While brooding over this conundrum, I flipped open the Summa Theologica at random to Part III, Question 47,
Of the Efficient Causes of Christ's Passion, and found the following:
"Bede, likewise, commenting upon the words, 'For they know not what they do,' says 'It is to be observed that He does not pray for them who, understanding Him to be the Son of God, preferred to crucify Him rather than acknowledge Him.'"
Christ only prayed for those who were ignorant of what they were doing.
On the contrary, as St. Thomas would say, would it have been wrong to pray for the conversion of Saul? He was very determined to persecute Christians, much like one of today's Modernist anti-Popes, but at the same time he was ignorant of the true God.
I answer that ( this is fun ), we should not pray for the
forgiveness of those who are persecuting God and the Church while they are yet in that state, while they are acting as persecutors. But we can pray for their
conversion, which, if it comes about, may then lead to their forgiveness.
If Christ neglected to pray for even the conversion of some of his persecutors that is because He could see into their hearts, and knew it would be no use. We cannot do that. However, wasn't it proven that God prays for His persecutors whom He knows beforehand will repent when the Holy Ghost said to Saul, "Saul, Saul, why do you persecute me?" Therefore how much more should we humans, without any knowledge of what goes on in a man's heart, pray for all men to be converted, even the worst? We cannot tell a Saul from a Caiphas.
But what if someone dies in their heresies or errors or unbelief or defiance, with no outward sign of repentance. Would it be wrong to pray for them?
We can only judge by externals. If someone commits ѕυιcιdє, what more is there to say? Can they be buried in hallowed ground, or prayed for as if they have a chance to go to heaven? There's a prayer in the Mass where you can insert the name of the dead faithful -- could you insert the names here of anyone whose faithfulness was in doubt?
The book is closed on the dead. Yes, they might have had a final moment of repentance, but as humans who only see externals, shouldn't our prayers be based on those externals? Isn't this why Catholics used to refuse prayer for dead catechumens who,
as far as we can see are not in the earthly Church, the Church Militant?
Pretty nifty segue, eh? ( Yes, I disagree with the untrustworthy Code of Canon Law 1917 that catechumens should be buried in hallowed ground -- it feels wrong and now I know why ).
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I'm not sure that it is always wrong to pray for someone who dies in a public state of disgrace, boasting of their atheism or the like. Hence all the question marks. I personally would not do it -- it feels like an error of human respect. A ѕυιcιdє should be quickly buried without prayers, as he failed to obtain final perseverance, due to some fault or sin of his, and this can be objectively known by the act itself of ѕυιcιdє.
I suppose, bringing this back to JPII, if there is ANY chance that he converted before death, we can pray for his forgiveness, but only if we make sure to show God that we are only praying for him conditionally IF he repented. Such is my opinion. To know he was a rat-fink who sold out the Church for decades and died gloating over his misdeeds, and to still pray for him, hoping that God forgives him despite all that as some kind of extraordinary act of mercy, strikes me as very bad.
As with the ѕυιcιdє, I personally would not pray for him at all as there are no reasonable grounds to suspect that he ever changed. But I believe it's certainly permissible, even laudable and an act of charity, to pray for the worst heretics while they're alive and have a chance to convert.