The Repentant Robber – Luke 23:39-43


A. The Monkey Trap

1.  Though not so popular anymore, several decades ago, pet monkeys were much sought after.

2.  Trappers made a tidy sum by selling wild monkeys to merchants who would train then sell them to the wealthy & to circuses who used them to entertain the crowds.

3.  The way they trapped wild monkeys was ingenious.  They used what was called, fittingly enough, a Monkey Trap.

a.  It was a coconut or small wooden box with a chain attached to one side of it.

b.  The trapper would attach 1 end of the chain to a tree near where monkeys sat watching intently.

c.  He’d then take a bright, shiny bauble out of his pocket & show it to the curious monkeys.

d.  Once they’d all had a chance to see the sparkly thing, he’d drop it through a small hole in the side of the trap.

e.  Then he’d walk away, and go to another place in the jungle and repeat this same process with another group of monkeys.

f.   Once he’s set all his traps, he’s go back & collect his prize of monkeys, putting them in the cages stacked on his cart.

g.  You see, as soon as he set a trap & left, some curious monkey would rush to the coconut, stick his little hand into the hole and feel around for the bauble.

h.  Grasping it, the monkey would then try to draw back it’s hand, which being in the shape of a fist was now too large to slip through the hole.

i.   The chain made sure the little guy didn’t drag the trap off to some hiding place.

j.   All the trapper had to do was come along later and collect his monkeys who refused to let go of their shiny but worthless prize.

B. Clever Monkeys

1.  The monkey trap is a great illustration of the snares the devil sets for people through lust & greed.

2.  But what isn’t usually mentioned in the illustration of the monkey trap is that not all monkeys were snared this way.

3.  While most would put their hand into the hole & so where caught,

4.  There were a few who figured out how to get lose.

5.  After realizing they couldn’t withdraw their hands while clutching the bauble, they’d let go, pick up the trap, turn it upside down, & take the prize when it dropped to the ground.

6.  When the trapper returned, he’d find the trap empty & the monkey sitting on some nearby limb or rock, playing with his new toy. The monkey had outwitted the man.

7.  But the trapper wasn’t too concerned, he had a whole cart load full of less clever monkeys, & plenty more baubles for many more days of trapping.

8.  As I said, the monkey trap is a great illustration of the way Satan uses lust & greed to seduce & snare people.

9.  But it’s the clever one that escapes the trap we want to look at today.

10.     And we see it illustrated in this story of the repentant thief.


A. Set The Scene

1.  Our setting is the crucifixion.

a.  It’s some time before noon; how long Jesus has been on the cross we don’t know, but it could be a couple hours.

b.  It will be over 3 hours before the end of the ordeal.

2.  The Gospels tells us Jesus wasn’t the only one executed that day.

a.  While the Romans tried to pacify the often rowdy Passover crowds by releasing a political prisoner at this time each year,

b.  They also wanted to remind them that defying Rome was deadly.

c.  The reminder came by way of a small number of executions.

d.  This year, there were to be 3 – 2 robbers & an insurrectionist named Barabbas.

e.  The Roman governor Pilate had hoped to release Jesus as the token of Rome’s mercy –

f.   But the Jewish leaders had stirred up the crowd to demand Barabbas instead.

g.  So Jesus was given the cross that had been meant for Barabbas.

3.  As we saw in our study Wednesday, the name Barabbas means “Son of the father.”

a.  In taking Barabbas’ place on the cross, Barabbas becomes a type for you & I.

b.  For not only did Jesus take Barabbas’ place, He took ours!

c.  Jesus died on the cross to atone for our crime, to pay for our sin.

d.  Through His act of redemption, we can become the Sons & Daughters of a Heavenly Father.

e.  As it says in John 1:12 -

As many as received Him, to them He gave the right to become children of God, to those who believe in His name.

4.  All 4 of the gospels tell us Jesus’ cross was set between the other 2.

5.  On them were placed 2 men Luke calls “criminals” here in the NKJ.

a.  In the older KJ they’re called “malefactors.”

b.  The Greek word means an evil-doer,

1) But not someone who occasionally messes up,

2) This refers to someone whose habit is to commit crime, so the NKJ translation is a good one.

c.  We’d refer to these guys as “career criminals.”

d.  They weren’t everyday citizens who held down normal jobs & had been picked up for too many unpaid parking tickets.

e.  They were hardened crooks who made their living by committing crime.

f.   In the NKJ, Matthew & Mark call them “robbers” / the older KJ calls them “thieves.”

1) But a thief is someone who steals with stealth.

a) The thief avoids being seen; breaking in when the owner is away or asleep.

b) the whole goal is to get away unseen.

