Matthew 26:1–16; Mark 14:1–11; Luke 22:3–6
1 When Jesus had finished all these sayings, he said to his disciples, 2 “You know that after two days the Passover is coming, and the Son of Man will be delivered up to be crucified.”
3 Then the chief priests and the elders of the people gathered in the palace of the high priest, whose name was Caiaphas, 4 and plotted together in order to arrest Jesus by stealth and kill him. 5 But they said, “Not during the feast, lest there be an uproar among the people.”
Jesus Anointed at Bethany
6 Now when Jesus was at Bethany in the house of Simon the leper, 7 a woman came up to him with an alabaster flask of very expensive ointment, and she poured it on his head as he reclined at table. 8 And when the disciples saw it, they were indignant, saying, “Why this waste? 9 For this could have been sold for a large sum and given to the poor.” 10 But Jesus, aware of this, said to them, “Why do you trouble the woman? For she has done a beautiful thing to me. 11 For you always have the poor with you, but you will not always have me. 12 In pouring this ointment on my body, she has done it to prepare me for burial. 13 Truly, I say to you, wherever this gospel is proclaimed in the whole world, what she has done will also be told in memory of her.”
Judas to Betray Jesus
14 Then one of the twelve, whose name was Judas Iscariot, went to the chief priests 15 and said, “What will you give me if I deliver him over to you?” And they paid him thirty pieces of silver. 16 And from that moment he sought an opportunity to betray him.
We have followed Jesus from his donkey ride into Jerusalem (Palm Sunday), to his cleansing of the temple courts (Monday), to his confrontation with the chief priests and elders at the temple (Tuesday), and now to the deal that finances Jesus’ death, a scene traditionally commemorated by the Church on Spy Wednesday.
But before we consider the Spy Wednesday passage of Mt 26:1–16, let’s set the stage by tracing the events leading up to this pivotal scene.
After Jesus had foiled the religious leaders’ attempt to entrap him with a question of John the Baptist’s authority, he remained at the temple, preaching the kingdom of God to the crowds (Mt 21:28–22;14), debating and rebuking the Pharisees and Sadducees (Mt 22:15–23:36), and lamenting over Jerusalem’s history of defiance toward God and his prophets (Mt 23:37–39).
When Jesus finally leaves the temple, the disciples with him marvel at its monumental size. But to their surprise, Jesus foretells the temple’s destruction—one day the holy city will burn in ruin (Mt 24:1–2).
From there, Jesus leads the disciples up the Mount of Olives where they find a spot on the slope to sit. It’s been an eventful day to say the least. There, overlooking Jerusalem to their west, the disciples ask Jesus to explain when the temple will fall and when he will finally usher in a new era. And so, in a scene known as the “Olivet Discourse,” Jesus foretells what is to come, though he continues to speak in riddles and parables (Mt 24:3–25:46).
With the close of the Olivet Discourse, we turn the page to Matthew 26, where a pivotal development unfolds, marking the beginning of the end.
Sitting on the Mount of Olives, Jesus tells the disciples that the “Son of Man” will soon be crucified. Simultaneously, somewhere in Jerusalem, the chief priests and elders gather in the palace of Caiaphas, the high priest, to plot Jesus’ arrest and death (Mt 26:1–5). Two conversations—one sincere, one sinister. Two locations—one humble, one haughty. Both anticipate one death.
Matthew teases out this duality in the verses that follow. In a first scene, an unnamed woman arrives at Simon the leper’s house in Bethany with a jar of fragrant oil worth a year’s wages, and she pours it on Jesus’ head (Mt 26:6–13; Mark 14:5; John 12:5). The disciples call her act a “waste,” but Jesus, absorbing not only the oil in his hair and skin but the symbolism of the moment, defines her act as kalos, “beautiful.” Kalos is the same word Jesus uses to speak of “good” works that bring glory to God: “let your light shine before others, so that they may see your good (kalos) works and give glory to your Father who is in heaven” (Mt 5:16).
Yet, in the shadows of kalos devotion, betrayal is afoot. Judas steals away, and for thirty pieces of silver, a month’s wages, he cuts a deal with the chief priests to deliver Jesus into their hands (Mt 26:14–16).
Two followers—one unnamed woman, one named man. Two prices—one extravagant, one moderate. Two acts—one devotion, one betrayal. Both centered on the same messiah.
For the believer, the duality of Matthew’s narrative captures our human struggle with sin. Often, we live in contradiction, and we beat ourselves up for it. The Apostle Paul admitted the struggle in his own life: “For I do not understand my own actions. For I do not do what I want, but I do the very thing I hate… Wretched man that I am! Who will deliver me from this body of death?” (Rom 7:15, 24).
Some days we’re the unnamed woman. Other days we are Judas. Every day we need God’s grace. But here’s the thing about grace that’s often forgotten—you don’t earn it, you don’t have to suffer for it, to beat yourself up for it, to prove you deserve it. If you had to do any of that, it wouldn’t be grace.
You might know this truth in theory but struggle to live as if it’s real for you. The enemy wants nothing more than to see a child of God living as if they were disowned.
If this sounds like your story, then perhaps breakthrough looks like freedom to walk in the fullness of God’s grace. Perhaps it looks like the Apostle Paul, who, after admitting his own struggle with sin, declares in the same breath, “Thanks be to God through Jesus Christ our Lord! … There is therefore now no condemnation for those who are in Christ Jesus” (Rom 7:25–8:1).
Take time to contemplate the following questions in conversation with the Spirit:
What have been some “unnamed woman” moments in my life, where I sensed the loving nearness of Christ?
Where do I trade loyalty to Christ for earthly pleasure or gain?
What’s holding me back from walking in the freedom of the Father’s grace?
Let’s pray: Gracious Father, like the Apostle Paul, sometimes I just don’t understand myself. Sometimes I’m the unnamed woman, serving you faithfully. Other times I’m Judas, messing up. In fact, I can be pretty wretched. I want to make you proud by how I live, think, and speak, but then I do the very opposite of what is good, what is kalos. So, I need your grace. Teach me to live in faithful obedience, and send me encouragement along the way, so that I can be like Paul, able to lament my sin while confident in your kindness toward me. I want to live in the full freedom of your grace, secure in my identity as your child. So, I’m trusting you, Lord, because you never fail. Receive my prayer in Jesus’ name, amen.
Written by Pastor Anthony Lipscomb