Peter & Judas - Matthew 26:20-35


A.  Regret

1.   Have you ever experienced regret?

a.   I don’t mean regret for missing a sale at Mervyn’s or Kohl’s, or for shooting the ball when you should have passed.

b.   I mean the bitter regret that reduces even a big, tough man to a bawling crybaby.

2.   We’ve all known the mild regret of some unfortunate decision,

a.   of saying something silly, or not speaking up when we should have.

b.   many of us have known the regret that comes from not watching the speed limit,

c.   or looking twice when we backed up the car.

d.   but that’s not the regret I’m referring to.

3.   I’m talking about the regret that is a grief so great it takes over your emotions;

a.   an emotional pain so intense, all you can do is double over, clutch your sides & moan because you feel like you’re coming apart inside.

b.   you’ve made a choice that has set in course a series of events that have caused your world to end – or so it seems.

c.   and the regret is so intense you’re overwhelmed with grief & sadness.

B.  What Brought Them Here?

1.   We’re taking a look today at two men who experienced this kind of regret & how each of them handled it.  These two men are Judas & Peter.

2.   When I prepare a message for the weekend services, I usually have the entire fellowship in mind and intend the message for all.

3.   I sense that this message is different; that the Lord intends it for a specific group of people, maybe even just one person – someone who’s in great danger.

a.   there is someone listening whose life is in danger.

b.   he/she has come to a place of the deepest regret and has entertained thoughts of suicide.

4.   I hope and pray this message will be used by the Lord to pull you back from that dark place and be the turning point of a new life for you.


A.  Vs. 20-25

1.   Matthew tells us about the Last Supper -

20When evening had come, [Jesus] sat down with the twelve. 21Now as they were eating, He said, “Assuredly, I say to you, one of YOU will betray Me.” 22And they were exceedingly sorrowful, and each of them began to say to Him, “Lord, is it I?” 23He answered and said, “He who dipped his hand with Me in the dish will betray Me.

2.   They were all eating out of the common bowl – something friends did.

3.   Jesus was telling them that one of them, one of those who appeared to be a friend would in fact do the most unfriendly thing.

4.   Then Jesus said . . .

24The Son of Man indeed goes just as it is written of Him, but woe to that man by whom the Son of Man is betrayed! It would have been good for that man if he had not been born.”

5.   The death of Christ was the reason He’d come and it would be accomplished no matter what.

a.   but that did not relieve those responsible for His death of their culpability.

b.   not one of them was forced to do what they did, God did not ordain them as individuals to arrest, condemn, and execute Jesus.

c.   each actor in that great drama willingly took part.

6.   Judas was the one who’d volunteered to play the role of betrayer.  In vs. 14-16 we read –

14Then one of the twelve, called Judas Iscariot, went to the chief priests 15and said, “What are you willing to give me if I deliver Him to you?” And they counted out to him thirty pieces of silver. 16So from that time he sought opportunity to betray Him.

a.   Judas had cut a deal with the rulers to betray Jesus at the earliest opportunity.  The price of his loyalty was 30 pieces of silver.

b.   all the plans & ambitions that had moved him to follow Jesus 3 years before had proven hollow,

c.   so he decided to bail while he could still make a profit out of his relationship with Jesus.

7.   Jesus knew all about Judas’ arrangement with the priests & how even at that moment as they sat at supper, the religious police were gathering at the temple to meet up with Judas, who would then lead them to arrest Jesus.

8.   Jesus is never taken by surprise – & He wanted to let the disciples know that when He was betrayed in just a few hours from then, He knew all about it.

9.   But there was another even more important reason Jesus forewarned them of His betrayal –

a.   He wanted Judas to turn from the course he’d chosen.

b.   it wasn’t too late.  Even now, though the silver coins were jingling in his pocket, it wasn’t too late to turn from the path of betrayal, to repent and be restored.

c.   would Judas take the gift Jesus was handing to him?

10. John’s gospel tells us Jesus took a piece of bread at this point, dipped it into the bowl to scrap up some of the lamb that was the Passover meal, and handed it directly to Judas!

a.   it was an invitation to fellowship, to forgiveness and renewal.

b.   and we can be sure as the bread passed from Jesus’ fingers to Judas’, their eyes met and held.

 25Then Judas, who was betraying Him, answered and said, “Rabbi, is it I?” He said to him, “You have said it.”

11. Judas’ question proved where his heart was–totally out of touch with the Lord & not at all interested in renewal.

12. His question was a mask for his sin.  If he’d had a true & tender heart, Jesus words would have cut to the quick & brought him to his knees then & there.

13. But his mind is distracted as he thinks about pulling off the plot; already planning how he’ll use the money.

14. When Jesus tells him that he is indeed the betrayer; it’s his final  opportunity to repent.  Judas sees it as a release to go and carry out his plot.

