The Son of man goeth as it is written of him: but woe unto that man by whom the Son of man is betrayed! it had been good for that man if he had not been born.
It can seem like ‘harsh words’ at first glance– here the savior of the world is saying that Judas would have been better off without the option of salvation. That sort of policy flies in the face of, say, the Catholic opposition to capital punishment: if you kill the guy, you eliminate room for the Holy Spirit to convert his soul.
However, after some reflection with a friend of mine, I’ve decided it isn’t anger or warning, but empathy and a sad realization for Jesus: perhaps the most learned and close friend of Jesus is going to betray him, and Jesus already knows this. He has known since he laid eyes on Judas that here his friend was going to be the proximate cause of his crucifixion.
I don’t even think it was his betrayal that saddened Jesus the most; it was his eventual suicide. We are all Judas when we sin; we by our apathy request that Jesus get on the cross rather than us, even though we have been commanded to it, to stick to it with our own bloodied shirt. But Judas’ suicide was the salt that fatally infected the wound of betrayal: Judas began his betrayal by handing Jesus over, and ended his betrayal by forbidding Jesus to intervene for his soul. There were lots of people that contributed to the crucifixion that Jesus doesn’t seem to upset about. But his ‘woes’ are with Judas. It is because at the last Judgment, Jesus will have no option but to stand before one of his best friends and disciples once again, and to point him downward. While there will be no broken hearts among the Just on the last day (see Dante’s Paradisio for a poetic description of the souls in heaven, while rejoicing in God’s judgment, looking down unsympathetically at the souls in hell), while on earth Jesus still mourns the coming responsibility that he will have to bear. And so he says ‘woe’ not because Judas will crucify Jesus on earth, but because Jesus is forced into the position of condemning Judas for eternity.