The Right and The Left of The Middle Cross

July 19, 2026
The Right and The Left of The Middle Cross

Two criminals were crucified beside Jesus — and at first, both of them cursed Him. So what changed? In the last agonizing moments of his life, one of them saw something the other never did, and with nothing to offer but a dying breath, he was ushered straight into paradise. The first person Jesus welcomed into heaven wasn't a saint or a scholar — it was a convicted criminal. And that is the best news you've ever heard.

Continuing the "People That Matter" series, Kerry stands at the foot of the middle cross to unpack the two men on either side of Jesus — one who rejected Him and one who repented — and the staggering grace that saves us by faith alone.

In This Message:

  • Jesus "numbered with the transgressors" — the friend of sinners who died between two criminals
  • Both robbers first rejected and mocked Him — no one is beyond hope
  • The repenting criminal's epiphany: "This man has done nothing wrong"
  • "Today you will be with me in paradise" — grace with no works to boast
  • The assurance that when you step into Christ, you're already in

Key Takeaways:

  • You and I are the transgressors He died for — He was numbered with us
  • Salvation comes only through the cross, never through our own goodness
  • The first step toward God is a holy fear that leads to repentance
  • Heaven is a free gift of grace received by faith — not something earned

The Challenge:

Stop trusting the "pretty good guy" inside you. Your best works are filthy rags next to God's holiness. This week, surrender all to Christ and rest in His assurance — the moment you step into Jesus, you're in, for eternity.

Scriptures Referenced: Luke 23:32-43; Matthew 27:38-44; Mark 15:27-28, 32; John 19:18; Isaiah 53:12; Luke 5:30-31; Mark 2:17; Matthew 9:12-13; Romans 5:8-9; John 14:6; Luke 1:1-4; 2 Timothy 4:11; 2 Corinthians 5:21; Galatians 3:13-14; Luke 7

You know, we started a sermon series a couple of weeks ago entitled Those That Matter. And Simon of Cyrene, the cross bearer, we studied him and the call in that was take up your cross and follow me. He was the first cross-bearer. We learned that probably he came to Christ because there's evidence that his two sons and his wife became Christians in the New Testament. And so when he went back, he was from Africa. And when he went back to Africa, he probably had to share the gospel with his kids and his wife, and they came to Christ. We talked about the daughters of Jerusalem, the cross mourners, the lamenters, and how Jesus said, you guys quit weeping for me. Weep for yourselves. Take your focus off of me and focus yourselves on your own depravity so that you can come to me. today we're going to look at the right and the left of the middle cross the right and left of the middle cross and I'm going to read verses 32 through 33 to set up our lesson today so I want you to I think they've got it on screen maybe verses 32 through 33.

And two others also who were criminals. Some of your Bibles may say in other Gospels, thieves. Now, the best English word that we could translate for this was bandits. They were not petty thieves. These were violent criminals. They would steal, but they might also pillage and rape and destroy everything also. They were bad guys. They were not good people who were criminals, were being led away to be put to death with him. And there's no way of showing this, but some biblical theologians say that they might have been partners with Barabbas in the insurrection. I can't prove that or not, but I thought, what an interesting thought to think maybe they were connected with Barabbas.

