Palm Sunday · Matthew 21:1-11 · Luke 19:28-44 · Zechariah 9:9 · Philippians 2:5-11

Palm Sunday Sermon: The King Who Weeps and Rides On

Palm Sunday sits at an odd angle in the calendar: the crowd's shout is real and the crowd is about to turn. A sermon here has to hold both the parade and the cross it walks toward, without letting either one cancel the other out.

The text at a glance

The crowd spreads cloaks and branches and quotes Psalm 118, reading Jesus through the lens of a coming king who will settle scores with Rome.
Jesus rides in on a colt, not a warhorse, enacting Zechariah 9:9 — a king who arrives in humility, already refusing the role the crowd is handing him.
Luke adds a detail Matthew does not: Jesus weeps over the city he is entering, because it does not know what makes for peace.
The same city that shouts hosanna on Sunday will call for crucifixion within days, and the text does not explain that reversal so much as let it sit.
Philippians 2 gives the theological account of what the crowd only half sees: this descent is not a detour from kingship but its shape, a self-emptying that precedes exaltation.

Three ways a sermon can go

The crowd's misreading

A sermon can trace what the crowd wanted from this king versus what they got, using the mismatch to ask what the congregation wants from Jesus now. This costs the preacher some comfort, since the honest answer is that most congregations still want a king who fixes their circumstances more than one who weeps over their city.

The king who weeps

Luke 19:41-44 lets a sermon sit with Jesus' grief over Jerusalem rather than move quickly to triumph. This requires slowing down at a verse many Palm Sunday sermons skip past on the way to the parade, and resisting the urge to resolve the grief too fast.

Humility as the shape of kingship

Reading Matthew or Luke alongside Philippians 2:5-11 lets a sermon show that the donkey is not incidental but definitional — this is what divine power looks like when it arrives. The cost is theological precision: the preacher has to say what kenosis means without turning it into a vague lesson about being humble.

Where sermons on this text commonly slip

Palm Sunday as pep rally

It is easy to preach the crowd's energy as pure celebration and stop there, especially with children waving branches in the aisle. That skips what the text itself flags — the crowd's hosanna is a request for rescue on their terms, and the king riding in is about to disappoint it.

Skipping the weeping verses

Luke 19:41-44 is easy to omit because it slows the momentum toward Easter and names Jerusalem's coming destruction, which requires more historical framing than a triumphal entry does. Leaving it out turns Palm Sunday into an uncomplicated victory lap the text does not support.

Treating the donkey as a footnote

Some sermons mention the colt only to prove Jesus fulfilled prophecy, as a citation, rather than reading it as Zechariah 9:9 intends — a deliberate statement about what kind of king this is. That turns a claim about the nature of God's power into a trivia fact.

Five questions to ask afterwards

Did the sermon quote or explain Zechariah 9:9 as more than a fulfilled-prophecy checkbox, or did it stay at prediction and fulfillment?
Did the sermon include Luke 19:41-44 (the weeping over Jerusalem), or did the transcript move straight from the entry to Holy Week without it?
Did the sermon name what the crowd wanted from Jesus, in a way distinct from what he actually did that day — check for two clearly stated, contrasting expectations?
If Philippians 2:5-11 was used, did the sermon connect the self-emptying language to the donkey and the crowd's misreading, or did it function as a separate, unconnected passage?
Did the sermon explain the shift from hosanna to crucify within days, or did it leave that turn unaddressed, as if the crowd's mood simply changed off-page?

Keeping the application on the ground

A landed application on this text names one place where the listener is treating Jesus as a king who should meet their terms, and asks them to bring one specific want to him honestly this week rather than managing it alone. A floating application just says welcome Jesus as king, which nobody can act on or fail to do.

Write down one outcome you are currently asking Jesus to deliver on your terms, and pray about it honestly before Wednesday, naming the terms out loud.
Read Luke 19:41-44 once a day this week and name one thing in your own city or neighborhood that grieves you the way Jerusalem grieved Jesus.
Before next Sunday, tell one person in your household or small group what kind of king you actually expect Jesus to be, and let them ask you a follow-up question.

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