not to accept financial remuneration, and he condemned the luxurious lifestyles of most of the clergy.
Having alienated the French, Urban found himself and his authority challenged by a second pope, elected by the French cardinals with the support of the King of France. Robert of Geneva became Clement VII, and a series of wars over the papacy began in 1387. For Urban the war went badly, and he was at one point confronted by several cardinals who requested that he place himself under their supervision. Urban considered the request an affront, part of a conspiracy against him, and had them arrested and tortured. During the torture he complained to one of his supporters that the victims were not screaming loudly enough to suit him. During his papacy anyone he did not consider loyal was subject to torture followed by execution, including emissaries unfortunate enough to deliver messages from their masters which he deemed threatening.