To be put to death with him. And when they came to the place called the skull, Kim and I have been over to Jerusalem. In fact, when I was up in Gruver this week, I talked, you know, we'd just been there a couple of months, and Carly Knight called us up front and said, hey, we're going to give you a trip for Christmas. Yes, your Christmas present. And I'm going, I've never had a church give me a Christmas present. And so I thought maybe they're going to give us $50 or $100. They said, here's your ticket to go on the trip that the conference is taking to the Holy Land. We're sending you to the Holy Land. I remember Kim and I were amazed. We said, y'all don't even know us, and you're already sending us to the Holy Land. It was an amazing trip. The bishop and district superintendents and preachers went and only two late couples went and one out of our church Barbara and Delano Kluck went with us And what a great time we had together in Israel But you could see, we could sit there and look across and see the skull. You could just imagine where Jesus was crucified. There they crucified him and the criminals. one on the right and one on the left amazing that I came up with that for a sermon title wasn't it the right and the left of the middle cross Jesus was crucified with two criminals bandits Bill being an officer he'll laugh when I thought when I hear the word bandit I think of banditos the banditos we all have that concept in our mind of the West Texas banditos in Matthew 27 38 it says at that time two robbers were crucified with him, one on the right and one on the left. In Mark 15, 27 through 28, it says, and they crucified two robbers with him, one on his right and one on his left. And then it says this, and the scripture was fulfilled with says. This is a very important statement. It comes straight out of Isaiah 53, 12. And he was numbered with the transgressors.

You see who God's putting Jesus alongside of? Transgressors. Transgressors. In John 19, 18, it says, There they crucified him. And with him, two other men, one on either side, and Jesus in the middle, in between. Now, guys, I think it's significant that all four Gospels root within the crucifixion of Jesus that two criminals died on the side of him. It is what I call the atoning connection that he was the friend of sinners. Do you hear that? He was the friend of sinners. This eternal theme runs throughout the very veins and life-giving blood of Christ. In Luke chapter 5, verses 30 through 31, it says, and the Pharisees and the scribes began to grumble at his disciples saying, why do you eat and drink with the tax collectors and sinners? Interesting, they didn't direct this question to Jesus. They didn't have the guts enough to. They just asked his disciples. But Jesus overheard and Jesus answered and said to them, it is not those who are well who need a physician but those who are sick. I have not come to call the righteous, but sinners. Sinners to repentance In Mark chapter 2 verse 17 in Matthew 9 12 he also says the same thing, but he added this challenge. I want you to hear this. But go and learn what this means.

I desire compassion, not sacrifice, for I did not come to call the righteous, but sinners.

And he was numbered with the transgressors.

Now, I don't want to insult you or hurt your feelings, but guys, that's us. That's us. We are the transgressors that he died for. In Romans 5, verses 8 and 9. The apostle Paul,

the chief of sinners, said, but God demonstrates his love for us. And while we were yet sinners,

Christ died for us. We hadn't even made any movement toward God. While we were yet sinners, Christ died for us. Much more than having been justified by his blood we shall be saved from the wrath of God through him.

In John 14 6 Jesus said no one comes to the Father but through me.

Only through the cross. Only through the cross.

And he was numbered with us.

Now if that shouldn't stir your heart up, I don't know what would. Jesus was numbered with you.

He's not a part of just that religious establishment.

He's not separate from us as the Son of God. He is the Son of Man that was hung on the cross for you and me. He was numbered with us right between those two criminals.

Two men.

One on the right, one on the left. Of the man on the middle cross.

One rejected and one repented. I want you to see that today. I want to talk about the rejecting man for just a second. In verses 35 through 39, it says, And the people stood by looking on, and even the rulers were sneering at him. He saved others. Let him save himself. This is the Christ of God, his chosen one. It's interesting here that they use messianic titles to identify him. They don't even know what they're saying. They're speaking the truth right there. He is the Christ of God. He is the chosen one. And the soldiers also mocked him, coming up to him, offering him sour wine and saying, if you are the king of the Jews, well, he is, but if you are the king of the Jews, save yourself.

Now there was also an inscription above him, this is the king of the Jews. And one of the criminals Who were hanging there Was hurling abuse at him and saying are you not the Christ Save yourselves and us You know, if you're so hot, well climb off that cross, save yourselves and save us.

