The Upside-Down Kingdom: When Greatness Looks Like A Towel And A Cross Series

The Upside-Down Kingdom: When Greatness Looks Like a Towel and a Cross

Introduction — The Upside-Down Kingdom: When Everything Feels Backwards

There are moments in life when everything feels backwards.

What once seemed certain begins to shift.

What the world celebrates starts to feel hollow.

And deep within the heart, there is a quiet question: Is this really what greatness looks like?

Because we live in a world obsessed with greatness, we are living in a culture that celebrates visibility over virtue,

influence over integrity,

and power over humility.

Greatness is measured by followers, platforms, titles, influence, and control.

We are taught to climb, to compete, to secure our place at the top.

From a young age, we are shaped by a narrative that says: the higher you rise, the more you matter.

But when we come to Jesus…

everything turns upside down.

In the Kingdom of God, greatness does not look like a throne—it looks like a towel.

It does not look like domination—it looks like devotion.

It does not look like power—it looks like a cross.

And here is the tension we must feel this morning: the values we have absorbed from the world do not align with the values of Christ.

Our focus this morning is on the words Jesus speaks in Matthew 20:20-28, and we will also consider the parallel passages in Mark 10:35-45, Luke 22:24-27.

We will discover that Jesus is not offering a minor adjustment to our ambitions—He is calling for a complete transformation of our hearts.

He takes our definitions of success, leadership, and significance… and He turns them inside out.

Today, we sit at the feet of Jesus as He redefines greatness—not merely as a teaching, but as a way of life for every disciple.

And as we listen, we must be willing not only to admire His words… but to be changed by them.

Matthew 20:20-28 (NLT):

Jesus Teaches about Serving Others

20 Then the mother of James and John, the sons of Zebedee, came to Jesus with her sons. She knelt respectfully to ask a favour. 21 “What is your request?” He asked.

She replied, “In your Kingdom, please let my two sons sit in places of honor next to you, one on your right and the other on your left.”

22 But Jesus answered by saying to them, “You don’t know what you are asking! Are you able to drink from the bitter cup of suffering I am about to drink?”

“Oh yes,” they replied, “we are able!”

23 Jesus told them, “You will indeed drink from my bitter cup. But I have no right to say who will sit on my right or my left. My Father has prepared those places for the ones he has chosen.”

24 When the ten other disciples heard what James and John had asked, they were indignant. 25 But Jesus called them together and said, “You know that the rulers in this world lord it over their people, and officials flaunt their authority over those under them. 26 But among you it will be different. Whoever wants to be a leader among you must be your servant, 27 and whoever wants to be first among you must become your slave. 28 For even the Son of Man came not to be served but to serve others and to give his life as a ransom for many.”

1. The Misunderstood Kingdom — When Ambition Looks Spiritual

Matthew 20:20–21 (NLT): “Then the mother of James and John… asked, ‘In your Kingdom, please let my two sons sit in places of honour next to you…’”

This moment is striking. Jesus has just predicted His death (Matthew 20:17–19), and immediately—almost jarringly—the disciples are discussing status.

The request is not random—it reflects a deeply Jewish expectation of a Messianic Kingdom of power and prestige.

They believed Jesus would overthrow Rome.

They assumed positions of honour were up for grabs.

The Greek word for “honour” here (doxa) implies glory, prestige, visible greatness.

But notice this—they wanted the crown without the cross.

Jesus responds:

Matthew 20:22 (NLT): “You don’t know what you are asking! Are you able to drink from the bitter cup of suffering…?”

The “cup” (Greek: poterion) is a powerful Old Testament image of divine suffering and judgment (Isaiah 51:17).

Jesus is saying: “You’re asking for glory—but do you understand the cost?”

How often do we do the same?

We want influence—but not sacrifice.

We want recognition—but not surrender.

We want the platform—but not the pain.

Friends, discipleship is not about climbing into prominence—it is about dying to self.

Tim Keller wrote: “The way up is down. The way to become rich is to give all your money away. The way to power is to serve.”

Keller captures what Jesus is teaching—this Kingdom runs on a completely different engine. The world says, “assert yourself.” Jesus says, “deny yourself.” And only one of those paths leads to life.