15. It’s at this point he leaves to go meet with the temple police.

B.  Vs. 31-35

1.   Now we turn to Peter -

31Then Jesus said to them, “All of you will be made to stumble because of Me this night, for it is written: ‘I will strike the Shepherd, And the sheep of the flock will be scattered.’ 32But after I have been raised, I will go before you to Galilee.”

2.   Again, Jesus knew what was coming; He knew that before the night was over the disciples would all abandon Him.

3.   When they did, He didn’t want them to think He held it against them –

4.   On the contrary, when He rose from the dead, there would be a great reunion back in their old stomping grounds in Galilee.

5.   But Peter was offended by the thought that he’d forsake the Lord and spoke up -

33Peter answered and said to Him, “Even if all are made to stumble because of You, I will never be made to stumble.”

6.   Remember that Jesus had renamed him from Simon to Peter, the Rock!

7.   And here Rocky speaks up and says that while the rest of the wimpy disciples might bail, not he!  No siree!  He’s a rock of devotion!

8.   Peter had great confidence in himself; he knew he was no coward and that he was utterly loyal to Jesus.

34Jesus said to him, “Assuredly, I say to you that this night, before the rooster crows, you will deny Me three times.” 35Peter said to Him, “Even if I have to die with You, I will not deny You!” And so said all the disciples.

9.   It is never wise to argue with Jesus!  If He says a thing will be, it’s best to accept it.

10. But Peter was adamant & protested his devotion to Jesus would not falter.

11. His assertions moved the other disciples to the same vow.

12. Of course, we know that Jesus was right and Peter was wrong here.

13. Friends - Beware the bold assertions of self-confidence!

a.   Peter had the very best of intentions – he really did not think that He would forsake the Lord, let alone deny Him.

b.   as he looked into himself, he saw determination & resolve.

c.   what he didn’t see was what was to come.  He had no idea how fierce the trial he was about to endure was, or how confusing the turn of events.

C.  Vs. 69-75

1.   Now let’s look to the end of the matter for Peter.

a.   Jesus has been arrested & hauled before a sham trial at the house of the high priest.

b.   while the trial by the leaders is underway inside, the temple police & mob that had come to watch is outside in the courtyard trying to stay warm by a fire they’d built.

c.   Peter had tagged along at a safe distance until he got into the courtyard & found a spot among the others by the fire.

69Now Peter sat outside in the courtyard. And a servant girl came to him, saying, “You also were with Jesus of Galilee.” 70But he denied it before them all, saying, “I do not know what you are saying.” 71And when he had gone out to the gateway, another girl saw him and said to those who were there, “This fellow also was with Jesus of Nazareth.” 72But again he denied with an oath, “I do not know the Man!” 73And a little later those who stood by came up and said to Peter, “Surely you also are one of them, for your speech betrays you.”

2.   Peter spoke with the accent of a Galilean; a dead give-away.

74Then he began to curse and swear, saying, “I do not know the Man!” Immediately a rooster crowed.

3.   Peter’s denial of being one of Jesus’ men wasn’t just a casual brush off.

a.   it was a volatile & vehement tirade!

b.   he swore, took an oath, & turned angry insults at those who’d called him down.

c.   his hostility only added to the certainty of those who looked on that he was indeed a disciple!

4.   The words of Peter’s third denial of Christ were barely out of his mouth when a rooster crowed, signaling the coming dawn.

75And Peter remembered the word of Jesus who had said to him, “Before the rooster crows, you will deny Me three times.” So he went out and wept bitterly.

5.   Jesus had called it – and just as He said, so it was!

6.   When the rooster sounded, Peter remembered what Jesus had said, and his own protestations of fidelity were shown to be the empty things they were.

7.   Luke tells us in his gospel that at the third denial, when the rooster sounded, Jesus and Peter’s eyes met.  [Luke 22:61]

8.   At this Peter fled the courtyard and found a solitary place to pour out his regret.

9.   Matthew describes Peter’s grief in the strongest possible way. “He wept bitterly.”

a.   these are the same words used to describe the weeping of a husband or wife over their dead spouse.

b.   or of a mother or father who stands over their dead child.

c.   this is the kind of grief that causes a person to double over and clutch their sides because they feel like they’re coming apart inside.

d.   it’s a sobbing so great, that at first there are tears, but then you come to a point where the tears stop because the sense of sorrow is so profound tears are too petty an expression of the emotional torment you feel.

10. At this moment, Peter’s whole world lay in ruins.

a.   Jesus was in the custody of men who had vowed to kill Him.

b.   and Peter’s last chance to prove his loyalty to Christ had been squandered, or so he thought.

c.   all his hope & expectations in Jesus had been dashed,

d.   and everything he’d hoped & believed about himself had proven untrue when put to the test.

