Understanding the Kingdom

Happy eighteenth birthday to The Well! It has been an incredible journey since 2002, seeing all that God has done in our midst. I have been blessed to be part of it since 2004, wearing a lot of different hats over the years. I am so glad to be back with you in the Word today, and we are trusting for God’s grace as we dive into Matthew chapter 20, verses 17 through 28.

Last week, we looked at a big chunk of text covering the rich young ruler, the disciples’ reward, and the laborers in the vineyard. The recurring theme running through all those passages was the radical difference of God’s kingdom. Today is really part two of that message. We are continuing to explore the significance of the Kingdom of God.

As we try to wrap our minds around what it means to live under the King’s rule and reign, we quickly realize we are not alone in our confusion. The twelve disciples were still trying to figure it out. They had not fully grasped it at all. When Jesus says things like, “The last shall be first and the first shall be last,” He is describing an economy that is completely upside down compared to anything we know. What we see in earthly kingdoms simply does not work as a template for what Jesus is establishing.

Our passage today breaks down into three distinct movements:

1. In verses 17–19, Christ speaks once again about His impending death in Jerusalem.
2. In verses 20–24, James and John bring their mother to ask Jesus for positions of highest honor and authority in His kingdom.
3. In verses 25–28, Jesus calls a timeout to reorient and recalibrate their entire understanding of kingdom greatness.

This whole passage functions like a giant funnel, narrowing down to the bedrock truth of verse 28. In Jesus’ kingdom, those in positions of authority and power use that power selflessly, not selfishly. If you have been granted influence or standing in Christ’s kingdom, it is never for your own personal advantage, but for the benefit of others.

The Sobering Reality of the Cross

Let’s begin by looking at Jesus’ private conversation with His disciples as they make their way toward Jerusalem.

Matthew 20:17-19 (NASB)

As Jesus was about to go up to Jerusalem, He took the twelve [disciples] aside by themselves, and on the way He said to them, ‘Behold, we are going up to Jerusalem; and the Son of Man will be delivered to the chief priests and scribes, and they will condemn Him to death, and will hand Him over to the Gentiles to mock and scourge and crucify [Him], and on the third day He will be raised up.’

Notice the intimacy in verse 17: Jesus pulls the twelve aside by themselves. He has critical information to share with them. This is at least the third time in Matthew’s Gospel that Jesus explicitly warns them of His destination. Luke tells us that Jesus “set His face toward Jerusalem.” He was locked in, laser-focused on His ultimate purpose. He did not come merely to perform miracles or gather crowds; He came with an unswerving mission.

In these verses, Jesus adds horrific new details they had not heard before. He tells them He will be delivered over, condemned to death, mocked, scourged, and crucified.

Two thousand years later, when we see a cross, we often associate it with love, grace, and redemption. But in the first century, the cross had only one association: brutal execution. To a first-century ear, hearing about crucifixion was like hearing someone say they were heading to the electric chair. It meant a agonizing, humiliating death reserved for criminals. Jesus presents this sobering, ominous reality to His closest followers just days before it will come to pass.

Missing the Point entirely

Right after Jesus lays out the harrowing details of His impending death, look at how the scene shifts in verses 20 through 24.

Matthew 20:20-21 (NASB)

Then the mother of the sons of Zebedee came to Jesus with her sons, bowing down and making a request of Him. And He said to her, ‘What do you wish?’ She said to Him, ‘Command that in Your kingdom these two sons of mine may sit one on Your right and one on Your left.’

James and John come with their mother to make a request. Mark tells us the brothers made the request, but Matthew reveals they brought mom along for a little extra leverage. She bows respectfully and asks that her two sons sit at Jesus’ right and left hand—the two highest places of honor and executive authority next to the King.

Think about the timing of this request. Jesus has just told them, “I am going to Jerusalem to be betrayed, mocked, beaten, and crucified.” And their immediate response is, “Hey, can we have the top executive seats when You take power?”

Talk about missing the point.

It reminds me of an upper-level sociology class I took in college. I bypassed the prerequisites because the catalog description sounded easy enough. The major grade for the semester was a massive 25-page research paper. I poured hours into that behemoth of a paper and turned it in. When I got it back, I flipped to the final page, and there in red ink was a zero.

