When the Courage of Men Fails
This is the manuscript of the Matthew 26:30-35, 69-75 sermon I preached on October 19, 2025 at Trinity West Seattle as part of our Upside Down Kingdom sermon series through the Gospel of Matthew.
You can watch it here or read it below.
SERIES INTRO
We’re in a sermon series in the Gospel of Matthew called the Upside Down Kingdom. We called it that because it’s about the kingdom of heaven—Jesus’ kingdom—coming to earth. And heaven coming down to earth is upside down from the ways we’re used to. But in reality, the Upside Down Kingdom is the way things ought to be in the world. Through this series, my hope and prayer is that we will grow as Upside Down Kingdom people, that by God’s working in and through us, the earth would be one step closer to heaven.
Let’s pray.
SERMON INTRO
In our text today we get to experience something unique. Matthew actually takes the camera off of Jesus and points it at the leader of the disciples, Peter.
During the passion narrative (Jesus’ journey toward death), Matthew only does this for two characters: Peter and for Judas. And he does so for a very specific reason: to show the different responses to Jesus the Messiah.
Today, we get to focus on Peter. So today, as we read in the text, we are looking at the Passover evening and end up with the actual events of Peter’s denial...when we see his courage fail. Though, we do need a little backstory.
Let’s get to know Peter a little better as we move toward our moments in the text today. We’re going to do this together through four movements.
Peter’s Backstory
Peter’s Confidence
Peter’s Denial
Peter’s Tears
There is something special for us in each of these four movements, but the big idea we will land on today is the following: When we realize how far off we are, trust in the One who drew near to us.
Because Peter thought he was doing pretty good…then all of a sudden he wasn’t.
PETER’S BACKSTORY
We first meet Peter in the Gospel of Matthew in chapter 4:18-20. Jesus withdrew to Galilee after John the Baptist's arrest and called his first disciples.
Simon, later called Peter, first met Jesus at the Sea of Galilee. Peter follows Jesus immeidately…no hesitation. Peter is bold, impulsive, takes risks, follows his heart. He’s the first to move.
Jesus continues about his ministry of teaching and healing, Peter is there for it. He is eventually commissioned by Jesus in Matthew Chapter 10. Check this out:
Matthew 10:1–2a
[1] And he called to him his twelve disciples and gave them authority over unclean spirits, to cast them out, and to heal every disease and every affliction. [2] The names of the twelve apostles are these: first, Simon, who is called Peter…
Peter is mentioned first in every list of Disciples in the New Testament (Mt 10, Mk 3, Lk 6, Ac 1). He is the face of the twelve disciples. He is in Jesus’ inner circle. Peter is always first. The first to follow. And usually the first to speak or act. Peter is a natural leader.
A few chapters later, the disciples see someone (Jesus) walking on the water from their boat and Peter calls out…
Matthew 14:28–30
[28] And Peter answered him, “Lord, if it is you, command me to come to you on the water.” [29] He said, “Come.” So Peter got out of the boat and walked on the water and came to Jesus. [30] But when he saw the wind, he was afraid, and beginning to sink he cried out, “Lord, save me.”
Jesus grabs him, calms the storm. Peter…No fear. Courageous, a bit impulsive. At his best, he’s focused on Christ and he. Walks. On. Water.
But when did Peter begin to sink?
[30] When he saw the wind, he was afraid, and beginning to sink he cried out, “Lord, save me.”
When he took his focus off of Christ, his courage failed. Peter had many moments like this throughout Matthew and the other gospels. Bold, daring, courageous…but also distracted and impetuous, vacillating between human frailty and divine empowerment.
But Matthew chapter 16, might be the clearest insight into Peter. In Matthew 16:13-23 we have two paragraphs that sum up all of who Simon Peter really is.
Matthew 16:15–16
[Jesus] said to them, “But who do you say that I am?”
Simon Peter replied, “You are the Christ, the Son of the living God.”
Peter boldly declares Jesus to be the Christ, Son of living God. And Jesus goes on to call Peter blessed! But that exact same boldness gets him in trouble mere moments later.
