Today we’re in Matthew 11:2–11, and I want you to picture one simple image:
A small prison window.
On one side of that window is John the Baptist – chained, confined, waiting. On the other side is Jesus – healing, preaching, raising the dead, announcing good news to the poor.
And between them, carried by a handful of disciples, is one honest, painful question:
“Are you the one who is to come, or should we look for another?”
If you’ve ever loved Jesus and still wondered where He is, this text is for you.
John’s Situation: From Wilderness to Fortress
Let’s set the scene.
John the Baptist used to stand under open skies in the wilderness, calling Israel to repentance. Crowds came. Tax collectors, soldiers, religious leaders – they all heard him. He baptized in the Jordan and pointed at Jesus with confidence: “Behold, the Lamb of God.”
But by Matthew 11, John’s address has changed.
He has confronted Herod Antipas over an immoral marriage, and Herod has responded the way powerful people often do when the truth hits too close: he locked John up. Historical sources point to Machaerus, a desert fortress perched above deep ravines, where political prisoners could be held and forgotten.
So imagine John:
No crowds, no river, no open horizon.
Just stone walls, a narrow slit of a window, and whatever scraps of news his disciples bring.
They tell him about Jesus – the healings, the sermons, the crowds. And John begins to think:
“If the kingdom has really arrived… why am I still here?
Why is Herod still on the throne?
Where’s the fire I preached about?”
That tension between what he expected and what he sees from his tiny window is what produces the question he sends to Jesus.
The Question We’re Afraid to Ask
Listen again to John’s words:
“Are you the one who is to come, or should we look for another?”
This is not a skeptic’s jab from the sidelines. This is the question of a believer in chains.
John has history with Jesus. He has seen the Spirit descend at Jesus’ baptism. He has staked his whole ministry on preparing the way. But prison has a way of shrinking your world and amplifying your doubts.
Some of you know that feeling.
You’ve walked with Jesus for years. You’ve believed, taught, maybe even preached. And then something happens:
A diagnosis.
A betrayal.
A door that doesn’t open.
And suddenly your prayers sound less like, “Here I am, Lord,” and more like, “Are You really who I thought You were?”
Matthew does something very pastoral here: he lets the greatest prophet of the old era ask the question many of us are afraid to voice. That, by itself, is good news.
Jesus’ Answer: Look Through a Different Window
How does Jesus respond?
He does not send back a quick “Yes.”
He also doesn’t say, “How dare John doubt.”
Instead, He says to John’s disciples:
“Go and tell John what you hear and see.”
And then He lists it:
The blind are receiving their sight.
The lame are walking.
Those with leprosy are being cleansed.
The deaf are hearing.
The dead are being raised.
The poor are hearing good news.
If you know the prophets, you hear the resonance. Jesus is pulling language from Isaiah – places where God’s coming is described with exactly these kinds of images: blind eyes opened, lame legs leaping, good news proclaimed to the poor and captives.
In other words, Jesus is saying:
“John, I am doing what the Scriptures said Messiah would do. The kingdom is already here. It just doesn’t look like the judgment-first script you expected.”
Then He adds a beatitude we don’t quote often:
“Blessed is the one who does not stumble on account of me.”
Blessed is the one who doesn’t trip over a Messiah who heals before He judges, who restores before He overturns, who goes to the poor before He goes to the palace.
For John – and for us – Jesus is inviting a different way of seeing:
“Your prison window is small. Let Me widen your view.”
Jesus Talks About John: Honor in the Midst of Doubt
As John’s disciples walk away, Jesus turns to the crowd and starts talking about John.
“What did you go out into the wilderness to see?” He asks. “A reed shaken by the wind? A man in soft clothes? No – you went to see a prophet… and more than a prophet.”
He quotes Malachi: John is the messenger sent ahead to prepare the way. And then Jesus says:
“Among those born of women, no one has arisen greater than John… yet the least in the kingdom of heaven is greater than he.”
Here’s the beauty: Jesus is honoring John while John is questioning Jesus.
He doesn’t define John by his moment of confusion. He doesn’t say, “Well, if he really trusted Me, he wouldn’t be asking.” No – He upholds John’s calling, even as John wrestles to understand Jesus’ calling.
That is stunning grace.
If you are listening today with your own questions, hear this:
Jesus is not waiting to see if you doubt before deciding whether you matter. Your questions don’t erase your history with Him.
Bringing It Home: Our Prison Windows
So what does this sound like for us?
First, it gives us permission to bring our doubts to Jesus instead of letting them fester in the dark.
John could have sat in his cell and stewed in silence. Instead, he sends his disciples with an honest question. That is a faithful act.
Maybe your “prison window” is a chronic illness, a strained marriage, a financial trap, or just the quiet weight of anxiety. What would it look like to turn that into a place where questions are sent to Jesus, not hidden from Him?
Second, it calls us to look for Jesus’ Isaiah-shaped work even when our circumstances haven’t changed.
Sometimes we say, “God hasn’t done anything,” when what we mean is, “God hasn’t done the one thing I wanted in the way I imagined.” Meanwhile, around us and even in us, eyes are being opened, hearts softened, sins forgiven, and the poor cared for.
Jesus’ answer to John is essentially, “Pay attention to the actual signs of the kingdom, not just to the bars in front of you.”
Third, it quietly redefines greatness.
John is the greatest of the prophets, yet the least in the kingdom is greater. Translation: the smallest, most ordinary disciple of Jesus – who lives on this side of the cross and resurrection – stands in a place of privilege and nearness to Christ that John himself longed for.
So yes, your life may feel small. You may be changing diapers, answering emails, sitting in waiting rooms. But if you belong to Jesus, you are already part of the kingdom John announced. In God’s eyes, that is greatness.
Closing and Blessing
As we close, I want you to imagine again that little prison window.
On one side, John with his questions.
On the other, Jesus with His Isaian signs of the kingdom.
Some of you are listening from your own “cell” today. You love Christ, but the door has not opened yet. You are tired of waiting, tired of not understanding.
Hear the Gospel in this text:
Your questions are not too much for Jesus.
His work is often deeper and wider than your window can capture.
And in His kingdom, even the least – even you, in your smallness and confusion – can be called “greater” because you belong to Him.
Let me speak a simple blessing over you:
May the Lord who met John in his prison
meet you in yours.
May He widen your window
to see the quiet signs of His kingdom.
And may you find yourself, again and again,
trusting the real Jesus,
even when He refuses to fit your expectations.
Thanks for listening.
Go in peace, and in the hope of the One who really is to come –
and who has already come.