I went straight to the professor’s office and said, “A zero? I wrote twenty-five pages! I could have cheated and gotten a zero!” He looked at me and said, “Mike, you wrote about something completely foreign to the assignment. You missed the point entirely.” He gave me an incomplete and let me redo it over the summer. I turned it in again, and he gave me a 60. He said, “Mike, you missed the point a second time!”

That is precisely where the disciples are. Luke 18:34 sheds light on their confusion:

Luke 18:34 (NASB)

But the disciples understood none of these things, and [the meaning of] this statement was hidden from them, and they did not comprehend the things that were said.

They could not comprehend what Jesus was saying. Perhaps they assumed His talk of death was metaphorical or hyperbolic. How could a kingdom exist with a dead king? They expected a political triumph, not an execution.

Jesus cuts straight through their misunderstanding in verse 22.

Matthew 20:22 (NASB)

But Jesus answered, ‘You do not know what you are asking. Are you able to drink the cup that I am about to drink?’ They said to Him, ‘We are able.’

Jesus pulls no punches: “You do not know what you are asking.” The “you” here is plural—in Texas, we would say, “Y’all don’t know what y’all are asking.” He is speaking directly to the brothers.

In the ancient world, drinking from a king’s cup symbolized intimacy, honor, and prominence. But the cup Jesus is about to drink is not a cup of royal luxury; it is the cup of divine wrath, suffering, and death.

We see this vividly in the Garden of Gethsemane when Jesus falls on His face and prays:

Matthew 26:39 (NASB)

And He went a little beyond [them], and fell on His face and prayed, saying, ‘My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.’

This imagery runs throughout the Old Testament as well. Psalm 11 describes fire, brimstone, and burning wind as the portion of the wicked’s cup. Isaiah 51:17 speaks of Jerusalem drinking the cup of the Lord’s anger. Jesus is asking, “Can you drink the cup of agony and suffering that I am about to drink?”

With utter confidence and blind ambition, they reply, “We are able.”

Matthew 20:23 (NASB)

He said to them, ‘My cup you shall drink; but to sit on My right and on [My] left, this is not Mine to give, but it is for those for whom it has been prepared by My Father.’

Jesus tells them they will indeed drink His cup. They would not receive instant prestige, but they would share in His suffering. History bears this out. James became the first of the twelve apostles to be martyred, executed by Herod Agrippa in Acts 12. John was the last surviving apostle, enduring brutal persecution and exile on the island of Patmos. From Peter to Bartholomew to Thaddeus, church history records that every single one of these men faced horrific martyrdom or exile for the name of Jesus Christ.

When the other ten disciples heard what James and John had done, verse 24 tells us they became indignant. This was not holy, righteous indignation; they were simply furious that the two brothers had tried to jump the line and secure the top spots before they could.

The Economy of Greatness

With tension boiling over among the twelve, Jesus calls a timeout.

Matthew 20:25-27 (NASB)

But Jesus called them to Himself and said, ’You know that the rulers of the Gentiles lord it over them, and [their] great men exercise authority over them. ’It is not this way among you, but whoever wishes to become great among you shall be your servant, and whoever wishes to be first among you shall be your slave;

For the second time in this passage, Jesus gently draws them near. He does not yell or use obscure parables; He speaks direct, clear truth.

He says, “You know how the Gentile rulers operate. Men like Caesar, Herod, and Pontius Pilate use their authority to dominate, manipulate, and leverage power for their own selfish gain. That is the world’s model.”

Then He delivers the radical kingdom standard: “It is not this way among you.”

If you want to be great in the Kingdom of God, you must become a servant (diakonos). Greatness is not about lording over others; it is about serving under them. And if you want to be first, you must become a slave (doulos)—a bondservant.

The concept of a bondservant carries profound Old Testament roots found in Deuteronomy 15. If an ancient Hebrew fell into destitute poverty, he could sell himself into the service of another Israelite for six years to work off his debt. In the seventh year, the master was commanded to release him freely and bless him generously from the flock, the threshing floor, and the wine vat.