Matthew 16:21–23
[21] From that time Jesus began to show his disciples that he must go to Jerusalem and suffer many things from the elders and chief priests and scribes, and be killed, and on the third day be raised. [22] And Peter took him aside and began to rebuke him, saying, “Far be it from you, Lord! This shall never happen to you.” [23] But he turned and said to Peter, “Get behind me, Satan! You are a hindrance to me. For you are not setting your mind on the things of God, but on the things of man.”
Peter rebuked Jesus! He just calls him the Son of God and turns around and tries to correct Jesus! “Get behind me Satan! You are a hindrance to me.” What a scathing rebuke…
…but look at the sentence right afterward:”For you are not setting your mind on the things of God, but on the things of man.”
That sentence describes Peter perfectly. When Peter sets his mind on things of God, nothing can stand against him. He walks on water. He drops his net and pushes forth the kingdom of God. But when he focuses on things of man…his own circumstances…his own expectations and perspectives…the waves and winds around him…he sinks. Things start to crumble quickly.
Maybe you have noticed this in your own life. When we take our eyes off of Christ, the world becomes overwhelming. Maybe you start to act as if God isn’t really there, and do your own thing. That might work for a minute…but it will always end with us crying out, “Lord, save me!”
PETER’S CONFIDENCE
That brings us to the night of Passover. We have covered some of this in previous weeks. But given what we have covered with Peter so far, put yourself back at the Passover night there with Peter for a second.
Dinner is over, your stomach is full. Jesus just talked about betrayal. He also talked about his body and blood. You are probably a bit confused, but used to Jesus talking this way at this point. Then you sing a hymn together, and go up to the Mount of Olives. Jesus says something else that causes Peter to jump in with some bold words.
Matthew 26:30–35
[30] And when they had sung a hymn, they went out to the Mount of Olives. [31] Then Jesus said to them, “You will all fall away because of me this night. For it is written, ‘I will strike the shepherd, and the sheep of the flock will be scattered.’ [32] But after I am raised up, I will go before you to Galilee.” [33] Peter answered him, “Though they all fall away because of you, I will never fall away.” [34] Jesus said to him, “Truly, I tell you, this very night, before the rooster crows, you will deny me three times.” [35] Peter said to him, “Even if I must die with you, I will not deny you!” And all the disciples said the same.
Peter contradicts Jesus first, then DOUBLES DOWN…and others follow his lead. I mean, you have to admire Peter’s confidence levels here. He is so confident that all the disciples agree and say the same. Peter is a leader.
But he misses the part about Jesus being raised up and meeting up in Galilee. Imagine what Jesus must be feeling in that moment. He knows what is coming. He just saw Judas go away to betray him. No Peter is missing the point…AGAIN. What must Jesus have felt in these moments?
Jesus just talked about his body being broken and his blood being shed, so the forthcoming physical anguish and torture is on his mind. Then he says all his friends will scatter like sheep when a shepherd is struck.
So in the midst of the physical torture, Jesus will simultaneously experience the horror of abandonment. And Peter doesn’t listen, he doubles down and says, “Even if I must die with you, I will not deny you!”
Peter’s intentions are noble and courageous, but those of us who are familiar with the story know the impact…empty. Void. Cowardly. Self-protecting.
As we move from Jesus’ foretelling toward the denial moment…let’s briefly look at what happens with Peter.
Jesus is praying in the garden, and Peter can’t even stay awake! Three times Jesus tries to keep Peter and others awake. They just can’t do it. Can you imagine the anguish Jesus must be experiencing? Where is Peter’s zeal and courage at this moment?
Then Judas shows up again, with “a great crowd with swords and clubs, from the chief priests and the elders of the people”. Judas betrays his friend with a kiss. Then a disciple strikes the high priest's servant with a sword. Cuts off his ear.
The gospel of John identifies Peter as the one swinging the sword. Peter…always the first to speak or act. Courageous or impulsive? Jesus stops the confrontation, heals Malchus’ ear (Lk 22), then is arrested.
Matthew 26:56b–58
[56b] Then all the disciples left him and fled.
[57] Then those who had seized Jesus led him to Caiaphas the high priest, where the scribes and the elders had gathered. [58] And Peter was following him at a distance, as far as the courtyard of the high priest, and going inside he sat with the guards to see the end.
