Today is traditionally called “Spy Wednesday” because this is the day that Judas Iscariot betrayed our Lord to the Sanhedrin. Judas became a spy for the Enemy. He watched Jesus and the Disciples and waited for the moment to betray them all, and he betrayed the Christ with a kiss.
 
All three Synoptic Gospels include the account, as it is an important moment in the events of the Passion (Mt 26:12-14, Mk 14:10-12, Lk 22:3-6). Each provides a few details that are worth considering.
 
Matthew tells us that Judas betrayed Jesus for 30 pieces of silver, while Luke paints a diabolical picture of the conspiracy to destroy Jesus:
Now the feast of Unleavened Bread, called the Passover, was drawing near, and the chief priests and the scribes were seeking a way to put him to death, for they were afraid of the people. Then Satan entered into Judas, the one surnamed Iscariot, who was counted among the Twelve, and he went to the chief priests and temple guards to discuss a plan for handing him over to them. They were pleased and agreed to pay him money. He accepted their offer and sought a favorable opportunity to hand him over to them in the absence of a crowd.
 
Why Did He Do It?
 
Luke’s account demands the question that Christians have asked since the Passion: Why did Judas betray Jesus? After all, he was one of the Twelve (Mt 26:14, 47; Mk 14:10, 20; Jn 6:71; cf. Lk 22:3), and Acts also references that Judas was among the Apostles, as Peter declares, “he was numbered among us and allotted his share in this ministry” (Acts 1:17).
And yet, there are constant warning signs in this disciple. He opposed the anointing of Jesus at Bethany, for example, asking, “Why was this oil not sold for three hundred days’ wages and given to the poor?” John adds, “He said this not because he cared about the poor but because he was a thief and held the money bag and used to steal the contributions” (Jn 12:4-6). 
 
The motivation for Judas in his active betrayal of Jesus remains a mystery, and scholars, saints and theologians have long pondered it. Perhaps he sought to have Jesus brought before the authorities in order to force events forward to have Jesus proclaimed as the Messiah. Possibly, he wanted to bring Jesus into a situation in which he is forced to prove himself as the Messiah. And, of course, both Luke and John suggest that Satan had entered into Judas, and he was delivered firmly into the darkness.
 
One aspect of Judas that is especially significant is the way that Judas refers to Jesus only as “Rabbi” (Mt. 26:25). He saw him as a teacher and seems never to have developed a belief in Jesus as the Christ. His faith was still shallow. He journeyed with Jesus, heard him teach and saw the miracles. And still his faith was meager. Long before he went to the Sanhedrin, Judas was betraying Jesus in little ways. 
 
 
The Betrayer and Penitent
 
The account of the betrayal is connected intimately with the reaction of Judas when the enormity of his crime became apparent. He tries to bring the money back to the chief priests and elders, crying out, “I have sinned in betraying innocent blood” (Mt 27: 3-4). Matthew has already given the alarming declaration of Jesus, “The Son of Man indeed goes, as it is written of him, but 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” (Mt. 26:24).
 
Despairing of forgiveness, overcome by his guilt and unable to see even at the end that he could repent and turn in faith to God’s loving mercy, Judas hangs himself.
 
The priests know the blood they bought with the money. Matthew adds, “The chief priests gathered up the money, but said, 'It is not lawful to deposit this in the temple treasury, for it is the price of blood.' After consultation, they used it to buy the potter’s field as a burial place for foreigners. That is why that field even today is called the Field of Blood” (27:3-10).
 
A reading of the Passion narratives provides a stark contrast with Peter who denied Christ three times but repented and found God’s mercy.  
 
In a 2006 General Audience, Pope Benedict XVI meditated on Judas, and he reminded all of us of the power of that mercy. 
 
For us it is an invitation to always remember what St. Benedict says at the end of the fundamental Chapter Five of his "Rule": "Never despair of God's mercy". In fact, God "is greater than our hearts", as St. John says (I Jn 3:20).
 
Let us remember two things. The first: Jesus respects our freedom. The second: Jesus awaits our openness to repentance and conversion; he is rich in mercy and forgiveness.
 
Besides, when we think of the negative role Judas played we must consider it according to the lofty ways in which God leads events. His betrayal led to the death of Jesus, who transformed this tremendous torment into a space of salvific love by consigning himself to the Father (cf. Gal 2:20; Eph 5:2, 25).
 
The Greek word “to betray” is the version of a Greek word that means “to cosign.” Sometimes the subject is even God in person: it was he who for love "cosigned" Jesus for all of us (Rm 8:32). In his mysterious salvific plan, God assumes Judas' inexcusable gesture as the occasion for the total gift of the Son for the redemption of the world.
 
 
Hard questions
 
In Matthew 26, Judas is confronted about his imminent betrayal of the Master. His reply is classic for those exposed of their crimes and sins:  “Surely it is not I, Rabbi?”
 
The Gospel narrative asks all of us hard questions. We see ourselves as far removed from Judas Iscariot, but if we are honest, are we not more like him than we would care to admit? Do we not betray our Lord in so many little ways? Is our faith strong enough? Do we see him as the Christ, the Son of God, or do we impose our own view upon him, trying to make him into our own image and desires? Do we test him rather than trust him? 
 
In the end are we also spies for the darkness?