Dissolving Disciples

Matthew 26:69-27:10

Immanuel – 6/29/25

          Matthew has been building to the events of death and resurrection since the very beginning of his Gospel. In chapter 3, Jesus said to John the Baptist, “It is fitting for us to fulfill all righteousness” (Matthew 3:15). He is now on the cusp of fulfilling all righteousness.

Everything that is happening – Jesus’ arrest, being condemned in court, and the cross soon to come – none of it is by accident. There is no room for chance in these unfolding events. The Father planned it all in eternity past; and in those ancient corridors of time, the Son of God joyfully agreed to walk the path of suffering (Hebrews 12:2). Jesus is not a victim – though he is victimized. Jesus is the prime actor.

And though Jesus is the prime actor, the story of his unfolding drama is interrupted to briefly consider two other actors in Matthew’s Gospel: Peter and Judas. Both are disciples of Jesus. Both have been with Jesus from the beginning. Both have seen his miracles and heard his teachings. Both have proclaimed the gospel of the kingdom of God. Both have a tremendous failure. But despite so many commonalities, their ends couldn’t be more different.

          I’ve broken this sermon up into two sections. First we are going to go through the stories of Peter and Judas and unpack what is going on in each account. Then we will take time to consider the similarities and differences of these two men, and what those things mean for us today.

          But before we get into it, let’s quickly review what’s been going on.

          Jesus has been brought before the Sanhedrin – the highest religious and political governing authority among the Jews. But this midnight meeting is filled with injustices, and the sole intent of the tribunal is to condemn Jesus to death. Ultimately, the whole council condemns Jesus to death for blasphemy, for equating himself with the divine Son of Man in Daniel 7.

          They then beat Jesus, and spit in his face, and mock him saying, “Prophesy to us, you Christ! Who is it that struck you?” They do not believe Jesus is the Christ and they do not believe he is a prophet: which is ironic, because just outside, one of his prophesies is being fulfilled.

          Let’s read that prophecy.

          Read vs 30-35

          The Fall of Two Disciples

          While Jesus stands before the injustice of the Sanhedrin and is mocked for being a false messiah and false prophet, Peter is experiencing the fulfillment of Jesus’ prophecy.

          Read vs 69-70     

          When Jesus was arrested in Gethsemane, Matthew recorded all the disciples left him and fled. But then in verse 58 we read that Peter followed at a distance to see the end. Peter is not in Caiaphas’ courtyard to mount a rescue mission, he is not there to die with Jesus; he is there with sad resignation, come to see the end.

But while waiting in the courtyard, a servant girl recognizes Peter. It is possible that the girl has seen Peter with Jesus earlier in the week. But the most likely people in Caiaphas’ courtyard at this dark hour are the same people who were in the crowd arresting Jesus. This girl probably recognized Peter from being in the Gethsemane with Jesus only hours before.

Notice how Peter’s association with Jesus is first questioned by a servant girl. A young girl, physically non-intimidating. A servant, socially disregarded. She is as non-threatening as they come, and she makes no accusation, just an observation: “You were with Jesus the Galilean.”

But even as non-threatening as she was, Peter claims to have no idea what she is talking about – a denial of the truth, a denial of Christ.

Read vs 71-72

Peter is now at the entrance to the courtyard and another, non-intimidating, servant girl makes the observation that Peter has been with Jesus. This time, the girl does not say it to Peter, but to the people sitting around. The first time Peter lied about Jesus, this time he perjures himself under a self-imposed oath, he says, “I do not know the man.”

I wonder if this is the exact moment when, inside, Caiaphas tries to put Jesus under oath. Jesus answers truthfully, but he will not take the oath. Jesus is fulfilling all rightesousness.

“I say to you, Do not take an oath at all… Let what you say be simply ‘Yes’ or ‘No’; anything more than this comes from evil.”                       -Matthew 5:34,37

Peter’s oath certainly comes from evil, for with it he denies the Messiah, the Son of God, for a second time. And for a period of time, perhaps an hour or so, things quiet down for Peter. But then, he is again confronted about his relationship to Jesus.

Read vs 73-74a

Peter was there to see the end. Perhaps he began asking questions about what was happening inside, trying to find out what was going on with Jesus. And the moment he opened his mouth, his accent betrayed him.