The striking of the shepherd has begun and the sheep are starting to scatter…but Peter follows this arresting party at a distance…and he follows straight into the high priest's courtyard. Peter sat with the guards. He is bold, I'll give him that. Maybe Peter is hiding in the crowd trying to avoid the ones he encountered in the garden. Peter is there to see the end. Now what end does he see is this kangaroo court? What was their verdict?
Matthew 26:66–68
[66]...“He deserves death.” [67] Then they spit in his face and struck him. And some slapped him, [68] saying, “Prophesy to us, you Christ! Who is it that struck you?”
The Shepherd has been struck. What will Peter do?
PETER’S DENIAL
Matthew 26:69a
Now Peter was sitting outside in the courtyard.
He hears Jesus publicly reveal himself as the Messiah to the high priests...and it did NOT go well. The authorities that Peter has revered and followed his whole life erupt with cries of blasphemy and calls for death. They beat Peter’s teacher and friend.
Peter witnesses Jesus, this man he loved, his Lord, his friend, the teacher he dedicated his last few years to following, the man who got Peter to drop his fisherman’s nets and follow…he watches Jesus get condemned to death.
Can you imagine the questions going through Peter’s mind? The fear bubbling underneath the surface? Someone, a servant girl, breaks his contemplative state and fearful ponderings with a comment.
Matthew 26:69b-70
And a servant girl came up to him and said, “You also were with Jesus the Galilean.” [70] But he denied it before them all, saying, “I do not know what you mean.”
The first denial. Peter is outed. He can’t hide in the crowd anymore. He is being publicly associated with the man just condemned to death. His fear is palpable. His safety is at risk. So he protects himself, “I don’t know what you mean.” Flight is on his mind and he begins to physically distance himself from the scene. Trying to squeeze through the crowd to get away.
Matthew 26:71–72
[71] And when he went out to the entrance, another servant girl saw him, and she said to the bystanders, “This man was with Jesus of Nazareth.” [72] And again he denied it with an oath: “I do not know the man.”
The second denial. Peter is able to get to the entrance of the courtyard, extending the distance between him and the accused. But Peter is exposed by another servant. He might be sweating from the emotions and fear swirling around inside of him. Is his life on the line too? But he finds it within himself to swear an oath to all those who just watched a man be condemned to death. He denies that he knew Jesus, “I do not know the man.”
Matthew 26:73–75
[73] After a little while the bystanders came up and said to Peter, “Certainly you too are one of them, for your accent betrays you.” [74] Then he began to invoke a curse on himself and to swear, “I do not know the man.” And immediately the rooster crowed. [75] And Peter remembered the saying of Jesus, “Before the rooster crows, you will deny me three times.” And he went out and wept bitterly.
PETER’S TEARS
That moment…hearing the rooster crow as the words leave your mouth…
The gospel of Luke even states that the Lord turned and looked at Peter (Lk 22:61) in that same moment.
Can you even imagine the grief…the sorrow…the devastation…Jesus’s words earlier that evening proved true. Peter did deny him three times.
Peter’s tears expose his undoing.
They expose how far off he was from who he thought himself to be.
They reveal his depravity.
They expose that he was not enough. Peter’s own skills, talents, abilities, resources…NONE OF IT. None of it was enough.
Not only do his tears show that he can’t even meet his own standard of courage, but they reveal he is not the man his Messiah called him to be.
His tears reveal his need for redemption and restoration.
His tears here in our text, beyond the entrance of this high priest's courtyard, reveal how far has moved from Jesus. Even physically he has left Christ’s presence. He did not stay with Jesus until death. He failed. He did not keep his word. He denied his Savior.
He was cowardly, not courageous.
His tears expose how far off Peter really was.
Our own tears expose how far off we really are too.
Our tears reveal that what we are experiencing is not what we should be experiencing. Our grief shows us that injustice and heartache are not the way it was supposed to be! When we fall short, we know it should not have been that way. We should have been better. If we are honest with ourselves, we all have these moments.
The distance between the way things are, and the way they should be hurts. We all so desperately want reality to be good, whole, unbroken. These desires touch on the deep longings of our hearts that we and this world should be whole.
Peter was the best of the disciples, the leader. In the inner circle with Jesus. He still failed.
