Looking Through the Eyes of Jesus Matthew 21:1–11Palm Sunday A Reflections in Conversation with Henri Nouwen's, "Can You Drink This Cup?"

INTRODUCTION

Just one chapter before the palms are cut and the cloaks are spread on the road, there is a quieter, sharper exchange. A mother approaches Jesus on behalf of her two sons. She wants thrones — one on the left, one on the right. Jesus turns to the sons and asks them a question that re-frames everything: Can you drink the cup I am going to drink?

Henri Nouwen, writing near the end of his own life, called this the great spiritual question. Can you drink this cup? Not just the cup of privilege or blessing — but the whole cup. The cup that holds sorrow as well as joy, suffering as well as celebration, the cost of love alongside the gift of it. Can you drink the life God has given you, all of it, to the dregs?

One chapter later, Jesus climbs on a donkey and rides into Jerusalem. The crowd cries Hosanna — save us, we pray. And what we see is not a king who has avoided the cup, but a king who is already drinking it. Every step toward Jerusalem is a step deeper into what the cup holds. Looking through the eyes of Jesus on Palm Sunday means looking through the eyes of someone who has said yes to the cup — and who rides gently, humbly, into the fullness of what that yes will cost.

Nouwen gives us three movements for understanding the cup: holding it, lifting it, and drinking it. These three movements illuminate everything that is happening in Matthew 21. They also illuminate everything that is asked of us.

I. HOLDING THE CUP — THE HUMILITY OF THE DONKEY

Nouwen says that holding the cup is the first and most basic spiritual act. Before you can lift the cup or drink from it, you have to be willing to hold it — to look honestly at what is inside. To hold the cup is to evaluate your life with both humility and courage. It means looking clearly at the sorrow and the joy that fill it, without flinching from either. And it means recognizing that the cup of your life is not yours alone — it has been shaped by others, filled by others, and offered to others.

Watch how Jesus holds the cup as he approaches Jerusalem. He sends two disciples ahead with very specific instructions. They are to find a donkey and a colt — animals that have been arranged in advance, as if Jesus has already surveyed the terrain and made his peace with it. He knows what is coming. The passion predictions in chapters 16, 17, and 20 have made it plain. He will be handed over, condemned, mocked, flogged, and crucified. He holds all of that in his hands as he descends the Mount of Olives.

And the cup he holds is full of both. It is full of sorrow — the cross is ahead, the betrayal is ahead, the abandonment of the disciples is ahead. But it is also full of joy — this crowd, these cloaks on the road, these branches cut from trees, these voices shouting the ancient words of Psalm 118. Nouwen is careful to say that the cup of life holds both sorrow and joy together, and that we cannot hold one without the other. To hold only the joy is sentimentality. To hold only the sorrow is despair. Jesus holds both. That is why he can ride so calmly, so gently, on a donkey toward a city that will reject him.

The Greek word Matthew uses for Jesus' character here — praus, meek or gentle — is not the word for passivity. It is the word for a strength that has been tempered, a power that has been placed in service. Jesus is not passive on the way into Jerusalem. He is fully present, fully clear-eyed, holding his life with both hands and refusing to let the weight of it make him either bitter or afraid.

For us, holding the cup means this: before we can worship truthfully, we have to be willing to be honest about the cup we carry. Not just the polished parts we bring to church on Sunday, but the full contents — the grief we have not named, the joy we have not claimed, the life we are still learning to accept as the life God has actually given us, rather than the life we had planned. Palm Sunday begins with holding. You cannot wave a branch with both hands if one hand is clenched tight around a life you refuse to examine.

II. LIFTING THE CUP — HOSANNA AS EUCHARISTIC GESTURE 

The Cup of Salvation

Nouwen's second movement is lifting — and here the imagery becomes explicitly Eucharistic. To lift the cup is to offer it, to hold it up in the presence of others, to say: this is my life, and I offer it in gratitude and in hope. Nouwen describes the lifting of the cup as a kind of toast — a declaration that life, even in its suffering, is worth celebrating. It is an act of transparency, of sharing not just the successes but the trials, and inviting others to do the same.

Listen again to what the crowd shouts as Jesus lifts — as it were — his entrance into the city. Hosanna. In Hebrew, hoshia na: save us, we pray. This is taken from Psalm 118:25-26, a psalm sung at Passover, when the community gathered to remember that God had heard their cry in Egypt and led them out through water and wilderness. To shout Hosanna is not simply to praise. It is to lift your need — your real need, your community's real need — before God and say: we are here. We are desperate. And we trust that you hear us.

This is the gesture of lifting. The crowd on the road is not performing for an audience. They are doing something deeply communal and deeply vulnerable. They are spreading their cloaks — the coats off their backs — because they believe this moment calls for everything they have. They are cutting branches from trees and laying them in the road because they are trying, with the materials available to them, to honor what they sense is holy. And they are lifting their voices in a song that is both celebration and petition at once.

Nouwen writes that lifting the cup together is what community is for. You cannot lift a cup alone — or rather, lifting it alone misses the point. The cup is lifted in the presence of others, and in lifting it, you affirm them: your life matters, your cup matters, what is inside it — your joy and your sorrow together — is worth honoring. This is why the Palm Sunday procession is communal. It is not a private spiritual exercise. It is the people of God moving together, lifting together, saying together: Blessed is he who comes in the name of the Lord. There is something here for how we worship. Authentic worship is not performance — not lifting a polished version of ourselves before God and pretending the cup is only full of good things. 

