Welcome:

Last week we concluded our series on the Sermon on the Mount. Today we’re turning to the passion narrative of Christ as we move towards the celebration of Easter. This morning we will be in  Matthew 26:17–30, where Jesus shares His final meal with His disciples before the cross.

Scripture Reading: 

Matthew 26:17-30 ESV

Now on the first day of Unleavened Bread the disciples came to Jesus, saying, “Where will you have us prepare for you to eat the Passover?” He said, “Go into the city to a certain man and say to him, ‘The Teacher says, My time is at hand. I will keep the Passover at your house with my disciples.’” And the disciples did as Jesus had directed them, and they prepared the Passover.

When it was evening, he reclined at table with the twelve. And as they were eating, he said, “Truly, I say to you, one of you will betray me.” And they were very sorrowful and began to say to him one after another, “Is it I, Lord?” He answered, “He who has dipped his hand in the dish with me will betray me. The Son of Man goes as it is written of him, but woe to that man by whom the Son of Man is betrayed! It would have been better for that man if he had not been born.” Judas, who would betray him, answered, “Is it I, Rabbi?” He said to him, “You have said so.”

Now as they were eating, Jesus took bread, and after blessing it broke it and gave it to the disciples, and said, “Take, eat; this is my body.” And he took a cup, and when he had given thanks he gave it to them, saying, “Drink of it, all of you, for this is my blood of the covenant, which is poured out for many for the forgiveness of sins. I tell you 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.”

And when they had sung a hymn, they went out to the Mount of Olives.

I. The Sovereign Preparation for Redemption (Matthew 26:17–19)  

Our passage this morning opens with Matthew saying, “Now on the first day of Unleavened Bread…” (Matthew 26:17). The timing is full of meaning. Exodus 12:18 commands, “From the fourteenth day…you shall eat unleavened bread.” And now, on that very evening, Jesus isn’t just observing the tradition, He embodies it. The bread, the wine, and the lamb all point to Him. This is the day God’s people remembered how the blood of the lamb spared them in Egypt. Now, the true Lamb of God is preparing to offer Himself for our deliverance.

In verse 18, Jesus says, “Go into the city to a certain man…My time is near.” That phrase “a certain man” may sound vague, but it’s not random. Jesus had already arranged everything. He wasn’t reacting to events; He was directing them.

When He says, “My time is near,” He’s pointing to a specific, appointed moment. The Greek word “kairos” refers not to clock time, but to a decisive, purposeful moment. In John 10:18, Jesus says, “No one takes my life from me…I lay it down of my own accord.” That’s exactly what we see here. Jesus is walking toward suffering willingly, because saving us was always the plan.

The cross wasn’t a surprise to God, and neither is your salvation. Jesus chose it, and the same sovereign hand holds your life, too. If God can bring redemption through betrayal and pain, He can bring purpose to your pain as well. That’s what trust looks like, not just in peace, but in the shadow of the cross. Life may catch us off guard, but never God. As we approach Easter, remember: Jesus didn’t stumble into death. He marched into it, on purpose, for us.

II. The Betrayal Foretold: The Tragedy of a Hardened Heart (Matthew 26:20–25)  

Now this Passover celebration that Jesus was preparing for was a sacred time for Israelites to remember the Exodus from Egypt, when the Lord passed over them in mercy. And yet, in that sacred moment, a shadow loomed. Matthew tells us: “When it was evening, he reclined at table with the twelve. And as they were eating, he said, ‘Truly, I say to you, one of you will betray me.’” (Matthew 26:20–21, ESV)

Again we see that Jesus is not caught off guard. He knows the hearts of men. He knows his betrayer, and yet, He still shares the table with him. Judas, the betrayer, is not pushed out. He is served. He is included. His feet were washed. His place at the table was prepared. Jesus extends fellowship, even to the one who is already turning against Him.

John Chrysostom, one of the early Christian teachers, marveled at this, noting that Jesus spares the traitor by not naming him outright. He says only, “One of you will betray me.” It is as if, even in this moment, Christ is offering Judas space to repent. He lets all the others feel the weight of uncertainty, just to give this one man a final chance to turn back. This is not weakness on Christ’s behalf. It is love. It is the patience of God on full display. 

And then comes the moment of self-examination. “And they were very sorrowful and began to say to him one after another, ‘Is it I, Lord?’” (Matthew 26:22) Each disciple hears Jesus’ words and immediately turns inward. They don’t point fingers. They don’t accuse. They ask, “Is it I, Lord?” They ask this because they understand their own weakness. They know human nature is fragile. They know the enemy is real. They know none of them are above temptation. 

But Judas answers differently. Matthew tells us, “Judas, who would betray him, answered, ‘Is it I, Rabbi?’” (v. 25) Do you hear the difference? The others say “Lord.” Judas says “Rabbi.” That shift is no accident. In Matthew’s Gospel, Judas never calls Jesus “Lord.” It’s always “Rabbi” teacher. Instructor. That small word reveals a massive truth: the betrayal didn’t begin with silver coins. It began with a heart that was attracted to Jesus’ teachings, but who never fully submitted to the Lordship of Christ. 

Jesus then declares, “The Son of Man goes as it is written of him, but woe to that man by whom the Son of Man is betrayed! It would have been better for that man if he had not been born” (Matthew 26:24).  Jesus is going to the cross “as it is written.” The plan of redemption is unfolding exactly as God has declared. The betrayal is no surprise. The Scriptures are being fulfilled. And yet, “woe to that man.”