2) The word here refers to one who could care less about being seen.

a) He steals openly, brazenly.

b) He’s the mugger, the robber, the guy who comes up to you in the parking lot or alley, sticks a gun in your face and demands your money.

3) This is Jesse James, the Dalton Brothers, John Dillinger.

g.  There’s a term for this kind of criminal they use in Russia that I really like – Hooligan!

1) A hooligan is a bad apple, a career criminal everyone knows is given to a life of crime.

2) They have laws against hooliganism in Russia & the prisons are packed with men who’ve been convicted of being a hooligan.

h.  These 2 guys were hooligans; brigands, highwaymen who waylaid travelers.

i.   These were the kind of guys responsible for beating up the man in the Story of the Good Samaritan.

j.   They’d caused much trouble until the Romans had sent troops to track them down and apprehend them.

k.  There were many victims of their crimes who’d given testimony against them at their trial.

l.   The penalty was death – so here they were, being made an example of what happens if you defy Roman law.

6.  In Matthew 27, we read that when the 3 were first placed on their crosses, both robbers reviled Jesus.

38 Then two robbers were crucified with Him, one on the right and another on the left. 39 And those who passed by blasphemed Him, wagging their heads 40 and saying, “You who destroy the temple and build it in three days, save Yourself! If You are the Son of God, come down from the cross.” 41 Likewise the chief priests also, mocking with the scribes and elders, said, 42 “He saved others; Himself He cannot save. If He is the King of Israel, let Him now come down from the cross, and we will believe Him. 43 He trusted in God; let Him deliver Him now if He will have Him; for He said, ‘I am the Son of God.’ ” 44 Even the robbers who were crucified with Him reviled Him with the same thing.

a.  The Jewish rulers couldn’t help but come to gloat over Jesus as he hung on the cross.

b.  They circled like a pack of vultures, tossing out their taunts and insults.

c.  Jesus had done & said some amazing things during the previous 3 years, so they waited now to see what would happen.

d.  They tried to goad Him into saying something that would be the icing on the cake of their victory.

e.  As the insults flew, the robbers joined in, following the herd mentality that often marks a crowd.

7.  Of the time Jesus spent on the cross, the worst, the most agonizing, was when the Father turned away His face & Jesus cried out, “My God, why have You forsaken Me!”

a.  But the most trying had to be when the rulers mocked Him.

b.  Jesus was dying, not for Himself, but for THEM – for the very people who were treating Him with such hideous dishonor.

c.  Not only did they not deserve what He was doing, their mocking sneers must have tempted Him to revenge!

d.  All He had to do was say, “That’s enough,” and He could have stepped away from the cross and made them writhe on the ground in the utmost pain.”

e.  How great the mercy of Christ, how strong His long-suffering that He stayed on that cross in the face of such unjust scorn.

8.  As the hours stretched on & the day grew warmer, the rulers got tired of waiting & disappointed in the meek way Jesus was dying.

9.  So they returned to the city; leaving the Roman execution detail, the Passover crowds who passed by, & a handful of Jesus’ followers who stood at a distance.

B. V. 39

1.  As the agony of the crucifixion grew, one of the criminals became desperate.

2.  He knew where all of this would end if something wasn’t done quickly.

3.  So renewing his earlier taunts, we read in v. 39 . . .

39 Then one of the criminals who were hanged blasphemed Him, saying, “If You are the Christ, save Yourself and us.”

4.  To blaspheme means to speak evil of God.

5.  This man’s blasphemy was that while he didn’t at all believe Jesus was the Messiah, he tried to provoke Him to action by more mocking.

6.  Remember who the 3 crosses were originally intended for – Barabbas & these 2 brigands.

a.  Luke tells us in v. 19 that Barabbas had led an insurrection.

b.  He was one of several during this period of history who refused to submit to the Romans.

c.  Taking refuge in the countryside, & gathering malcontents around them,

d.  They would attack a Roman outpost here or there, & provided for themselves by robbing unwary travelers.

e.  There’s a very good chance the 2 robbers crucified with Jesus were part of Barabbas’ band of rebels who’d been caught with him.

7.  While their leader had managed to avoid his appointment with a cross that day, they were suffering for following him.

a.  This guy saw Jesus in the same way he’d viewed Barabbas; as just another faker who presented himself to Israel as her Savior, the long hoped for Messiah.

b.  And just as Barabbas had his band of loyal followers, Jesus had the disciples.

c.  Surely, at a word from Jesus, those followers would now step forward & come to His aid.

d.  They’d overpower the few Romans of the execution detail & rescue their Master.

e.  This guy was trying to provoke Jesus into saying the code-word that would save, not only Him, but them as well.

