Grieve for Judas
…do not become downcast, and do not become gloomy when you hear that the Master was betrayed. Instead, groan and cry out not because Jesus was betrayed, but because Judas betrayed Him.
Sermons on the Life of Christ, by St John Chrysostom (Translation and introduction by Robert G. T. Edwards)
Through this betrayal, the whole world was saved; through this betrayal, Judas ruined his soul. It is for this, for Judas, that we should groan and cry. This is how John opens this sermon, preached on Holy (Maundy) Thursday!
…while Jesus who was betrayed sits at the right hand of the Father in heaven, Judas who betrayed Him is now in Hades, enduring inexorable and eternal punishment.
Do not grieve for the persecuted, because they will be blessed. We read this in the Beatitudes, among many other places.
Matthew 5: 10 Blessed are those who are persecuted for righteousness’ sake, for theirs is the kingdom of heaven.
11 Blessed are you when they revile and persecute you, and say all kinds of evil against you falsely for My sake. 12 Rejoice and be exceedingly glad, for great is your reward in heaven, for so they persecuted the prophets who were before you.
Jesus understood just what it was that Judas was prepared to do:
John 13: 21 When Jesus had said these things, He was troubled in spirit, and testified and said, “Most assuredly, I say to you, one of you will betray Me.”
John understands this not as Jesus being troubled regarding His fate, but troubled out of pity for Judas. We are to mourn those who do evil, not for those who suffer evil. It is an overpowering statement for me. If I have in view only this world, then it is an impossible statement. But this is not (or should not) be the view of one who lives in and for the Kingdom. God’s wrath will come to the persecutors, and to the uttermost:
1 Thessalonians 2: 14(b) For you also suffered the same things from your own countrymen, just as they did from the Judeans, 15 who killed both the Lord Jesus and their own prophets, and have persecuted us; and they do not please God and are contrary to all men, 16 forbidding us to speak to the Gentiles that they may be saved, so as always to fill up the measure of their sins; but wrath has come upon them to the uttermost.
Consider the many trouble spots in the world today, with each of us having a clear idea of which side is the persecuted and which the persecutor. The persecuted will receive the Kingdom; the persecutors will receive everlasting death. Yet, for which do I mourn? For which should I mourn? The answer to both questions is not the same for me; this only shows how far I am from this teaching and understanding.
Do you see that it is right to grieve and mourn most of all for those who do evil?
No, I don’t. Well…I didn’t. But it sure is a lot to ask. Obviously not possible without plenty of help from the Holy Spirit.
In any case, as John teaches it, Jesus was disturbed and did not want Judas to act shamelessly. This is how great Jesus’s compassion was for those who would persecute Him (we see the same when He is on the Cross). In any case, Judas did not receive exhortation or counsel; he gained nothing from Jesus’ longsuffering.
Conclusion
Do you see how suffering evil has a reward and a prize – the kingdom of heaven?
At the same time, doing evil brings punishment. Therefore, do not be angry at our enemies. Instead, have mercy on them; cry and grieve for them. If we prepare our souls truly for this, we will be able to properly pray for them, thus attracting help for them from above.
For Christ did not advise these things only for the sake of your enemies, but also for the sake of us who forgive them their sins. For when you let go of anger toward your enemy, you both receive and give something greater.
I know we are called to love our enemies. But there is something in the way John puts it in this sermon (of which I have only covered the first part in this post) that weighs very heavily on me.

I agree, these teachings are profound and challenging to say the least but I am also constantly haunted by such a way of life. Deep down I know it’s right. It’s repeated by so many of the Fathers and the Saints one way or another. One of “radical” (at the root) forgiveness and love. Hebrews 10:32-39 offers a view (and fruit) to this way of life I think. As you say, it can only be lived by loving Jesus and His offer of Paradise more and loving others so much you desire them to join you in Christ.
The Catholic mystic Caryll Houselander’s vision has been helpful to me. To see an entombed Christ in those who do not know Him. To see Christ in everyone. His incarnation changed the course of the world.
“I saw too the reverence that everyone must have for a sinner; instead of condoning his [or her] sin, which is in reality [their] utmost sorrow, one must comfort Christ who is suffering in [them]. And this reverence must be paid even to those sinners whose souls seem to be dead, because it is Christ, who is the life of the soul, who is dead in them; they are His tombs, and Christ in the tomb is potentially the risen Christ. . . .”