In the blockbuster movie, Indiana Jones and the Last Crusade, the plot of the movie is around the search by the Nazi’s to find the cup of the Last Supper. They thought that if they found the cup and drank from it, they would have eternal life. In a climactic, most important scene, they found the cup, but surrounded by a table full of other cups, guarded by a very old knight. Choose the wrong cup, and you die. The hero, Indiana Jones, was captured by the Nazi’s, watched as the bad guy chose the most beautiful cup on the table, one fit for a king! When the Nazi drank from the cup, something happened; instead of immortal life, he died a terrible death. The knight guarding the cup stated, “He chose poorly.” Then, our hero, Indiana, turns to drink from the cup. He looked and looked and found the ugliest and simplest of all cups, and drank from it. The knight stated, “You chose wisely.” 

Hosanna (hoshia na, "save us, we pray") is not praise but a cry of need, and I will add, I cry to help others. We not only receive salvation of whatever is going on in our lives, but also salvation for communion, toward others, it is never an end in itself. The crowd is right to cry for deliverance; they just can't yet see how deep salvation goes.

Authentic living, authentic worship, is lifting the actual cup, the real cup, with all of its content and fullness of life, saying to God and to one another: “Lord, I want to drink this cup. A cup that contains a life filled with love, to give love, with all of its sorrows and joys.” Can we drink that cup? 

III. DRINKING THE CUP — THE COST AND GIFT OF FOLLOWING

First, we choose the cup; then we hold it; and now, the final movement is the hardest. Nouwen says that drinking the cup — drinking it to the dregs—is the culmination of everything that came before. It is the full acceptance of the life God has given: not a partial acceptance, not a careful sipping that avoids the bitter parts, but the whole thing. Drinking to the dregs becomes, in a sense, our salvation. It is what Paul means in Philippians 2:12 when he urges us to work out our salvation with fear and trembling — not to earn it, but to live into it fully, to let it reach every part of us.

Jesus is drinking the cup as he rides into Jerusalem. Every step the donkey takes is a step deeper into what the cup holds. The city ahead will receive him with branches and Hosanna chants, and on Friday, reject him with a cross. The disciples who are shouting Hosanna will be asleep in Gethsemane by Thursday. And Jesus knows all of this. The passion predictions have been explicit. He is not surprised. He is not fleeing. He is riding directly toward it, gently, on a borrowed animal, with the crowd pressing close around him.

Nouwen draws on his years at L'Arche Daybreak in Toronto — a community of people with and without intellectual disabilities — to illustrate what drinking the cup looks like in practice. He describes watching the community gather for Eucharist, watching people who by the world's standards have been handed cups no one would choose, and seeing them drink those cups with a grace that dismantled his assumptions about suffering and joy. The people the world calls least were teaching him what it means to live fully, to accept the life actually given rather than the life imagined.

This is what the Palm Sunday crowd does not yet understand. James and John's mother has just asked for thrones. The crowd is shouting for a king who will overthrow Rome. They want a cup that holds only victory. But Jesus is riding toward a cup that holds betrayal and abandonment and death — and through all of it, resurrection. The disciples will only understand this later. The drinking comes before the understanding. You live into the truth of the cup; you do not reason your way into it first.

For us, drinking the cup means this: we are called not to a managed Christianity, a careful religion that takes the parts we like and leaves the rest. We are called to the whole life. The cup holds our losses — the relationships that did not survive, the dreams that were surrendered, the grief that still lives in the body. And it holds our joys — the moment a child's face opens into laughter, the unexpected kindness of a stranger, the inexplicable sense that we are held. Drinking the cup means accepting all of it as the life through which God is working.

And crucially — as Nouwen insists and as this text makes plain — we do not drink alone. The crowd on the road is not a collection of isolated individuals. They are a community in motion, moving together toward something they cannot yet fully see but trust enough to follow. To drink the cup is to drink it in community, to walk the road together, to let the suffering of others inform and deepen our own, and to carry each other when the cup feels too heavy to lift alone.

IV. THE QUESTION JESUS ASKS US

Can you drink this cup?

Jesus asked this of James and John. He asks it of us. And the answer is not a one-time declaration. It is a daily practice, a liturgical rhythm, a return again and again to the cup that holds your actual life and the willingness to hold it, lift it, and drink it in his name.

Palm Sunday is the beginning of Holy Week precisely because the week ahead is the cup in its fullest form. We wave branches today and by Thursday we will be in the garden. By Friday we will be at the foot of the cross. The journey from Hosanna to the empty tomb runs directly through holding, lifting, and drinking — through the full cost of love and the full gift of resurrection.

What makes the entry into Jerusalem so luminous is not the crowd or the branches or even the shout of Hosanna. It is the person at the center — the one riding gently on a donkey, who has already said yes to the cup, who is already drinking it, who looks out at Jerusalem with eyes full of grief and love and says: I see what is in this city. I see the rejection ahead. I see the cross. And I am riding toward it anyway, because the cup that holds all of this also holds the resurrection. And the resurrection is worth everything the cup costs.

That is what it means to look through the eyes of Jesus. To see clearly. To hold honestly. To lift together. To drink fully.

CONCLUSION

Nouwen ends his book not with resolution but with invitation. The cup is not finished. There is always more to drink, always more life to accept, always more grace to receive. But the invitation is real: Come. Hold this cup. Lift it with your brothers and sisters. Drink it to the remains, drink it to the last sediment of sour taste.

On this Palm Sunday, Jesus rides toward us on a donkey. He has already said yes to his cup. He invites us to say yes to ours — not to the cup of our choosing, but to the cup of our actual lives, held in his hands, lifted in community, drunk in the faith that the God who asks Can you drink this cup? has already drunk it first.

The crowd shouted Hosanna — save us, we pray.

He answered. He is still answering. And he asks us: Can you drink this cup?

By God's grace — we can.

Amen.