Matthew 26:17-30 - The Last Passover

Hey everyone. My name is Josh, and I’m one of the pastors here at The Well. I am thankful for the opportunity to open God’s Word with you today from Matthew chapter 26, verses 17 through 30.

In most families, mine included, we have certain stories from our family history that teach core lessons and truths we really want to pass down from generation to generation. In my family, there are things I want my three sons to know about their heritage. For example, I want them to know that their grandfather, James Holly, was a Marine in World War II fighting in the Pacific. He survived the attack on Pearl Harbor, the Battle of Midway, and Guadalcanal. He won two awards for uncommon valor in the face of enemy fire, and he never even told anybody. We didn’t find out until after he died, when my uncle found the medals in a box up in an attic.

I also want them to know that my grandparents on my mother’s side, Eladio and Delmira, were migrant farm workers right here in the Central Valley. They worked hard to provide a better future for their kids, and were able to earn enough money to buy not one, but two homes right here in Pinedale. One of the things my grandmother used to say was, “Never be ashamed of dirty hands, because they show that you know how to work hard.” These are core truths I want my sons to understand about who they are and about their heritage.

In the same way, when we look at God’s Word, we see that there are certain core truths and stories in the history of God’s people that He wants His family to know generation after generation. We’re going to look at a couple of those today.

The Kairos Moment

Last week, Pastor Mike Sladen kicked off our mini-series in Matthew called The Last Days, as we journey through the climax of this gospel. We looked at three different groups of people: the religious leaders who wanted nothing to do with Jesus; Judas, who viewed Jesus like a genie to conform to his own agenda; and Mary, who sat at the feet of Jesus with a heart of sacrificial, deeply personal worship.

At the beginning of chapter 26, we are nearing the Passover feast. Let’s pick up that narrative in verse 17.

Matthew 26:17-19 (NASB)

Now on the first [day] of Unleavened Bread the disciples came to Jesus and asked, ‘Where do You want us to prepare for You to eat the Passover?’ And He said, ’Go into the city to a certain man, and say to him, ’The Teacher says, ‘My time is near; I [am to] keep the Passover at your house with My disciples.’‘’ The disciples did as Jesus had directed them; and they prepared the Passover.

Here we have described the Passover and the Feast of Unleavened Bread. These two events roll right into each other: the Passover feast is a one-day event, followed immediately by the Feast of Unleavened Bread over seven days, creating an eight-day festival that Israel had celebrated for over fifteen hundred years.

The origins go back to the book of Exodus. The Hebrews were enslaved in Egypt, and God raised up Moses to deliver them. God sent plagues to turn Pharaoh’s heart, but Pharaoh refused to let God’s firstborn go. So God announced the tenth and final plague: the death of the firstborn in Egypt. But He instructed the Hebrews that their homes would be spared when the angel of death came if they slaughtered a spotless lamb, sprinkled its blood on the doorposts, roasted the lamb, and ate a feast. When the angel of death saw the blood on the doorpost, he passed over that house.

The Egyptians suffered the loss of their firstborn, and in distress Pharaoh ordered Moses to get out immediately. They left in such haste that their bread did not have time to rise, which is why they ate unleavened bread. God commanded Israel to practice this feast every year so they would always remember His deliverance.

Celebrating Passover was a huge logistical undertaking. Disciples had to secure a room, gather bitter herbs, wine, unleavened bread, and a sacrificial lamb. Potentially over a million pilgrims crammed into Jerusalem, a city with walls spanning only about two and a half miles. That is a social distancing nightmare! Over 100,000 lambs would be slaughtered in a single day at the temple. In fact, so much blood flowed from the altar into the Kidron Valley that the brook ran crimson red—a vivid reminder that the atonement of sin requires the shedding of blood.

When the disciples ask where to prepare, Jesus replies, “My time is at hand.”

In Greek, there are two words for time: chronos, which refers to chronological succession (one o’clock, two o’clock, Monday, Tuesday), and kairos, which describes an appointed, predetermined, momentous window of opportunity. Jesus is saying, “This is a kairos moment.”

Luke’s gospel tells us that Jesus gave these instructions privately to Peter and John. Why the secrecy? Because Judas was actively looking for an opportunity to betray Him. If Judas had known the location in advance, the temple guards would have arrested Jesus before the meal. But Jesus was in complete control of every single moment leading up to His death. He would not let Judas dictate the timeline. Jesus wanted this final evening in intimate fellowship with His disciples.