11. In the garden of Gethsemane when the armed mob had come to arrest Jesus, Peter had grabbed a sword and started swinging.

a.   his bravado & courage had shined forth then,

b.   but now in the courtyard of the high priest, at the charge of a couple young servant girls, he crumbles into a cowardly traitor.

12. There is one word that characterizes Peter at this moment – REGRET!

D.  Vs. 27:3-5

1.   Now let’s return to Judas and see how he fared . . .

3Then Judas, His betrayer, seeing that [Jesus] had been condemned, was remorseful [regretful] and brought back the thirty pieces of silver to the chief priests and elders, 4saying, “I have sinned by betraying innocent blood.” And they said, “What is that to us? You see to it!5Then he threw down the pieces of silver in the temple and departed, and went and hanged himself.

2.   Judas, like Peter, was filled with regret at what he’d done.

3.   When he knew his role led to the condemnation & would result in the execution of a good man, he realized his terrible error – and sought to undo it.

4.   When he couldn’t, his regret went past the place Peter’s had gone, all the way into despair.

5.   To Judas’ way of thinking, there was only one way to escape the pressing sense of guilt his soul was under – to end it by taking his life.

E.  Dealing With Regret

1.   Peter & Judas present us with two very different ways of dealing with regret over having failed in our walk with the Lord.

2.   Both men were stricken with the deepest regret.  Both knew crushing grief over how they’d failed.

3.   The difference between them is this à

a.   while Judas felt his sin was too great to be forgiven,

b.   Peter held on to the hope that God’s forgiveness was bigger than his sin.

4.   Judas had learned nothing about the mercy of God in the time he’d spent with Jesus.

5.   Peter had taken the lessons Jesus taught on forgiveness to heart, and held out hope that he would find forgiveness.

6.   When Jesus rose from the dead three days later, an angel met the women who’d come to the tomb to prepare His body for permanent burial.

a.   he sent them back to the disciples with word of Jesus’ resurrection. 

b.   in Mark 16:7 we read. . .

“But go, tell His disciples—and Peter—that He is going before you into Galilee; there you will see Him, as He said to you.”

c.   we can be so thankful for this verse, and for the way the angel singled Peter out here.

7.   You see, after his denial of Christ, Peter didn’t feel like much of a disciple!

a.   when these women returned to find the disciples huddled & hiding in their room, they would report what the angel had told them.

b.   they would say, “He said were should come to you, the disciples, and tell you Jesus is risen.”

c.   and Peter would say to himself, “Well, I’m no longer a disciple! My actions, my denial of Jesus has surely resulted in my rejection from belonging to Him.  Certainly He doesn’t want me anymore!”

d.   God knew Peter was thinking this way, and directed the angel to mention Peter specifically!

“But go, tell His disciples—and Peter!”

8.   At this word, Peter’s hope was further kindled.

9.   It was fully restored when the Lord Himself appeared to Peter and let him know he was forgiven.

a.   in three successive challenges, Jesus gave Peter a path back to full fellowship with Him,

b.   and restored Peter to a place of effective ministry among the apostles.

10. The mercy and grace Jesus showed Peter broke him of his self-confidence & of all that which had led to his downfall.


A.  Judas Or Peter

1.   Chances are, a good number of us in this room are going to fail, & fail miserably in our walk with the Lord at some point.

2.   The flesh, greed, lust, self-confidence, prayerlessness, all the things that contributed to Judas’ & Peter’s demise will lead to ours.

3.   Odds are, some here now are in the place Judas & Peter were in our study today – filled with deep regret at making a choice or set of choices that have led to what seems like the end with little to no hope of a turn around.

4.   Do not follow the path of Judas – remember Peter!

5.   Our God is a merciful God who delights in taking what seems like an impossible situation and turning it around to bring forgiveness and restoration.

6.   He is a God of New Beginnings!  He is the God of the Resurrection, of bringing life out of death.

7.   There IS no reason to hope in yourself, but there is always plenty room & reason to hope in God.

8.   You may be a total failure – God cannot fail!

9.   As long as we draw breath, there is reason to hope in the goodness and power of God.

B.  The Battle

1.   Know this – when you find yourself in the pit of despair – when you are filled with regret, it’s because you’ve followed a path laid by the enemy of your soul who from the start had a single goal in mind – to destroy you!  Jesus said the devil comes to steal, kill, and destroy.

2.   The grief you sense is the pain he’s inflicted.

3.   That grief will turn in one of two directions –

a.   if you listen to the Spirit of God, then it will turn to conviction of sin that leads to repentance, and repentance will lead to forgiveness, and forgiveness to the restoration of life and the joy of your salvation.

b.   but if you listen to the enemy, then grief will turn to condemnation, and condemnation to despair, and despair to self-destruction.

4.   Conviction is from God and draws us to Him.  Condemnation is of the devil and drives us away from the Lord.

5.   Which voice are you listening to, the voice of conviction calling you to forgiveness, or the voice of condemnation that’s calling you to despair?