No matter how hard we try. Or how bold we are. Or how desperately we work. Or how much money we make. Or how talented we are. Or how much time we spend. Or how good we get at something, we still experience the chasm between what is and what should be.
No matter how hard we try, we cannot traverse that distance.
But there is someone who can. There is someone who did. Jesus.
When we realize how far off we are, trust in the One who drew near to us.
Turn your gaze upon the One who can wipe them away. His name is Jesus. Draw near to him. As Peter runs away, Jesus presses forward. He crossed the chasm to make things whole again. He came to us, because we could not get to him.
We also know as we read through the remaining two chapters of Matthew that we will cover in the coming weeks that Jesus will traverse the chasm of death itself, and overcome it.
Jesus’ words of Peter’s denial proved true, but so did a few other things.
1) ‘I will strike the shepherd, and the sheep of the flock will be scattered.’
The sheep are gone. The shepherd now sits there…alone. [PAUSE] bound, a prophet rejected in his own home town. Beaten…bruises forming…only hinting at the horror that is coming.
2) ”But after I am raised up, I will go before you to Galilee.”
He will get back to his disciples in Galilee and to bring salvation to the whole world. He will bring life to what was dead. He will make things be as they ought to be.
The Shepherd takes the hit, in order to draw all the sheep into eternal safety. That is the Upside Down Kingdom.
CONCLUSION
I want to conclude with a few more items.
Matthew doesn’t give us much more to chew on when it comes to the story of Peter specifically. But if you go to the Gospel of John 21:15-19 you will see the story of Peter being restored and loved. I encourage you to go read that story in John 21 this week. Put yourself there with Peter and imagine Christ speaking to him and restoring him. Christ has that same love for you.
After Peter's restoration and Christ’s ascension, Peter goes on to do amazing things. He also messes up again too. The Book of Acts shares some of these things. At Pentecost, when the Holy Spirit arrives, Peter actually preaches a sermon where THREE THOUSAND people believe in Christ as the Messiah. Those are the types of things possible with the Holy Spirit when we focus on the things of God and not the things of man. Those of us who trust Christ as our savior have that same Holy Spirit with us!
Think about the context of Seattle. If the Holy Spirit at work through Peter transforms 3000 people, what could the Holy Spirit do through us in our own passion and zeal? We have such an amazing opportunity here!
What we often think of our city as the unchurched city. That is correct. But we kinda shift the blame a little bit. So connect some dots with me…who is responsible for Peter’s denial?
Is the crowd responsible? Maybe for being antagonistic? Maybe for making him afraid? Do we blame the scariness of the situation Peter is in that is happening in the middle of the night? NO!!! Peter is responsible.
Peter is not responsible for the crowd, or the high priest’s actions against Jesus, but he is completely responsible for how he acts within that context. So too are we responsible for how we engage with our city. Are we courageous? Are we bold?
Trust me. I get nervous every single time someone around here asks me what I do for a living. Or every time I am asked why I can’t bring my kid to a birthday party on a Sunday morning. I am like Peter. I need Jesus so desperately. But I am easily distracted. I need to work on this stuff too.
Focus on the things of God, not the things of man.
Look at Christ, not the waves and winds.
Stay close to Christ, even when the crowd starts closing in.
He is near. And he will never leave nor forsake us.
When we realize how far off we are, trust in the One who drew near to us.
We can’t change hearts. We can’t. That’s not our job.
But we can introduce people to the One who can change hearts.
We can trust the Holy Spirit to be at work. We can trust the One who closed the gap between what is and what ought to be.
When reality is so distant from the good, point it out! Draw people's attention to Christ who closed that distance. We can’t cross that distance. But he did in order to get to us. So introduce Him to those who don’t know him.
COMMUNITY GROUP QUESTIONS
When have you realized you’re not as courageous, faithful, strong, or “together” as you thought? Maybe you missed your own expectations or a biblical standard. What did that moment reveal about your need for Jesus?
What step can you take this week to point others to Jesus? Think boldly. Think of both Christians and Non-Christians.
Read John 21:15-19 together. You will see the story of Peter being restored and loved. Put yourself there with Peter and imagine Christ speaking to him and restoring him. Christ has that same love for you. What does Peter’s restoration mean for us in our day?Jesus