This is the mystery of divine sovereignty and human responsibility. God’s plan is never thwarted. He is in full control. And yet we are still responsible for what we do. Judas isn’t a puppet, he’s a man with a hardened heart. He chose greed over grace. He chose proximity to Jesus over surrender to Him. And Jesus says it would have been better for him not to be born. God may use all things for His purpose, but that doesn’t lessen the weight of our choices.

Paul echoes this warning in 1 Corinthians 11:28: “Let a person examine himself, then, and so eat of the bread and drink of the cup.” Before we sit at the Lord’s table, we must ask hard questions: Who is Jesus to me? Can I say with full confidence and assurance that He is my Savior and my Lord? Make no mistake, it is possible to be close to Jesus, to serve in His name, to sit at His table, and still have a heart far from Him.

III. The Bread and Cup: A New Covenant is Sealed (Matthew 26:26–28)  

Now let’s turn our eyes from Judas, to the one who is truly the focus of this passage. Jesus takes the bread, the same bread that every Jew at that Passover table had eaten since childhood, and He gives it new meaning: “This is my body” (Matthew 26:26, ESV). What had once been the bread of affliction in Egypt now becomes the bread of redemption. 

The broken bread is a picture of His body soon to be broken on the cross. And He gives thanks before He breaks it, because He is not a victim. He is a willing Savior. Christ gives thanks even as He prepares to suffer, teaching us to meet hardship with gratitude, because God’s purpose is still unfolding. And this bread becomes the sign of His presence with us until He comes again. 

Then Jesus takes the cup. He gives thanks. He lifts it. And He says something no rabbi had ever said at Passover: “This is my blood of the covenant, which is poured out for many for the forgiveness of sins” (Matthew 26:28, ESV). That cup, filled with wine, now holds a new meaning. It echoes the covenant blood that Moses sprinkled on the people in Exodus 24:8, “Behold the blood of the covenant that the Lord has made with you.” It echoes Jeremiah 31:31–34, “I will make a new covenant... I will forgive their iniquity, and I will remember their sin no more.” And it echoes Isaiah 53:12, “He poured out his soul to death... yet he bore the sin of many.” The blood of Jesus is covenant blood. It is sacrificial blood. And it is forgiving blood. This cup is not just a symbol of suffering, it is the fountain of mercy. 

In that upper room, Jesus wasn't ending a tradition, He was fulfilling it. The Passover lamb pointed to this moment. The bread of old was just a shadow of this bread. The wine of old was just a forerunner to this cup. The law was a tutor. Christ is the fulfillment. Jesus is both the giver of the law and its goal. What was foreshadowed is now fulfilled. What was promised is now present. The disciples couldn’t yet grasp the full meaning. But they would. After the resurrection, after Pentecost, the bread and cup would no longer be ritual, they would be revelation.

Today when we receive the bread and the cup, we are preaching with our hands what we believe in our hearts: that Christ died for sinners, and we are among them. When we eat, we are nourished by grace. When we drink, we are cleansed anew. This meal doesn’t save us, but it strengthens us, sustains us, and speaks to us. So every time we gather and partake of the bread and cup, whether in joy or sorrow, in strength or weakness, we come to a covenant sealed with Christ’s blood. As Christ himself declared, “This is my blood of the covenant, which is poured out for many for the forgiveness of sins” (Matthew 26:28, ESV).

IV. The Promise of the Kingdom (Matthew 26:29–30)  

Now Jesus had just taken the bread and the cup. He had redefined the Passover. He had spoken of brokenness, of blood, of betrayal. The atmosphere at that table must have been thick with confusion, sorrow, even fear. And yet Jesus ends the meal not with despair, but with a promise. “I tell you 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.” (Matthew 26:29, ESV). Here, Christ is looking past the cross to the crown. He’s pointing His disciples, and us, to the coming Kingdom. 

Jesus, the Bridegroom, is saying: “I’m not drinking again, not until we’re all together at the wedding feast.” It’s like a groom waiting for the wedding day to share the toast with his bride. He says, “until that day.” That day is the day of the Kingdom, the day when the wine will be poured in celebration, not in sorrow. The day of joy, reunion, restoration. This is more than a metaphor. It points to the end times banquet, the great feast promised in Isaiah 25, where “the LORD of hosts will make for all peoples a feast of rich food, a feast of well-aged wine... and he will swallow up death forever” (Isaiah 25:6–8, ESV).

Jesus is the Lamb, and yet He will be the Host. He is going to suffer, but He is also going to rise. He is going to die, but He is also going to dine again. This was His way of speaking of the resurrection. The wine of the Kingdom would be “new” because it would be shared in new, resurrection life. No longer in a body subject to death, but in an incorruptible, victorious body.

And then, after Jesus makes this incredible promise, Matthew says simply: “And when they had sung a hymn, they went out to the Mount of Olives.” (Matthew 26:30, ESV). Now that might seem like a minor detail. But don’t rush past it. Can you imagine Jesus singing, knowing that this day would include His arrest, trial, and crucifixion? He knows all of this, and yet He sings. That hymn, sung on the way to Gethsemane, reminds us: worship always goes before the weight of trials. Praise equips us for perseverance. Jesus waked towards the cross with a song.

Conclusion:

This morning we took Communion, but it’s more than remembrance. We look back to the cross, but we also receive grace now, strengthened by His Spirit. And we look ahead, to the day we’ll share the table with Him in His Kingdom. Revelation 19:9 says, “Blessed are those invited to the marriage supper of the Lamb.” That’s us, the Church. For now, we take Communion in a broken world, but we do it with hope. Every cup is a foretaste. Every piece of bread points forward. One day, sorrow will turn to celebration, and we’ll see the Lamb face to face.