K, so in Lawful Good you got Pope Saint Gregory the Great, kinda self explanatory. He instigated the first large scale mission, created multiple methods of meditation and singing, is a Doctor of the Church, all of it falls in line with being an A+ man who also works within the confines of the law.
Neutral Good you got Pope St. Peter. He was more of a wildcard, he was humble freely admitted to being sinful. He was a bit hit-or-miss with the whole lawful thing, sometimes he cut men’s ears off, other times he had to have an “in depth discussion” with St. Paul cause St. Peter wasn’t comfortable eating the food of Gentiles caues the laws he grew up in prohibited such. Still, good man.
Pope Saint John Paul II lived in a place and time where dozens, if not hundreds of people wanted him dead, and his response was to roll with the punches, pull James Bond stunts to outwit most of their assassination/espionage attempts, and dressed like this
I rest my case
So in Lawful Neutral there we got Pope Benedict XII. Interesting history, there was a practice where, during the first ballot of voting, cardinals would put in a random name to see where their colleagues were leaning and they could discuss further based on the results. Welp, the accidentally all voted for the same guy in 1334. He wasn’t that bad as a Pope, very activist which is why he is Lawful, but Neutral because literally no one thought he’d do it.
Then there’s Pope Leo XI, who is true neutral cause he was in office for 26 days. From what I found, that was the shortest reign and I can’t say much else.
Then in Chaotic Neutral there is Pope John XXI who is responsible for the only discrepancy in naming for Popes I know about. See, he got it in his head that the last Pope to go by John was Pope John XX, but that wasn’t right, last one was Pope John XIX. Pope John XX has never and now will never exist because Pope John XXI just didn’t have time to check the numbering of the last man to carry his desired name!
Now we get into the kinda dark stuff. Pope Innocent III was a Crusader Pope and had some pretty sobering actions that people still debate over today. Nothing really “illegal” but still damaging enough that a few days after he died, he appeared to St. Lutgardis of Aywières (a great Catholic mystic) begging that she and her Sisters pray for him as he was sent to Purgatory for 3 great faults and that should he not have prayers for his and others in Purgatory’s salvation, his time there would last centuries.
Then there’s Pope Benedict IX. He was made Pope three times, sold his papacy once, was the first pope to resign, and had homosexual orgies in the Lateran palace. So uh, yeah, kinda hard to place but the man was definitely not the most moral.
And finally Pope John XII. Leeeet’s see, he ordained a 10-year-old as a bishop, ordained a deacon in a horse stable, was accused of fornicating with his father’s mistress (not the one who may have been his mother, presumably), his own niece, and several widows, and “made the sacred palace into a whorehouse.”, blinded his confessor and then killed him, castrated a subdeacon before also killing him, was “devoted to hunting, hawking, gaming, and wine” more than the papacy, toasted the devil, made friends with Otto I of Germany, then enemies of Holy Roman Emperor Otto I of Germany and ran off with the papal treasury after his attempt to battle Otto’s army to the death didn’t pan out.
Wide Spread Interests 