The Cup Jesus Chose

Part 2 in the Series: The Road to Redemption

Introduction:

As Jesus entered Jerusalem to the cries of “Hosanna!”, the people hailed Him as a liberating King—one who would overthrow Rome and restore Israel’s glory. But Jesus came to wage a deeper battle—not against political powers, but against sin and death. His triumphal entry marked not the beginning of a revolution, but the road to redemption.

That road would soon lead to an upper room, where Jesus gathered with His disciples for the Passover meal. A meal that, for generations, had celebrated God’s mighty deliverance of His people from Egypt. Yet on this night, Jesus revealed that the Passover had always pointed to something greater—a deeper deliverance yet to come.

In the traditional Passover Seder, four cups of wine are shared, each representing a promise from God in Exodus 6:6–7: sanctification, deliverance, redemption, and consummation. These cups were more than symbolic—they were prophetic. Jesus infused them with new meaning, showing how He alone would fulfill each promise.

But one cup was missing from the table that night—the Cup of Wrath. A cup not meant for celebration but for judgment. A cup Jesus would drink alone.

Today, we’ll journey through these cups—what they meant to Israel, how Jesus fulfilled them, and how one cup in particular—the Cup of Redemption—becomes our entrance into the New Covenant.

The Four Cups of the Passover: God’s Promises Remembered

The Passover meal was more than a meal—it was a story told in taste, tradition, and time. And at the heart of that story were four cups of wine, each representing a covenant promise from God in Exodus 6:6–7

Exodus 6:6–7 ESV

6 Say therefore to the people of Israel, ‘I am the Lord, and I will bring you out from under the burdens of the Egyptians, and I will deliver you from slavery to them, and I will redeem you with an outstretched arm and with great acts of judgment. 7 I will take you to be my people, and I will be your God, and you shall know that I am the Lord your God, who has brought you out from under the burdens of the Egyptians.

“I am the LORD, and I will bring you out... I will deliver you... I will redeem you... I will take you to be My people.”

I will bring you out

I will deliver you

I will redeem you

I will take you to be My people

Each of these four promises was marked by a cup:

1. The Cup of Sanctification

“I will bring you out from under the burdens of the Egyptians.” Ex.6.6

This first cup reminded Israel of God’s call to set them apart as His people. Jesus fulfilled this when He called His disciples—not just out of the world, but into a new identity and mission. He sanctifies us through His truth (John 17:17 “17 Sanctify them by Your truth. Your word is truth.” ) and brings us into fellowship with the Father.

2. The Cup of Deliverance

“I will deliver you from slavery.”

God didn’t just bring Israel out of Egypt—He broke their chains. This cup celebrates freedom from bondage. Jesus fulfills this spiritually:

“Everyone who practices sin is a slave to sin... but if the Son sets you free, you will be free indeed” (John 8:34,36). John 8:34

John 8:34 NKJV

34 Jesus answered them, “Most assuredly, I say to you, whoever commits sin is a slave of sin.

John 8:36 NKJV

36 Therefore if the Son makes you free, you shall be free indeed.

Through the cross, He delivers us not from Pharaoh, but from the far greater tyrants of sin and death.

3. The Cup of Redemption

“I will redeem you with an outstretched arm and with mighty acts of judgment.”

This is the cup Jesus lifted during the Last Supper: This is the key verse:

Luke 22:20 NKJV

20 Likewise He also took the cup after supper, saying, “This cup is the new covenant in My blood, which is shed for you.

By His blood, He secured our eternal redemption (Hebrews 9:12).

Hebrews 9:12 NKJV

12 Not with the blood of goats and calves, but with His own blood He entered the Most Holy Place once for all, having obtained eternal redemption.

Just as God redeemed Israel by the blood of the Passover lamb, Jesus redeems us by becoming the Lamb—slain from before the foundation of the world.

This cup marks the turning point—it’s not just remembrance, it’s fulfillment. The old covenant is passing. The new covenant is beginning. The new covenant is established by Christ’s blood.

4. The Cup of Praise (or Consummation)

“I will take you to be My people, and I will be your God.”

This final cup celebrates the full restoration of God’s people to Himself. But at the Last Supper, Jesus did not drink it.

Matthew 26:29 NKJV

29 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.”

He was looking ahead—to a future banquet. A future celebration. The Marriage Supper of the Lamb (Revelation 19:9), when all of God’s promises are fully realized, and we sit with Him at the table forever.

5. The Missing Cup: The Cup of Wrath

But there was one more cup—not found on the Passover table, but ever-present in the shadow of the cross.