Deuteronomy 15:16-17 (NASB)

’It shall come about if he says to you, ‘I will not go out from you,’ because he loves you and your household, since he fares well with you; then you shall take an awl and pierce it through his ear into the door, and he shall be your servant forever. Also you shall do likewise to your maidservant.

If the servant loved his master and his household, he could choose not to leave. To solidify this permanent relationship, the master would take an awl and pierce the servant’s earlobe into the doorpost. He became a bondservant for life—not out of compulsion, but out of deep love and devotion to a good master.

This is the very identity the Apostle Paul claims in Romans 1:1:

Romans 1:1 (NASB)

Paul, a bond-servant of Christ Jesus, called [as] an apostle, set apart for the gospel of God,

Paul, having been set free by the Gospel, willingly offers himself as a lifelong bondservant of King Jesus.

Galatians 2:20 (NASB)

’I have been crucified with Christ; and it is no longer I who live, but Christ lives in me; and the [life] which I now live in the flesh I live by faith in the Son of God, who loved me and gave Himself up for me.

Being a follower of Jesus means surrendering our perceived rights and handing our lives over to our Master. True greatness requires a fundamental shift in our mindset: we die to self so that we can live for Christ and serve others.

The Ultimate Ransom

Jesus brings the entire conversation to its ultimate, climactic point in verse 28.

Matthew 20:28 (NASB)

just as the Son of Man did not come to be served, but to serve, and to give His life a ransom for many.’

Jesus never asks His disciples to go anywhere He was not willing to go first. He embodies the heartbeat of His kingdom: power used completely selflessly. He stepped down from the glory of heaven not to be catered to, but to lay His life down as a ransom price for many.

This is the core of the Gospel. It is about giving our lives away. Everything we possess—our homes, our bank accounts, our time, our energy, our gifts—does not actually belong to us. We are simply stewards managing what belongs to God.

That truth can be hard to swallow. We work hard for our paychecks. We pay our mortgages and our utility bills. It naturally feels like our stuff. But the Gospel supersedes our earthly perspectives. As Psalm 50 reminds us, God owns the cattle on a thousand hills. Everything belongs to Him.

We stand in a long line of faithful men and women who embraced this bondservant posture. John the Baptist said, “He must increase, but I must decrease.” Paul spoke of being poured out like a drink offering. In Romans 12:1, he urges us to present our bodies as living and holy sacrifices.

Imagine spending your entire life desperately climbing the ladder of worldly success, only to reach the top and realize your ladder was leaning against the wrong building the whole time. What a tragedy. Jesus is recalibrating our hearts so we do not waste our lives on what does not last.

Following Jesus is not an easy road. There is a cup of sacrifice and self-denial that comes with walking in His footsteps. But it is the most glorious, worthy calling on earth.

If you have not yet surrendered your life to Christ, know that we will never offer you a watered-down gospel. Following Jesus will cost you your self-rule. But on the cross, Jesus paid the ultimate ransom for your sin that you could never pay on your own. Through His death and resurrection, you can be forgiven, made new, and welcomed into His eternal kingdom.

Look at how Paul sums up this selfless humility of Christ:

Philippians 2:5-11 (NASB)

Have this attitude in yourselves which was also in Christ Jesus, who, although He existed in the form of God, did not regard equality with God a thing to be grasped, but emptied Himself, taking the form of a bond-servant, [and] being made in the likeness of men. Being found in appearance as a man, He humbled Himself by becoming obedient to the point of death, even death on a cross. For this reason also, God highly exalted Him, and bestowed on Him the name which is above every name, so that at the name of Jesus EVERY KNEE WILL BOW, of those who are in heaven and on earth and under the earth, and that every tongue will confess that Jesus Christ is Lord, to the glory of God the Father.

Closing Prayer

Father, we rejoice in the reality that our Savior was willing to take the form of a bondservant and demonstrate what true humility looks like. He took that obedience all the way to the cross, willingly laying down His life for those He loved.

Lord, help us. We struggle with holding on to our own control, our own comfort, and our own status. Teach us what it truly means to live underneath Your rule and reign. Make us willing to drink the cup of self-denial and service. May we gladly live as bondservants of the King of kings and Lord of lords.

In Jesus’ name we pray, Amen.