8.  But his appeal wasn’t the simple request of a believer in Jesus; it was more of the mocking he’d delivered earlier –scorn meant antagonize Jesus & provoke Him to action through anger.

C. V. 40-43

1.  But this time, the other criminal refused to join his companion.

40 But the other, answering, rebuked him, saying, “Do you not even fear God, seeing you are under the same condemnation? 41 And we indeed justly, for we receive the due reward of our deeds; but this Man has done nothing wrong.”

2.  Something had happened to the robber during the couple hours since they’d first been put on the cross.

3.  He’d listened to what Jesus said & watched the humble way He bore the ordeal.

a.  He considered his own behavior & speech –

1) How he reviled the guards & hurled insults at the crowd.

2) He thought of his own shameful remarks toward Jesus, though He’d done nothing to deserve them.

b.  What had Jesus said?  “Father, forgive them, for they don’t now what they’re doing.”

c.  When Jesus’ mother approached His cross, He’d spent some of His hard-purchased breath to ask one of His followers to take care of her.

d.  Not a word was given in reply to the mocking of His enemies.

e.  And instead of angry stares, Jesus gave back to the gestures of His tormentors nothing but the look of heartbroken mercy.

4.  This criminal had taken thought to all this, & realized that Jesus was different – he wasn’t like other men.

5.  The Roman centurion who presided over the execution would come to the same conclusion in just a few more hours when Jesus finally died.

6.  This robber arrived their first. And at the mocking of his companion, he speaks up, though speech is difficult as he hangs on the cross.

7.  Though this guy began by mocking Jesus, his opinion has changed.

a.  He admits that he and the other guy deserve their judgment.

b.  Their crimes had earned a cross.

c.  But now that he’d had a chance to watch Jesus for a few hours, he could see that the things He’d heard about Him were true.

d.  He wasn’t just a good man who’d upset the Jewish authorities.

e.  He was who He & His followers claimed He was – the Messiah; the Son of God.

8.  And He was hanging on a cross that had been meant for another.

9.  Though He was there unjustly, He was there willingly.

10.     This thief was the first person to realize that the cross was somehow a part of God’s plan & that the Messiah would gain His Kingdom by it.

11.     Look at what He said -

42 Then he said to Jesus, “Lord, remember me when You come into Your kingdom.”

12.     He called Jesus, “Lord,” & declared his faith in Him as the Savior.

13.     Based on that faith, Jesus could reply -

43 And Jesus said to him, “Assuredly,

14.     For sure!

I say to you,

15.     The one who’s just expressed faith in Him as Savior.

today you will be with Me in Paradise.”

16.     We won’t go into the details of what & where Jesus meant by this, this morning.

17.     Ultimately, what Jesus promised him was eternal life in heaven.


A. Focus

1.  What I want to focus on this morning is the change this man went through.

2.  For us, his story begins as a career criminal.

a.  But like all men, his life more than likely began as a little boy, the son of a loving mother.

b.  His father had had high hopes for him; maybe he would grow up to take over the family business, & another generation of millers, or masons, or merchants would be added to a rich family legacy.

c.  As he grew up, he played with the neighbor kids under the watchful eye of caring parents.

d.  But his father died when he was 14, & there was no one else to provide for his mother and he, so he’d tried to carry on the family business all on his own.

e.  He was too young to do the work, & the business declined.

f.   Blaming the Romans for the high taxes & the harsh conditions in his village, he held them responsible for the early death of his father & his inability to provide for his mother.

h.  When he heard of a Jewish freedom fighter living in the hills not to far from his village, he went off to join up.

i.   The rebel leader’s name was Barabbas, a charismatic firebrand who welcomed any & all who wanted to strike out at the Romans where ever they could be found.

j.   Barabbas justified their frequent raids on Jewish travelers to get supplies, saying such people were like dumb sheep, compliantly obeying the Romans.

k.  If they were good Jews, he said, they’d join his band of freedom fighters instead of collaborating with the Romans by living quiet, obedient lives in the comfort of their cozy homes.

l.   At first our thief was uneasy with robbing innocent people, but the voice of conscience was soon silenced by the repeated act of theft.

m. Violence & crime became a way of life.

3.  It would have been the way of his death had it not been for his encounter with Jesus hanging on a cross a few feet away as the last minutes of his life ticked away.

4.  Though his exposure to Jesus was brief and confined within the limits of what the cross would allow, it was enough to open the door of truth to Him.