Treachery and Sovereignty at the Table

When evening comes, they gather in the upper room.

Matthew 26:20-25 (NASB)

Now when evening came, Jesus was reclining [at the table] with the twelve disciples. As they were eating, He said, ‘Truly I say to you that one of you will betray Me.’ Being deeply grieved, they each one began to say to Him, ‘Surely not I, Lord?’ And He answered, ’He who dipped his hand with Me in the bowl is the one who will betray Me. ‘The Son of Man [is to] go, just as it is written of Him; but woe to that man by whom the Son of Man is betrayed! It would have been good for that man if he had not been born.’ And Judas, who was betraying Him, said, ‘Surely it is not I, Rabbi?’ Jesus said to him, ‘You have said [it] yourself.’

Traditionally, the Passover meal involved four cups of wine to commemorate the four promises of God in Exodus 6. Somewhere between the third and fourth cup, Jesus drops a bombshell: one of the twelve will betray Him.

Jesus had spoken of His death before, but He had never revealed that the betrayer was inside their circle. The disciples are deeply grieved and begin asking, “Surely not I, Lord?” When Judas asks, notice the subtle shift: he asks, “Surely not I, Rabbi?” The other disciples call Him Lord, recognizing His Messiahship and authority; Judas calls Him Rabbi, a term of respect for a human teacher, but nothing more. It is a revealing slip of the heart.

Jesus notes that the betrayer is the one dipping his bread in the bowl with Him. In ancient Near Eastern culture, sharing a dish from a seat of honor was a supreme sign of intimacy and friendship. To betray someone right after sharing a meal in that position was doubly treacherous.

Jesus also refers to Himself twice in verse 24 as the “Son of Man.” That was Jesus’ favorite title for Himself. In Ezekiel, “son of man” highlights human lowliness and frailty compared to God. But in Daniel 7, the “Son of Man” is a heavenly, divine figure who receives an everlasting kingdom. By using this title, Jesus simultaneously declares His full humanity and His full deity. The One being betrayed is God incarnate.

Jesus states that He goes as it is written of Him, fulfilling the prophecy of Psalm 41:9.

Psalms 41:9 (NASB)

Even my close friend in whom I trusted, Who ate my bread, Has lifted up his heel against me.

Acts 1:16 (NASB)

’Brethren, the Scripture had to be fulfilled, which the Holy Spirit foretold by the mouth of David concerning Judas, who became a guide to those who arrested Jesus.

Jesus then speaks a sobering word: “It would have been good for that man if he had not been born.” Shortly after the betrayal, Judas is overwhelmed with remorse, flings the blood money back into the temple, and takes his own life. Yet that earthly misery is nothing compared to facing an eternity separated from God.

Here we see divine sovereignty and human responsibility operating side by side. Scripture foretold this betrayal, yet Judas bore full moral responsibility for his crime against God. When Jesus looks across the table and warns what awaits the betrayer, you can almost hear the pastoral appeal: Judas, look at Me. Think about what you are about to do. Look into the eyes of the Savior who loves you.

That is often how God intervenes when we face premeditated sin. Through His Word, His Spirit, and His people, He prompts us: Stop. Think about the consequences. Look at the Savior and turn around. But Judas hardened his heart, got up, and walked out into the night.

The Last Passover, The First Communion

With Judas gone, Jesus institutes something brand new.

Matthew 26:26-30 (NASB)

While they were eating, Jesus took [some] bread, and after a blessing, He broke [it] and gave [it] to the disciples, and said, ‘Take, eat; this is My body.’ And when He had taken a cup and given thanks, He gave [it] to them, saying, ’Drink from it, all of you; for this is My blood of the covenant, which is poured out for many for forgiveness of sins. ‘But I say to you, I will not drink of this fruit of the vine from now on until that day when I drink it new with you in My Father’s kingdom.’ After singing a hymn, they went out to the Mount of Olives.

In this sacred moment, Jesus transforms the Passover into the Lord’s Supper. The last Passover becomes the first Communion.

Jesus shows them that the entire fifteen-hundred-year history of Passover was pointing directly to Him. The Passover lamb pointed to the ultimate Lamb of God who takes away the sin of the world. The blood on the doorposts that spared the firstborn from wrath pointed to the blood of Christ that shields us from the judgment of God. Deliverance from slavery in Egypt pointed to our deliverance from slavery to sin, Satan, and death.

