On Spy Wednesday, the Church compels us to look at Judas Iscariot, one of the most painful figures in the Gospel.
Judas was one of the Twelve. He heard the same preaching, saw the same miracles, was intimate with Christ, and still gave him over. That is why his story belongs to every age. It warns us that proximity to holy things does not save a man. God’s grace must be received and responded to with wholeheartedness.
Pope Benedict XVI said that Judas is “a figure belonging to the group of those whom Jesus had chosen as strict companions and collaborators” and that “the possibilities to pervert the human heart are truly many” (General Audience, Oct. 18, 2006). That observation helps us understand Spy Wednesday well. Judas is an insider, close and trusted. He holds the common purse. John says he kept it badly, since “he was a thief, and as he had the money box he used to take what was put into it” (John 12:6).
Great betrayals often grow from smaller infidelities that were tolerated for a long time. Judas did not wake up in one sudden hour as a traitor in full form. Sin had been working in him already. St. Luke writes, “Then Satan entered into Judas called Iscariot, who was of the number of the twelve” (22:3). St. John says, “The devil had already put it into the heart of Judas Iscariot, Simon’s son, to betray him” (13:2). Later, after the morsel, “Satan entered into him” (v. 27). Scripture therefore gives us a grim picture. Judas acts freely and culpably, yet dark spiritual forces also press upon his heart.
“Woe to that man . . .”
What does Jesus mean when he says, “Woe to that man by whom the Son of man is betrayed. It would be better for that man if he had never been born” (Matt. 26:24)?
Those are dreadful words. They reveal the horror of Judas’s deed and the terrible danger into which he placed his soul. Yet the Church has never “canonized” Judas into hell, so to speak. Benedict taught us caution here: “Even though he went to hang himself, it is not up to us to judge his gesture, substituting ourselves for the infinitely merciful and just God.” That is the Catholic path: Christ’s warning is fully serious, but we ought to be careful about human judgment of Judas’s final state.
So would it really have been better for Judas never to have been born? Jesus himself says so, and his words are forceful. They express the ruinous gravity of definitive rebellion against God. They teach us that damnation is real, and they also expose the ugliness of betrayal from within friendship. Psalm 41:9, which Jesus applies to himself, says, “Even my bosom friend in whom I trusted, who ate of my bread, has lifted his heel against me.” This is a betrayal that cuts the heart.
And yet, in another sense, Christ’s saying is a warning word and a dreadful unveiling. Matthew says Judas “repented” in the sense of remorse and said, “I have sinned in betraying innocent blood” (27:3-4). Benedict draws a vital distinction here: “After his fall Peter repented and received pardon and grace. Judas also repented; his repentance degenerated into desperation and thus became self-destructive.” In his book Jesus of Nazareth: Holy Week, Benedict adds, “His remorse turns into despair. Now he sees only himself and his darkness; he no longer sees the light of Jesus.” That is the decisive tragedy. Judas sinned grievously, and then he despaired of the mercy that could have saved him.
Peter also betrayed Jesus, but he ran back toward the Lord. Judas spiraled deeper into himself. That difference matters greatly for Spy Wednesday. A Christian falls either toward Christ or away from him. There is no other option.
He Gave It to Judas
The next question is equally important: how could the apostles be surprised about the betrayer if Jesus said it would be the one who dipped in the dish with him?
The answer lies in the Passover structure. Shared dipping into the common dish would have been a normal part of the supper. The gesture was not a dramatic public condemnation in the way modern readers often imagine. The dipping of the “morsel” in John 13:26, the sop, refers to a customary Passover action of intimacy within the meal that everyone at the meal does repeatedly. Since all at table would have dipped bread or bitter herbs, the sign did not publicly identify Judas for everyone present.
Benedict explains in Jesus of Nazareth that John, writing later, clarifies that the others still did not grasp it. He writes, “We must assume that John retrospectively attributed a clarity to the Lord’s answer that it lacked at the time for those present.” John himself tells us that “no one at table knew why he said this to him” when Jesus told Judas, “What you are going to do, do quickly” (13:28). Some thought Judas was going to buy festival needs or give something to the poor, “because Judas had the money box.” So the Gospel itself answers the question. Jesus gave a sign, John understood it fully only later, and the group in that moment were confused.
That confusion also reveals something tender and sad. The apostles do not instantly point fingers. They ask, “Is it I, Lord?” (Matt. 26:22). There is self-suspicion instead of accusation. This is because each man knew his own weakness. Judas alone says, “Is it I, Rabbi?” and Jesus replies, “You have said so” (v. 25). Even there, Christ deals with him personally, almost secretly, still leaving room for him to turn back.
With a Kiss
Why did Judas need a kiss in Gethsemane if Jesus had been teaching openly in the temple for days?
Several reasons fit the Gospel record. First, Judas had arranged the signal for a nighttime arrest in a garden. Imagine the scene: a dark garden, under pressure, in darkness, with a crowd and armed men present. That prearranged sign removed the potential for confusion. Second, the authorities wanted to seize Jesus “in the absence of the multitude” (Luke 22:6); public arrest in daylight in Jerusalem during the feast would inevitably stir unrest. Third, Judas’s kiss makes the betrayal more terrible precisely because it twists a sign of affection of a disciple into an instrument of treachery toward his rabbi.
Jesus had indeed taught openly. He says, “Day after day I sat in the temple teaching, and you did not seize me” (Matt. 26:55). Even so, the arresting party came at night, and Judas identified him. More deeply, the kiss exposes the moral essence of his betrayal. Sin often comes dressed in veiled tenderness. Luke gives Christ’s piercing response: “Judas, would you betray the Son of man with a kiss?” (22:48).
This is why Spy Wednesday is a lesson for the everyman. Judas’s story warns us against greed, against divided-hearted discipleship, against spiritual presumption, and against despair after sin. Benedict says, “Jesus respects our freedom” and also “awaits our openness to repentance and conversion; he is rich in mercy and forgiveness” (General Audience). That is the core lesson.
So on Spy Wednesday, the Church invites us to examine ourselves. Where have I played with smaller sins? Where have I resisted God’s grace of conversion? Where have I hidden under religious piety while my heart drifted? And if I have sinned deeply, will I run toward mercy or spiral into the darkness of self-accusation without hope?
John closes the scene chillingly: “So, after receiving the morsel, he immediately went out; and it was night” (John 13:30). That line describes the state of Judas’s soul as well as the hour. Judas went out from the Upper Room into the Jerusalem night, and he also stepped farther from the Light of the World into the night of his own betrayal. Spy Wednesday is a day where the Church exhorts us to cling close to that light, lest we are ensnared by the darkness of sin.