Day 2: Anointing, Supper, and Gethsemane

Reading: Matthew 26:1-46

Listen to: Matthew chapter 26

Historical Context

Matthew 26 opens with Jesus making his fourth and final Passion prediction: “You know that after two days the Passover is coming, and the Son of Man will be delivered up to be crucified” (26:2). The calm precision of this statement is remarkable. Jesus names the time (two days), the occasion (Passover), and the method of death (crucifixion). He is not a passive victim overtaken by events; he is a sovereign actor who knows exactly what is coming and walks toward it with open eyes. Meanwhile, in a grim counterpoint, the chief priests and elders gather in the palace of Caiaphas to plot his arrest “by stealth” – they want him dead, but not during the feast, “lest there be an uproar among the people.” The irony is that Jesus will die precisely during the feast, because God’s timing overrides human scheming. The Passover lamb must die at Passover.

The anointing at Bethany provides one of the most poignant moments in the Passion narrative. An unnamed woman (identified as Mary of Bethany in John 12:3) breaks an alabaster flask of very expensive ointment and pours it over Jesus’ head. Alabaster was a translucent stone quarried primarily in Egypt, prized for its beauty and its ability to preserve the fragrance of perfume. The flask would have been sealed; breaking it meant the entire contents were used at once – an extravagant, irreversible act. The disciples (Judas in particular, according to John’s account) react with indignation: “Why this waste?” They calculate the ointment’s value at more than three hundred denarii, roughly a year’s wages for a common laborer. The objection sounds compassionate – the money could have been given to the poor – but Jesus sees more deeply. “She has done a beautiful thing to me,” he says. “In pouring this ointment on my body, she has done it to prepare me for burial” (26:12). Whether or not the woman understood the full significance of her act, Jesus interprets it as a prophetic anointing for his death. In a narrative dominated by betrayal, denial, and abandonment, this woman’s lavish devotion stands as a rebuke to every calculating heart. Jesus declares that wherever the gospel is preached in the whole world, what she has done will be told in memory of her – a promise that has been fulfilled for two thousand years.

Matthew then records Judas’ approach to the chief priests: “What will you give me if I deliver him over to you?” (26:15). The price – thirty pieces of silver – echoes Zechariah 11:12-13, where the prophet receives the same paltry sum as the “lordly price” at which the shepherd of Israel was valued by his ungrateful people. It was also the price specified in Exodus 21:32 as compensation for a slave gored by an ox. The Messiah, the Son of God, is valued at the price of a dead slave.

The Last Supper account in Matthew closely parallels Luke’s but adds the significant detail that the cup is poured out “for the forgiveness of sins” (26:28) – a phrase unique to Matthew’s version. This connects the new covenant directly to its primary benefit: the remission of sin that the sacrificial system could only foreshadow. Jesus also adds a note of eschatological hope: “I will not drink again of this fruit of the vine until that day when I drink it new with you in my Father’s kingdom” (26:29). The Lord’s Supper is not only a memorial looking back to the cross but an anticipation looking forward to the messianic banquet.

The Gethsemane scene in Matthew is the most detailed of the Synoptic accounts and stands as one of the most theologically important passages in all of Scripture. Jesus takes Peter, James, and John – the inner circle who witnessed the Transfiguration – deeper into the garden. “My soul is very sorrowful, even to death,” he tells them, echoing the language of Psalms 42:5 and 43:5. The Greek word for “sorrowful” (perilypos) suggests a grief that completely surrounds and engulfs. Luke’s Gospel adds that Jesus’ sweat became “like great drops of blood falling down to the ground” (Luke 22:44), a condition known medically as hematidrosis, which can occur under conditions of extreme psychological stress when capillaries in the sweat glands rupture.

Jesus’ prayer in Gethsemane is the most revealing window into his inner life recorded anywhere in the Gospels. “My Father, if it be possible, let this cup pass from me, yet not as I will, but as you will” (26:39). The “cup” is not merely the physical suffering of crucifixion, horrendous as that was. Throughout the Old Testament prophets, the “cup” is consistently the cup of God’s wrath against sin (Isaiah 51:17, 22; Jeremiah 25:15-16; Ezekiel 23:31-34; Habakkuk 2:16). What Jesus is facing is the prospect of bearing in his own person the accumulated judgment that the holy God of the universe has against every sin ever committed by every human being who ever lived. The weight of this prospect is what crushes him to the ground. He prays three times, each time submitting his will to the Father’s. The submission is not passive resignation but active, costly obedience. The writer of Hebrews captures it: “In the days of his flesh, Jesus offered up prayers and supplications, with loud cries and tears, to him who was able to save him from death, and he was heard because of his reverence” (Hebrews 5:7). He was heard – not by being delivered from the cup but by being given the strength to drink it.

The disciples, meanwhile, sleep. Three times Jesus finds them unconscious, and his words to Peter are both compassionate and devastating: “So, could you not watch with me one hour?” (26:40). The one who swore he would die with Jesus cannot stay awake for sixty minutes. “The spirit indeed is willing, but the flesh is weak.” This is not an excuse; it is a diagnosis. The human condition is one of aspiration without capacity, of desire without strength. Only the one who is praying – the Son whose will aligns with the Father’s through agony – has the power to do what love requires.

Key Themes

• Extravagant devotion – The woman’s anointing stands as the model of worship that gives without calculating cost
• The cup of wrath – Gethsemane reveals the true horror of the cross: not merely physical death but the bearing of divine judgment against sin
• Obedient submission – Jesus’ prayer demonstrates that true obedience does not eliminate anguish but perseveres through it

Connections

• Old Testament Roots: Zechariah 11:12-13 (thirty pieces of silver); Isaiah 51:17, 22 (the cup of God’s wrath); Psalm 42:5-6 (“Why are you cast down, O my soul?”)
• New Testament Echoes: Hebrews 5:7-9 (Jesus learning obedience through suffering); 2 Corinthians 5:21 (“he made him to be sin who knew no sin”); Philippians 2:8 (“obedient to the point of death”)
• Parallel Passages: Mark 14:1-42; Luke 22:39-46; John 12:1-8; John 18:1

Reflection Questions

1. What does the woman’s anointing teach about the relationship between extravagant worship and practical service – must we choose between them, or is there a deeper unity?
2. Why is it important to understand the “cup” in Gethsemane as the cup of divine wrath rather than simply the suffering of crucifixion?
3. Jesus asked his disciples to “watch and pray” with him, and they failed. What does this failure reveal about the limits of human willpower, and where do you see the same pattern in your own spiritual life?

Prayer

Father, we tremble before the scene in Gethsemane. Your Son, who knew no sin, fell on his face and asked whether the cup of your wrath could pass – and then drank it for us. We are like the sleeping disciples: willing in spirit, weak in flesh, unable to stay awake for even an hour. Forgive our drowsiness and strengthen us by the same Spirit who strengthened your Son. May our lives be an offering as lavish as the woman’s ointment, poured out without reserve for the one who poured out everything for us. Amen.