In Matthew 27, 39 and 44, it says about the same thing, except he added a little more information and it's very profound information. And those passing by were hurling abuse at him, wagging their heads and saying, you who are going to destroy the temple and rebuild it in three days. Remember when he said that? Save yourselves. If you are the son of God, come down from the cross. This was the height of insult to Jesus. In the same way, the chief priest also, along with the scribes and elders, were mocking him and saying, he saved others. He cannot save himself. He is the king of Israel. Let him come down from the cross and we shall believe him. He trusts in God. Let him deliver him now if he takes pleasure in him. For he said, I am the Son of God. In verse 44, I want you to hear what this says though. That's why you need to read the other gospels sometimes. And the robbers, plural, and the robbers also who had been crucified with him were casting the same insults at him. Mark 15, 32 verifies that. And those who were crucified him were casting the same insults at him.

Initially, right off the bat, both robbers were rejecting him. Now I want you to catch that. Both. Both were hurling insults at him. In their last moments, in their own suffering, their own beaten, bloody, and suffocating bodies. You know, it was suffocation that ultimately killed them. When they put them on the cross, they sagged their knees and so it put pressure on their lungs and so the only way they could live was to pull themselves up by those nails in their hands and breathe in and then let back down and then when they needed a breath up and down that cross beaten and bloody their backs lacerated up and down pulling up and down to breathe you know it talks about how they would sometimes out of mercy they would break their legs so they couldn't pull themselves up. They were going to break Jesus, but then the Bible says, no, they didn't break his legs because he was already dead. And they pierced him with a spear into his pericardium where water and blood came out just to show that he was dead. So they did not break, and that's fulfillment. They didn't break his legs. Maybe they broke these guys legs, I don't know. Maybe they did when they came there, probably.

Initially, I want you to hear that, both, both.

Both of these robbers were rejecting him in their last moments. The reason I want you to see that condemning posture of both is because of what is coming.

Next, it is so mind-boggling to me.

It's beyond comprehension.

It's absolutely amazing. The repenting man.

In verses 40 through 43. And I'll explain this in a minute. But only in the gospel of Luke is this recorded. But the other answered. At some point, after hurling insults, the other criminal answered and rebuking him, rebuking the other criminal said to his partner in crime. I'm sure they probably were friends. do you not even fear God since you are under the same sentence of condemnation?

And we indeed justly, for we are receiving what we deserve for our deeds, but this man has done nothing wrong. and he was saying, Jesus, Jesus, remember me when you come into your kingdom.

And Jesus said to him, truly, assuredly, I say to you, today you shall be with me in paradise.

Now this conversation, I already stated it, was only recorded in the Gospel of Luke. The other guys make no mention of this conversation.

They share that both criminals were hurling insults.

Do you remember how the Gospel of Luke started when we started in the very beginning? Let me read verse 1 through 4 in chapter 1. In as much as many have undertaken to compile compile an account of the things accomplished among us, just as those who from the beginning were eyewitnesses and servants of the word have handed down to us, it seemed fitting for me as well, having investigated, he's a doctor, investigated everything carefully from the beginning to write it out for you in a consecutive order most excellent Theophilus so that you might know the exact truth about the things you have been taught St. Luke was a doctor an investigating doctor an interviewer of eyewitnesses and the Holy Spirit. It wouldn't be in here if the Holy Spirit hadn't put it in here.

I got to thinking about that How come he records this and others don 2 Timothy 4 says the Apostle Paul writes this, only Luke was with me.

This was on Paul's final missionary trip.

Guess who was his sidekick? the guy that wrote the gospel of Luke.

Only Luke was with me. Luke was a constant companion of Paul's and had ample opportunities to interview eyewitnesses of the crucifixion. the story of the repenting criminal about the last moment of his life were probably from an eyewitness Luke interviewed or at least one that had heard the testimony of an eyewitness. Yes.

Luke was the only one traveling. He had ample opportunity as he was putting this gospel together to come up with that story. And I don't think it's one he just made up, guys. I think the Holy Spirit put it in there to show us one rejecting Christ, one repenting. and coming to Christ while hanging with him and beside him. What created this epiphany? That's the only word I can think of. What created this epiphany in this repenting criminal?