Galileans spoke a different dialect of Aramaic from the Jews of Judea, and the Judeans looked down on the Galilean accent. For instance, when you hear certain American accents, you know exactly where the speaker comes from. And certain American accents are stereotyped as sounding stupid. That is how the Galilean accent was for Judeans; meaning both Peter and Jesus sounded like uneducated outsiders to them.

Peter was a Galilean. Jesus was a Galilean. This group of people did not say they recognized Peter had been with Jesus; rather, since they both had the accent, they must be associated.

This time Peter flips out. His previous oath turns into swearing. He also curses. A number of commentators say the Greek words Matthew employ indicate Peter does not curse himself, but he curses Jesus instead. Either way, Peter evidently thinks an explosion of forceful and foul language will get the bystanders off his back.

On this dark night, when the supposed Messiah was inside doing nothing very messianic, and Peter’s 3.5-year hope was coming to a humiliating end, was Peter feeling ashamed of Jesus? Was this why he so vigorously denied Jesus this third time?

If he was feeling shame about Jesus, that shame was instantly turned on its head at the crow of a rooster.

Read vs 74b-75

As daylight nears, the rooster sounds, and Peter’s memory is immediately triggered. In his mind, he hears the words of Jesus, spoken only hours earlier: “Before the rooster crows, you will deny me three times.”

Peter emphatically said he would never deny Jesus. Now he has done it three times, and the taste of his filthy words are more bitter than he can handle. Peter runs from the palace of Caiaphas and weeps like never before – bawling his eyes out with overwhelming remorse.

Notice how with Peter’s three denials he moves further and further from Jesus, who is inside Caiaphas’ palace. First Peter is in the courtyard. Then he moves to the gate. Then, with the third denial, he runs away entirely. Every denial heightens the separation. Every denial pushes Peter further into the dark.

In Matthew’s Gospel, this is the last time Peter is mentioned. The leader of the twelve falls spectacularly.

Read 27:1-2

Dawn has come, and it also seems all 71 members of the Sanhedrin had finally arrived at Caiaphas’ palace. Jesus is probably in some holding cell. They review the evidence, and the divine claim Jesus had made of himself, and together they reach an official verdict: Jesus must die. The retrieve Jesus, bind him once again, and send him off to Pontius Pilate.

Pilate was the Roman prefect, or governor, of Judea. Only he could sentence Jesus to death and carry out the execution. This is not good news for Jesus, because Pilate had a reputation for being a hard man; having treated the Jews with cruelty numerous times in the past.

Nonetheless, Jesus’ prophesies were coming true with precision.

As Jesus was going up to Jerusalem, he took the twelve disciples aside, and on the way he said to them, “See, we are going up to Jerusalem. And the Son of Man will be delivered over to the chief priests and scribes, and they will condemn him to death and deliver him over to the Gentiles to be mocked and flogged and crucified, and he will be raised on the third day.”                                 -Matthew 20:17-19

Jesus’ prophesies were fulfilled with precision. And the events he foretold were touched off by one of the 12 who heard Jesus make this prophesy.

Read vs 3-4a

Somehow, when Judas understood Jesus was condemned to die, the overwhelming gravity of his choices came over him – like it did for Peter when the rooster crowed. Judas is seized with remorse (as the NIV says) and changes his mind, when he tastes the fruit of his betrayal.

Judas turns to the chief priests, the same ones that paid him, and he admits his sin. Judas truly confesses his sin; he has betrayed innocent blood. There is only one man that has even been truly innocent, perfectly sinless, and that is the man Judas has betrayed unto death. The guilt that grips him is like claustrophobia and he would do anything to escape its squeeze.

And seeking any way out, in desperation for some relief, Judas attempts to return the 30 pieces of silver. But the religious leaders are not too interested in helping Judas. He is a tool they have used and now that he has served his purpose, they are ready to discard him.

Read vs 4b-5

Perhaps by giving them Jesus, Judas thought he had earned the favor of the chief priests – in addition to the silver. He didn’t. They didn’t have even a shred of respect for him. “Oh, you feel bad? Who cares. Get away from us and get over it.

