The Tragedy and Triumph of Palm Sunday

Palm Sunday is more than a cheerful celebration—it’s a collision of tragedy and triumph that invites us to ask: Am I following Jesus or fighting against Him?

📷:Tim Mossholder

We live in a culture that loves to celebrate—but often struggles to truly understand the meaning behind our celebrations.

Think about it…

We throw backyard barbecues on Memorial Day, but how often do we actually stop to honor the lives laid down in service to our country? We wear green and pinch each other on St. Patrick’s Day without knowing the story of a young missionary who returned to the very people who once enslaved him, just to tell them about Jesus. Even Christmas and Easter—days at the very center of our faith—can get buried beneath shopping lists, traditions, and busy schedules.

We love to celebrate. We’re just not always clear on what, or why we’re celebrating.

And honestly, Christians aren’t immune to this.

We are fresh off Palm Sunday here at the start of this Holy Week.

Often, we reduce this story to a cheerful scene: a donkey, palm branches, smiling crowds. But the real Palm Sunday was far more complex. It was a day woven with both tragedy and triumph, and it presses us to examine the posture of our own hearts.

The story brings us to a simple but significant truth:

I am either following Jesus or fighting against Him.

Let’s walk slowly through Luke’s account and let the story shape us.

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Jesus Was Determined to Complete His Mission

“After Jesus had said this, He went on ahead, going up to Jerusalem.”

(Luke 19:28, CSB)

At first glance, Luke’s words might feel like a simple transition. But there’s something deeper happening. Every deliberate step Jesus took toward Jerusalem brought Him closer to suffering.

Earlier in Luke’s Gospel we read, “When the days were coming to a close for him to be taken up, he determined to journey to Jerusalem.” (Luke 9:51, CSB)

Jesus wasn’t drifting toward His death. He was determined. This wasn’t fate. It wasn’t a tragic accident. He didn’t move toward Jerusalem expecting a party. He moved toward it anticipating a cross.

One of the things that has brought me the most joy the past couple of years has been watching Ryder learn to skate. One of the things I admire about him the most is his determination. Skateboarding is all about progression. You’re always learning some new trick or some new skill. Which kind of means you’re always failing at something. And failing on a skateboard often means falling. So it requires immense resilience. And over and over again I’ve watched Ryder lock in, drive through failure, get up from every fall, and keep progressing forward. It’s been a powerful display of determination.

How much more should we be moved by the determination of Jesus, pressing forward in love, even as the shadow of the cross lengthened before Him?

In Gethsemane, His prayer revealed His heart: “Father, if you are willing, take this cup away from me—nevertheless, not my will, but yours, be done.” (Luke 22:42, CSB)

Every step He took was a step for you and for me.

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Jesus Was in Control of Every Detail

As they neared Jerusalem, Jesus sent two of His disciples to secure a young colt. He even anticipated the questions they would face from its owners.

Now, whether Jesus prearranged this or not, picture the moment:

If someone climbed into your car and said, “The Lord needs it,” your response would be, “Tell the Lord to get His own car!”

But the truth is, this wasn’t theft, nor some Jedi mind trick. It was a recognized custom in the first-century Near East called angaria—where officials or religious leaders could legally request property or service. And when the disciples said, “The Lord needs it,” it wasn’t just a request. It was a royal claim.

More importantly, it shows us something vital:

Jesus wasn’t improvising.

Every step was deliberate.

Luke emphasizes the tying and untying of the colt five times, driving home the point—nothing here was by accident.

Over and over Luke works to remind us that Jesus was not dragged to the cross. He chose it.

Jesus said in John 10:18, “No one takes [my life] from me, but I lay it down on my own.”

The cross wasn’t evil triumphing over good.

It was love triumphing over sin.

Even in the ordinary detail of a borrowed colt, Jesus’ sovereign power was at work.

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Jesus Was Committed to Fulfilling Scripture

When Jesus rode into Jerusalem, He wasn’t just making a grand entrance—He was fulfilling a centuries-old prophecy:

“Rejoice greatly, Daughter Zion! Shout in triumph, Daughter Jerusalem! Look, your King is coming to you; he is righteous and victorious, humble and riding on a donkey, on a colt, the foal of a donkey.”

(Zechariah 9:9, CSB)

Sometimes we imagine this moment like a modern-day championship parade—like when a million fans flooded the streets of Philadelphia after the Eagles’ Super Bowl win earlier this year.

But Luke tells us this was “the whole crowd of the disciples.” It wasn’t the whole city. It was probably at most a few hundred people. But the event was far bigger than the size of the crowd.

The disciples laid their cloaks on the road, providing Jesus with a royal welcome. They waved palm branches as a symbol of victory and hope. They shouted, “Blessed is the King who comes in the name of the Lord!” (Psalm 118:26)

It all looked like a victory parade. And in many ways, it was.

But they also misunderstood the victory Jesus was bringing.

They wanted a king to overthrow Rome.

Jesus came to overthrow sin and death.

His throne would not be gold, but wood.

His crown would not be jeweled, but thorned.

Triumph and tragedy were woven together in every step.

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Two Responses: Follow or Fight

Despite the celebratory tone of this event, not everyone was excited.

Some Pharisees, hearing the worship of Jesus, demanded He rebuke His disciples.

Now, try to see it from their side.

If someone walked into your church and people started worshiping them, you’d probably say, “Hey, maybe tap the brakes a bit!”

But their response revealed something deeper.

They weren’t protecting the faith. They were resisting the One the faith had been preparing them for.

This should serve as a sobering reminder to you and I. Religious pride can be subtle and deadly.

When we trust in tradition, performance, or personal goodness instead of Jesus, we can easily find ourselves standing in opposition to Him without even realizing it.

Jesus refused to silence His disciples.

He said, “I tell you, if they were to keep silent, the stones would cry out.” (Luke 19:40, CSB)

Even creation knows its King—and it will not stay silent.

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Will We Follow or Fight?

Palm Sunday is a collision of tragedy and triumph.

The King comes—not with a sword, but with open, welcoming hands.

Not to take power, but to lay His life down.

And the shadow of the cross falls across every moment of this day.

As we begin Holy Week, the question isn’t whether Jesus is King.

The question is: Will we respond to Him as King?

Will we follow Jesus in humble trust?

Or fight against Him in prideful resistance?

This week, I’m praying we slow down:

That we sit in the silence of Good Friday.

That we embrace the ache of Holy Saturday.

And that we rise to celebrate the triumph of resurrection on Easter Sunday.

But it all starts here—with one simple, searching question:

Am I following Jesus—or fighting against Him?

The King has come.

The cross stands before Him.

And the choice stands before us.

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Before you rush into the rest of your day, take a moment: Where do you see yourself in this story? Following or fighting? I’d love to hear what stood out to you—feel free to share in the comments.