5.  And realizing the moment and opportunity for what it was – he embraced it, and entered into eternal life.

6.  Here’s the lesson for us: It’s never too late to turn to Jesus!

a.  It’s never too late to turn from your sin and put your faith in Him as Lord & Savior.

b.  As long as you draw breath; as long as your heart is beating & your brain is thinking, there is time for you to repent and believe.

7.  It doesn’t matter if you’re a career criminal who’s strapped to the electric chair or lying on a cot with your arms strapped down waiting for the lethal injection.

8.  If in that moment you genuinely repent, & put your faith in Christ, God will save you.

9.  I recently watched an interview in which a journalist was questioning a Christian about the role of faith in salvation.

a.  The interviewer asked, “Do you believe that a person can live an evil life & then just ask for forgiveness with their last breath, and God saves them?”

b.  When the Christian said he did believe that, the interviewer shook her head and said, “I just can’t accept that – that a person could do all kinds of terrible things during their life, then say some prayer right before they die, and they would go to heaven.  It’s too easy!”

10.Too easy for who???

a.  It wasn’t easy for Jesus!  It cost Him everything. 

b.  We’ll never know how much it cost, to see our sin placed on His cross.

11.     That journalist makes the mistake most do when they think about faith and the role it plays in salvation.

a.  They think Christians believe all a person has to do is ask for forgiveness with their last breath & God expunges a lifetime of guilt.  That isn’t it at all!

b.  What secures forgiveness isn’t a prayer.

c.  Forgiveness is found IN CHRIST.  We don’t believe in forgiveness; we believe in Jesus.

d.  Faith in Him and what He did on the cross is the conduit that bestows forgiveness on us.

12.     When does that forgiveness become ours?

a.  The instant we genuinely believe in Jesus.

b.  Now, here’s the deal – genuine faith in Christ is always accompanied by a heart-felt & sincere turning away from sin.  That’s what we mean by repentance.

13.     Did the thief repent?   Yes! 

a.  Though he wasn’t given much time to demonstrate a changed life, we do see repentance that while he had BEGUN mocking Jesus –

b.  He stopped, rebuked the other thief, then expressed his faith in Christ as Savior & Lord.

c.  If his death had not come that day, we can be sure he would have gone on to a changed life.

B. The Other Guy

1.  As we close, let’s consider the other thief, the one who died that day & found himself in a very different eternity from the repentant thief.

2.  Why didn’t he come to the same conclusion as his cross-mate?

a.  They both witnessed the same thing.

b.  They were both confronted with the same evidence in the example of Jesus.

c.  They heard the same words, saw the same reactions, witnessed the same events.

3.  One mocked to destruction, the other marveled to salvation.

4.  I wonder if the one who refused to repent & believe did so out of sheer pride.

a.  “I’ve been a criminal most of my life. I can’t change now.”

b.  Some men have the twisted idea that it’s noble to stick with the thing they’ve always done, even when they’re shown it’s wrong.

c.  I’ve talked with the elderly who are facing their last days.

1) Concerned relatives or friends have asked that I’ll talk & pray with them.

2) Their loved one is going to be dying soon & they aren’t sure about where they’ll spend eternity –

3) So they ask me speak to them, hoping I’ll be able to say something that will help them find Christ.

d.  Several times, after sharing the way of salvation with them, they’ve told me that they’ve lived their whole lives in this or that religion, in this or that way of thinking.

e.  And now, at the end of life, they can’t just give it all up.

f.   They think not forsaking their previous ways shows integrity, even though they now see their way has been wrong.

g.  No!  Hanging on to error & refusing to repent & believe in Christ is the height of foolishness!

5.  The foolish monkey is the one who refuses to let go of the bauble in the coconut.

6.  And his foolishness will lead to his captivity.

7.  It’s the monkey who let’s go who ends up with the prize in the end.

C. Invitation

1.  I want to end by inviting those who’ve never responded to an invitation to receive Christ to do so today.

2.  It’s not too late for you – nor have you gone too far for God’s forgiveness.

3.  As long as you draw breath, you can repent & put your faith in Christ.

4.  But listen, don’t say to yourself, “This is great.  I can live any way I want, then right before I die, I’ll pray.”

a.  You don’t know the moment or condition of your exit.  You could die suddenly.

b.  And every time you harden yourself to the voice of the Holy Spirit telling you, you need to receive Christ, you become more dull, more spiritually numb.

c.  Today could be the last time the Spirit convicts you.

d.  It could be that if you don’t respond today you’ll lose the capacity to repent & believe.

5.  Don’t let a life-time of holding Christ at arm’s length keep you from an eternity of His love & glory.