This is exactly what Jesus condemned the religious leaders for.

“They tie up heavy burdens, hard to bear, and lay them on people’s shoulders, but they themselves are not willing to move them with their finger.”     -Matthew 23:4

These religious leaders cared nothing for Judas’ desperate spiritual need. They used him and were done with him. This is disgusting spiritual abuse, and it disgusted Jesus. Sadly, so many personality driven churches are marked by spiritual abuse like this, where leaders use the people for their own purposes and care little for the spiritual needs of their flock.

Judas’ guilt is so extreme, his leaders so abusive, his separation from Christ so vast, that the only escape he sees is through death. He commits suicide. Horrifically, in death, he finds no escape. Jesus called Judas the “son of destruction” (John 17:12), for destruction he reaped and to destruction he goes.

Read vs 6-8

How ugly of the chief priests: so willing to shed innocent blood, so sanctimoniously unwilling to use blood money – money they authorized to go out was money they would not receive back. Certainly they imply that the reason the money became impure, and not worthy of their temple, was Judas.

The use the unclean money for an unclean purpose, and purchase a field to make a graveyard – likely a graveyard for Jewish pilgrims who die far from home.

Judas’ betrayal and inglorious end became locally memorialized, when the field was give the name, “blood.”

Read vs 9-10

Matthew loosely quotes Zechariah 11:13. It’s less of a quotation and more of a mosaic, with parts woven together from different passages, though Zechariah is primary. Ultimately, Matthew quotes this mosaic to emphasize Jesus was the shepherd rejected by his sheep, hated and devalued by the “sons of Israel.”

But all of it accorded with the plans of God. The people were responsible for their own actions, but God was sovereignly guiding every event – to redeem a people and bathe existence in a flood of his awesome glory!

The account of Judas’ death is another instance where Matthew has not arranged things chronologically, but thematically. When Judas throws the money at the chief priests, it hits the temple floor. In verse 2 the chief priests are in Caiaphas’ palace. They then go with Jesus to make their case before Pilate. It is highly unlikely they will be hanging out in the temple in between.

The scene where Judas throws the silver coins back at the chief priests likely occurred after Pilate condemned Jesus, perhaps even while Jesus hung on the cross. So why did Matthew put Judas’ suicide before those things? I think it’s because he wants us to see Peter and Judas side-by-side, how they are similar, and how very different they are.

Lessons on Repentance

Let me again highlight something that is true for both Peter and Judas: both feel remorse, overwhelming remorse. Though we only hear Judas say he has sinned, Peter’s bitter weeping means he knew he also had sinned.

These things they share, but there is one massive difference between the two men. In his grief, Judas seeks death. In his grief, Peter seeks a restored life. I said that Peter is not mentioned again in Matthew’s gospel, but we read this just before the close of the book.

Now the eleven disciples went to Galilee, to the mountain to which Jesus had directed them.                                                           -Matthew 28:16

Eleven means Peter is again with the disciples! He has gone with them to meet the resurrected Christ. And from the other gospels, we know that Peter joined up with the disciples less than 48 hours after his denial. Following his bitter weeping, he went looking for James and John, Andrew, Simon, and all the rest. He wanted to be with his friends. He wanted to be near those who had been near to Christ.

But think carefully about this, if both men were deeply grieved by what they had done, what separated the two of them? Why was one accepted and the other rejected? Why did one receive life and the other death?

There is a New Testament passage I find so helpful here. It powerfully clarifies the difference between Peter and Judas and the grief they each felt.

For godly grief produces a repentance that leads to salvation without regret, whereas worldly grief produces death. For see what earnestness this godly grief has produced in you, but also what eagerness to clear yourselves, what indignation, what fear, what longing, what zeal, what punishment! At every point you have proved yourselves innocent in the matter.                                             -2 Corinthians 7:10-11

Paul teaches that there are two types of grief. One leads to death, the other to salvation. Are not Peter and Judas profound examples of this? The grief that leads to death is guilt/regret without resolution. Salvation is found in godly grief, because godly grief leads to repentance; and in repentance we find freedom from guilt.

Let’s again look at the two men to understand this distinction better. First Judas, and his guilt/grief/regret without resolution that leads to death.

