I don't judge people. He seemed like a very cool guy who did a lot of good things and also did a few bad things. Who hasn't messed up, who among us is all perfect?
I think you're misguided to say having ██████████████, earning some money, nepotism and gaining power were bad ideas -- as opposed to what, losing your grip on power as the Pope himself and fading into oblivion and falling out of relevance?
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I think girls, money, power and helping friends and family (nepotism) is something I try to do every day; it's my job.
I don't think his crimes are that bad at all because back in those days you probably had to do those bad things to survive and maintain his respect, especially as the Pope.
I think the mistakes an evil Pope could do, which are far worse are these:
1. Ban contraceptives which causes unwanted pregnancies and diseases
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3. Hate homosexuals and help attack them
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6. Forgive criminals for serious sins
7. Again, "Indulgences"
But anyway, what we should be asking is: "what if the Pope was one of us?"