The Wednesday before Easter has an unusual moniker in some Christian expressions of faith. The most traditional is "Holy Wednesday," which acknowledges the holiness of the fulfillment of Scriptures in the life of Christ (see Zechariah 11:12-13). But my favorite label for the day is "Spy Wednesday," indicative of the work of Judas on that day as he conspired with the Sanhedrin to betray Jesus for thirty silver coins.
It seems pretty clear from Matthew 26, Mark 14 and John 12 that what sent Judas over the edge was the anointing of Jesus' feet with costly perfume. Clearly he was standing pretty close to that edge already. Perfume? Feet? Get over it. I love how John tells it like it really is. While all three Gospel writers admit the disciples were miffed the perfume hadn't been sold to help the poor, John tells the REAL truth, Judas "said this, not because he was concerned about the poor, but because he was a thief, and...he used to pilfer what was put into [the money box]" (vs. 7). What's amazing to me is it appears everybody already knew that about his character. There certainly wasn't time for him to have confessed his thievery at any point following the upcoming events. And even knowing the truth about Judas' behaviors, Jesus had still let him be in charge of the group's financial assets! Judas is a biblical Bernie Madoff! (Which shows Jesus isn't afraid of or threatened by any economy or financial investor, so we shouldn't be either. But that's a side note.)
I can just hear Judas' rationale for his theft, "I'm one of the poor. I don't have a steady job or income since I'm following Jesus around all the time. And don't I deserve this for all the times I've preached, healed and removed demons (Luke 9:1-6), distributed and picked up baskets of food (Matthew 14), endured his sermons on humility (Mark 9:35), helped arranged meals (Matthew 26:17-19), stayed with him when he didn't make sense (John 6:66-71), stood by him against the Pharisees (Mark 8:10-11)? Wow, I'm a pretty good guy for doing all this!"
Judas' selfish greed extended much deeper within his soul than just the desire for money. Greed is merely an expression, a symptom, if you will, of a greater and more cancerous illness: pride. And I think that's what sent him over the edge with Jesus. When he saw the love and forgiveness exuding from Jesus to the woman annointing him, Judas' pride couldn't take it. "How dare he show such mercy? How dare he offer such extravagant grace? I can't even stand to be in the presence of such a sinful woman--whose sin is so much greater than my own." If only he'd admitted his own sin at that moment and fallen at Jesus' feet with her, how different the story might have been for him.
Instead, his self-righteous pride grew deeper roots and suffocated any seeds of humility or repentance planted in his soul, so that when the opportunity presented itself, he found the Sanhedrin and offered them his support toward killing Jesus in exchange for money. And he began looking for the chance to betray Jesus. Spy Wednesday, indeed.