The Cup of Wrath.

Throughout Scripture, this cup represents the righteous judgment of God against sin:

Psalm 75:8 ESV

8 For in the hand of the Lord there is a cup with foaming wine, well mixed, and he pours out from it, and all the wicked of the earth shall drain it down to the dregs.

Isaiah 51:17 ESV

17 Wake yourself, wake yourself, stand up, O Jerusalem, you who have drunk from the hand of the Lord the cup of his wrath, who have drunk to the dregs the bowl, the cup of staggering.

Jeremiah 25:15 ESV

15 Thus the Lord, the God of Israel, said to me: “Take from my hand this cup of the wine of wrath, and make all the nations to whom I send you drink it.

This cup was not part of the Passover because it was never intended for the redeemed—it was reserved for judgment. And yet, Jesus willingly chose to drink it.

In Gethsemane, He cried out:

Matthew 26:39 NKJV

39 “O My Father, if it is possible, let this cup pass from Me; nevertheless, not as I will, but as You will.”

This was no symbolic metaphor—this was the anguish of a Savior staring into the depth of divine wrath. Jesus knew that on the cross, He would drink to the bottom the penalty for every sin ever committed.

When Did Jesus Drink the Cup of Wrath?

The cross was the moment He drank the full fury of that cup.

He endured the agony of Roman scourging, the shame of the cross, the mockery of crowds. But more than that—He bore the weight of divine judgment. The curse of the law. The sin of the world.

Matthew 27:46 NKJV

46 And about the ninth hour Jesus cried out with a loud voice, saying, “Eli, Eli, lama sabachthani?” that is, “My God, My God, why have You forsaken Me?”

A direct quote from Ps. 22

He wasn’t abandoned in identity—but in experience. In that moment, He bore what we deserved, so that we would never have to bear it ourselves.

Then came a final moment, almost easy to miss:

“After this, Jesus, knowing that all was now finished, said (to fulfill the Scripture), ‘I thirst.’... They held a sponge of sour wine to His mouth... He said, ‘It is finished,’ and He gave up His spirit.” (John 19:28–30

John 19:28–30 NKJV

28 After this, Jesus, knowing that all things were now accomplished, that the Scripture might be fulfilled, said, “I thirst!” 29 Now a vessel full of sour wine was sitting there; and they filled a sponge with sour wine, put it on hyssop, and put it to His mouth. 30 So when Jesus had received the sour wine, He said, “It is finished!” And bowing His head, He gave up His spirit.

Earlier, He had refused the wine mixed with myrrh—it would dull His pain. This account is found in Mark 15.23

Mark 15:23 NKJV

23 Then they gave Him wine mingled with myrrh to drink, but He did not take it.

He would not take shortcuts through suffering. But now, He drinks the sour wine—fulfilling Psalm 69:21

Psalm 69:21 NKJV

21 And for my thirst they gave me vinegar to drink.

This was the final bitter drop. The last taste of wrath. And with it, Jesus declared:

“It is finished.”

The cup had been drained. The price paid in full.

The Great Exchange: Wrath for Blessing

And now, because He drank the cup of wrath, we drink the cup of blessing.

1 Corinthians 10:16 NKJV

16 The cup of blessing which we bless, is it not the communion of the blood of Christ? The bread which we break, is it not the communion of the body of Christ?

We don’t face wrath—we receive grace.

We don’t earn righteousness—we are given it freely:

Forgiveness through His blood (Ephesians 1:7)

Salvation as a gift (Romans 6:23)

Eternal life with Him (John 3:16)

And one day soon, we will drink the final cup with Him—the Cup of Praise at the Marriage Supper of the Lamb.

Revelation 19:9 NKJV

9 ‘Blessed are those who are called to the marriage supper of the Lamb!’ ”

Preparing Our Hearts for Communion

As we come now to the Lord’s Table, we are reminded that this is more than a ritual—it is a response to redemption.

We drink the Cup of Redemption because Jesus drank the Cup of Wrath.

We do not approach this table lightly. Paul reminds us:

1 Corinthians 11:28 NKJV

28 But let a man examine himself, and so let him eat of the bread and drink of the cup.

This is a moment of remembrance, repentance, and renewal. As the praise team come to lead us in an invitational song “Lord I Need You”

Prayer:

Heavenly Father, With hearts full of gratitude, we come before You. Thank You for sending Your Son to drink the Cup of Wrath so that we could drink the Cup of Blessing. As we partake of communion, let us remember the price of our redemption. Cleanse our hearts, renew our spirits, and draw us close to You. In Jesus’ name, Amen.