I'm wondering if there were any such occasions, and what suttas/sutras this is recorded in.
Also if the Buddha gave advice to otherwise evil people besides Angulimala or Devadatta, or possible connections to psychopathy or sociopathy.
Corrupted officials: Dhanañjani Sutta
"What do you think, Dhanañjanin? There is the case where a certain person, for the sake of his wife & children ... his slaves & workers ... his friends & companions ... his kinsmen & relatives ... his guests ... his departed ancestors ... the devatas ... the king, does what is unrighteous, does what is discordant. Then, because of his unrighteous, discordant behavior, hell-wardens drag him off to hell. Would he gain anything by saying, 'I did what is unrighteous, what is discordant, for the sake of the king. Don't [throw] me into hell, hell-wardens!' Or would the king gain anything for him by saying, 'He did what is unrighteous, what is discordant, for our sake. Don't [throw] him into hell, hell-wardens!'?"
Other evil people(demon): Alavaka Sutta