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The “Woe to him”, and Unbroken Grace
In our modern Western Christianity, Matthew 26:24 is often weaponised to construct a theology of ultimate damnation:
“The Son of Man indeed goes just as it is written concerning Him, but woe to that man by whom the Son of Man is betrayed! It would have been good for that man if he had not been born.”
For many, this single sentence seems to seal Judas’ fate, painting him as a doomed pawn in a divine tragedy, cast out forever into endless torment. But when we strip away centuries of medieval penal dogmatics and view this moment through the lens of First-Century Jewish idiom and the immediate context of the Gospel narrative, a radically different picture emerges. One, not of ultimate condemnation, but of heartbreak, grief, and scandalously persistent mercy.
A Common Hebrew Idiom, Not a Dogma of Torment
To read “it would have been good for that man if he had not been born” as an explicit proof-text for Eternal Conscious Torment (ECT) is to misread ancient Hebrew literary culture.
In ancient Jewish thought and Rabbinic literature, hyperbolic phrases regarding non-existence were frequently used to express deep sorrow, profound tragedy, or severe shame. These are never used as technical decrees about eternal metaphysical torture in the afterlife.
Job cursed the day of his birth in his agony (Job 3:3)
Ecclesiastes speaks of an untimely birth being better off than a man who experiences deep misery (Ecclesiastes 6:3)
Jeremiah longed to have remained in the womb (Jeremiah 20:14–18)
This was not language defining the afterlife; it was an expression of utter tragedy. Jesus was articulating the unbearable weight of self-inflicted ruin and spiritual grief that Judas would suffer after exchanging Love incarnate for mere silver. The word “woe” (ouai in Greek) is not an authoritative curse or a decree of divine vengeance, it's a heartbroken lament: “Alas, what a tragedy for that man!”
“Drink from It, All of You”: Mercy in the Face of Betrayal
If Jesus intended to cut Judas off from divine grace, His actions just moments later make no sense at all.
A few verses after speaking of this sorrow, Jesus does something extraordinary. He takes bread, blesses it, breaks it, and gives it to His disciples. Then He takes the cup, passes it around the table, and utters words that reframe human history:
“Drink from it, all of you; for this is My blood of the covenant, which is poured out for many for the forgiveness of sins.” - Matthew 26:27–28
Notice that Jesus does not say, “Drink, all of you - except Judas.” He does not dismiss the betrayer from the room before establishing the new covenant. Judas sits at that very table. Judas receives the broken bread. Judas is handed the cup of forgiveness.
Even while knowing the exact nature of Judas’ treason, Jesus extends the physical symbols of His self-giving life and total forgiveness directly into Judas’ hands. Mercy remains present, offered, and unbroken, even in the immediate presence of betrayal.
A Room Full of Deserters
It's easy to isolate Judas as the solitary monster in the room, contrasting him with eleven "steadfast heroes". Yet Jesus knew the truth about every man sitting with Him that night:
“Then Jesus said to them, ‘You will all fall away because of Me this night...’” - Matthew 26:31
Judas handed Jesus over for silver, but all of them turned away and fled. Peter denied Him three times, cursing Him. The rest vanished into the darkness to protect their own skins.
Judas was not a unique anomaly in a group of righteous saints; he was part of a company of broken, fearful human beings who all, in their own way, deserted the Messiah. Yet Jesus broke bread with every single one of them. He offered His life, His blood, and His forgiveness to all of them without distinction.
The Unconquerable Heart of God
The tragedy of Judas was not that God ran out of mercy, or that a line had been crossed beyond which divine love could no longer reach. God’s nature is love, and His mercy is never exhausted by human failure.
Judas’ heartbreak was that he turned inward in self-loathing and despair rather than returning to the Table where grace had already been served to him.
Matthew 26:24 is not proof that God abandons those who fall; it's a sobering reminder of the agony we bring upon ourselves when we turn from love. And yet, standing right beside our deepest betrayals is a Saviour who breaks bread, passes the cup, and invites us - all of us - to drink and be restored.