John 1:29 (NASB)

The next day he saw Jesus coming to him and said, ’Behold, the Lamb of God who takes away the sin of the world!

Jesus declares, “This is My blood of the covenant, which is poured out for many for forgiveness of sins.” Luke adds that Jesus called it the new covenant.

In the Old Testament, covenants between God and humanity contained blessings conditioned on obedience. But humanity failed continually. In this new covenant, God fulfilled both the divine and human requirements Himself. God the Son took on flesh, lived the perfect life we could not live, and died the death we deserved. He fulfilled Jeremiah’s prophecy of a new covenant written on human hearts.

Jeremiah 31:31-34 (NASB)

‘Behold, days are coming,’ declares the LORD, ‘when I will make a new covenant with the house of Israel and with the house of Judah, not like the covenant which I made with their fathers in the day I took them by the hand to bring them out of the land of Egypt, My covenant which they broke, although I was a husband to them,’ declares the LORD. ‘But this is the covenant which I will make with the house of Israel after those days,’ declares the LORD, ’I will put My law within them and on their heart I will write it; and I will be their God, and they shall be My people. ’They will not teach again, each man his neighbor and each man his brother, saying, ‘Know the LORD,’ for they will all know Me, from the least of them to the greatest of them,’ declares the LORD, ‘for I will forgive their iniquity, and their sin I will remember no more.’

Through the Holy Spirit, God writes His law upon our hearts, transforming us from the inside out so we can walk with Him in grace. The hero of the Bible is not Abraham, Moses, or David—they were flawed men in desperate need of grace. The only true hero of the story is Jesus Christ.

When we take Communion, the bread reminds us of His physical body, beaten and nailed to a cross to bear God’s wrath in our place. The cup reminds us of His blood shed to seal our forgiveness. Communion is not only a memorial looking back; it is also a anticipation looking forward. Jesus promises He will drink the fruit of the vine anew with us in His Father’s kingdom. There is coming a day when we will sit at the table with Jesus, free from sin, pain, and sorrow forever.

Living as Ambassadors

When you examine your life today, what uncertainties, fears, or disappointments are you facing? Perhaps someone you love is making destructive choices, or perhaps you are struggling with choices of your own. Jesus never promised an easy life free of trials, but He promised His enduring presence. He uses every circumstance to shape us into His image.

Hebrews 12:2 (NASB)

fixing our eyes on Jesus, the author and perfecter of faith, who for the joy set before Him endured the cross, despising the shame, and has sat down at the right hand of the throne of God.

Ephesians 1:4-5 (NASB)

just as He chose us in Him before the foundation of the world, that we would be holy and blameless before Him. In love He predestined us to adoption as sons through Jesus Christ to Himself, according to the kind intention of His will,

Look at the world around us. Systems fracture, cultural tensions run high, and fear grips many hearts. This brokenness is a glaring reminder of how desperately our world needs Jesus. Communion anchors our identity and reminds us of our mission: we are ambassadors for Christ.

2 Corinthians 5:20 (NASB)

Therefore, we are ambassadors for Christ, as though God were making an appeal through us; we beg you on behalf of Christ, be reconciled to God.

The early church lived under an oppressive Roman regime in a culture riddled with abandonment, injustice, and hostility. Yet they did not retreat into bitterness or political hostility. They rescued abandoned infants, cared for the poor across social barriers, elevated women, and lived with radical generosity. Even their enemies noted that Christians cared for pagan poor alongside their own.

Ephesians 1:15-16 (NASB)

For this reason I too, having heard of the faith in the Lord Jesus which [exists] among you and your love for all the saints, do not cease giving thanks for you, while making mention [of you] in my prayers;

The world does not need more anger or political shouting from Christians. What our world needs is Jesus Christ, crucified and risen. He alone has the power to change human hearts and bring true reconciliation.

Let us be a people who make Christ known through faith, hope, and sacrificial love.

Let’s pray together.

Father, we come before You in the name of Jesus. In this broken world, we ask that You work through the power of Your Spirit in our lives so that people around us would be drawn to faith in Christ. In the midst of uncertain times, bring people to repentance and faith. Teach those of us who carry the name of Christ to live in deeper, daily dependence on Him. In all things, may You be glorified. We pray this in Jesus’ name. Amen.