          When Judas finally realized what he had done, he did not take his grief to God. He took it to the religious leaders. He thought they would be able to comfort him, or somehow absolve him of his sin; but instead they disrespected him. They heaped grief upon his already overflowing grief. Judas sought forgiveness in men rather than in God.

          Why did Judas want to give the 30 silver coins back? Obviously, he wanted to undo what he had done. If he could have reversed time, he would have. If he could have covered up his sins, he would have. Even in his regret, Judas did not want to be desperate and needy, he did not want to come to God naked and afraid; he wanted to fix the problem himself. He thought he could solve it. He was trying to build his own path of salvation. He even went so far to find salvation in a noose. That’s the sick delusion of self-made salvation: It is our death.

          Judas proved in his life and his death, that he was self-oriented. His grief was an expression of selfishness; or as Paul wrote it was worldly grief.

Now let’s shift our focus to Peter and his grief that produces repentance, a repentance that leads to salvation. All four gospels tell of Peter’s denial. None of them were there. The only way they could have known is if Peter confessed his failure to the disciples.

And he could only do this because Peter sought to be with his friends. He wanted to be near those who were near to Jesus. They were the closest he could find to the presence of Christ. Peter sought repentance in community. And in the days to come, after the resurrection, Jesus himself gave Peter a three-fold restoration for his three-fold denial (John 21:15-19). Afterwards Peter traveled the Roman empire proclaiming the name of Jesus. He would die like Christ, unjustly crucified – though he felt unworthy to be crucified like his Savior, so he chose to be crucified upside down.

Peter proved in his life and his death that he was Christ-oriented. His grief was an expression of pain for sin. Paul called this godly repentance.

Peter’s tears were only the beginning of repentance. More necessarily had to follow. Remember again what Paul wrote.

For godly grief produces a repentance that leads to salvation without regret, whereas worldly grief produces death. For see what earnestness this godly grief has produced in you, but also what eagerness to clear yourselves, what indignation, what fear, what longing, what zeal, what punishment! At every point you have proved yourselves innocent in the matter.                                             -2 Corinthians 7:10-11

If grief is to be godly, if repentance is to be earnest, then Paul says the following things will occur in a person; as they did in Peter.

An eagerness to clear yourself: You want to confess. You long to get it off your chest.

Indignation: There is an anger with sin, because you know it leads to destruction – destruction in yourself and destruction in others. You’re so fed up with the destructive power of sin that you will no longer tolerate it.

Fear: This is surely the fear of the Lord. How terrible to be found sinful before a holy God, for our God is a consuming fire! In repentance you seek his mercy, that he would turn his away wrath for your sin. This is the exact reason Christ when to the cross, to take God’s wrath for your sin, so you would not have to. To fear God is to trust in Christ’s complete work of forgiveness for sins.

Longing: You yearn to be restored and reconciled. Your heart burns for it.

Zeal: You passionately take action to reconcile yourself to others. You restore all that has been ruined – like Zaccheus restored fourfold all he had defrauded.

Punishment: If there are any consequences for your sins, you are willing to accept them. You do not weasel out of them or hide yourself from them. You place yourself in the fire and trust that God will refine you through the process.

Peter’s grief was godly. His repentance, earnest. Brothers and sisters, what has repentance been for you? Have you found freedom from guilt in the forgiveness of Christ? Have you born the fruit of repentance, and gone on to orient your life around Christ? Or, like Judas, do you know regret that is focused on self, a guilt that has no resolution?

Let me share with you a few more words from Jesus.

“Everyone who acknowledges me before men, I also will acknowledge before my Father who is in heaven, but whoever denies me before men, I also will deny before my Father who is in heaven.”                                                -Matthew 10:32-33

          Peter, the rock whom Jesus said he would build the church upon, denied Jesus before men. But even here, Jesus is gentle and lowly, abounding in steadfast love and mercy, eager to forgive. If we come to him with a repentant heart, he will forgive even our denials. He will forgive the very worst of our sins.

Read 1 Peter 5:10-11

          True repentance means a new way of life, a turning away from what was before, and turning to a life dedicated to following Jesus, even if there is a cross at the end. It’s why Peter wrote, in the passage we just read, “To him be the dominion forever and ever. Amen.”