Jesus said to His disciples, "You know that in two days' time it will be Passover, and the Son of Man will be handed over to be crucified."-- Matthew 26:1-5; 14-16.
Then the chief priests and the elders of the people assembled in the palace of the high priest, who was called Caiaphas, and they consulted together to arrest Jesus by treachery and put Him to death. But they said, "Not during the festival, that there may not be a riot among the people."
Then one of the Twelve, who was called Judas Iscariot, went to the chief priests and said, "What are you willing to give me if I hand him over to you?" They paid him thirty pieces of silver, and from that moment, he began to look out for an opportunity to betray Him.
Judas and his motivations have always fascinated me -- perhaps that was the influence in my youth of Jesus Christ Superstar (original concept album), which focuses on him a lot (I hated the movie, with it's Manson family style hippies, not the story/music, even if I can see now the theological errors and perhaps impiety of the JCS story).
I tend to be somewhat sympathetic towards him, but in the end cannot complain too much about his fate because that is the fate he chose of his own free will.
I tend to shy away from the view that he was always an evil villain and scoundrel to the core -- after all, Jesus chose him, and Jesus would not choose someone merely to use him, to be a pawn, He chose him to a follower, not a betrayer. I tend to think away from the view that Judas betrayed Jesus knowing and believing Him to be the Son of God.
But I do think that Judas enjoyed an excess of pride, probably stemming from the fact that he was the scholar of the group, the "smartest" and most educated. As such, he thought he knew better than Jesus did what a proper Messiah should be like. (In many ways, it is a repeat of the sin of Adam and Eve.) In all his learning, Judas has learned to be ignorant, to blind himself to true knowledge. He put himself and his own ideas before the Truth who lived beside him everyday and, thus, began to confuse error for truth and truth for error, no longing believing that Jesus was Lord, before compounding his freely chosen evil by using an act of love to commit treachery. It is the same with our pointy-headed intelligensia today - the smartest folks in the room are often the most stupid.
Of course, we all have to guard against that temptation of thinking that you know it all, especially thinking that you know better than God how things ought to be. AND ESPECIALLY continuing to think you know better, continuing to take charge and impose your own will, even after you see that you were wrong, refusing to seek forgiveness and, instead, tying a rope around your neck and jumping from a tree. If you do that, if that is "your final answer," you will have to live, or not-live rather, with that choice.
Perhaps, in that millisecond before his neck snapped or before he took his last gasp of breath and the synapses stopped firing in his brain, perhaps in that flash of an instant Judas fully repented and sought forgiveness -- but that is not what is suggested in the Gospels. The implication of scripture, and hence the natural inference to be drawn, is that, unlike Peter, in his arrogant pride and refusal to be humble, rejecting God's gift of life and engaging in the sin of despair, Judas sadly chose the darkness.
Let us be like Peter and not Judas while there is still time.
In his talks at the Wednesday General Audiences, Pope Benedict has had occastion to consider Judas and his choice of self over God:
Jesus treated [Judas] as a friend (cf. Mt 26:50); however, in His invitations to follow Him along the way of the beatitudes, He does not force His will or protect it from the temptations of Satan, respecting human freedom.--Pope Benedict, General Audience of October 18, 2006
In effect, the possibilities to pervert the human heart are truly many. The only way to prevent it consists in not cultivating an individualistic, autonomous vision of things, but on the contrary, by putting oneself always on the side of Jesus, assuming His point of view. We must daily seek to build full communion with Him.
Let us remember that Peter also wanted to oppose Him and what awaited Him at Jerusalem, but he received a very strong reproval: "You are not on the side of God, but of men" (Mk 8:33)!
After his fall, Peter repented and found pardon and grace. Judas also repented, but his repentance degenerated into desperation and thus became self-destructive.
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.