Could it have been when he heard them saying, he saved others he saved others that's an actual true statement isn't it could a light come on then I don't know I can't tell you could it have been when he saw the sign over Jesus that proclaimed the king of the Jews that a light came on I don't know But the phrase that really got me was when he said to his partner in crime, this man has done absolutely nothing wrong.

Now, you've got to sink your teeth into that statement. It just didn't drop out of the air into his heart. could he have known more about Jesus than what meets the eyes right here?

This man. We're guilty. We're guilty. We deserve what we're getting. But this man, this man that's in the middle of us, he has done absolutely nothing wrong.

I have a sneaky suspicion that that criminal knew a little bit more about Jesus because of that statement He knew Jesus was innocent Where had he been through all the mock trials What he had been saying? What he had been hearing while he was in prison? What was the drift that was going on? Had he been before he got arrested, seen Jesus do miracles, heard him do some teachings? Where had he been? We don't know. We don't know. But for him to make the statement that this man did absolutely nothing wrong, it's got to make you think and come up with some conclusions. I came up with my own, but. So what do we know about this repenting criminal? I just listed these things real quick. He confronted his friend with the truth. he did not want to go to hell and I don't think he wanted his friend to go to hell do you not respect God do you have no fear of God you know J.D. Walt one of the guys that Kim and I listened to early in the morning made the statement, friends do not let their friends go to hell.

You hear that statement?

Friends do not let their friends go to hell.

He's rebuking his friend, hopefully that turned the light on inside of him also. I think we can say he feared God.

You know what I've learned when I've worked with people that are coming to Christ that the first step to knowing God is fear. I'm not talking about being afraid. I'm talking about respecting the sovereignty of the almighty God. that's what we call the conviction of sin when the Holy Spirit comes upon us when the Holy Spirit fell on me the night I got saved I wasn't shaking in my boots but the thought of going to hell did pass through my mind and I can remember thinking I don't want to go to hell I don't want to go to hell I think we can say this man feared God. That he went through his own repentance at that point. That he acknowledged his sinfulness.

He acknowledged he was guilty, didn't he? We're guilty. He said to his friend, we're guilty.

We're sinful. he cried out to Jesus.

You can't take that out of that story, can you? He cried out to Jesus.

It implies here that he pled for mercy.

He recognized Jesus. When you come into your kingdom, he recognized Jesus as the king. When you come into your kingdom, remember me. and he got a lot more than what he asked for Jesus said today that's pretty immediate today today you will be with me in paradise that word paradise comes from a Persian word which is about just the garden of pleasure And in the Septuagint, when they converted that word to the Greek word, it referred back to the garden of Eden. The garden of paradise.

He received the gift of heaven. No, that's kind of mind-boggling to me.

The first guy to go into heaven was a criminal.

Does that blow your mind?

In Luke chapter 7, I think it is, it says that Jesus is a friend to sinners. he is a friend of sinners in 2 Corinthians 5 I want to read a couple of scriptures to you and then I want to tell you a story God made Jesus his only begotten son who knew no sin that man say about it, he's done nothing wrong to be sin on our behalf that we might become the righteousness of God.

Galatians 3, 13 and 14.

Christ redeemed us from the curse of the law. Having become a curse for us for it is written cursed is everyone who hangs on a tree. That's where we shall have all been on that tree in order that Christ Jesus the blessing of Abraham might come to the Gentiles you and I are Gentiles so that we might receive the promise of the Holy Spirit through faith.

I'm glad that Luke completed the rest of that story. Or we would have just seen two guys on the right and left of Jesus going to hell. but one of them repented got saved and went to heaven now I'm going to tell you a story I laughed the first time I heard this story because I never thought of it in these terms and it's a story that's been told in many pulpits it's not original with me and when I started somebody would go oh I've heard that story but it's a story that walks and talks every time I tell it every time I think of it this criminal that repented went to heaven and he came to the gate and was making his entrance in and some of the disciples were there and going wait a second you never went through any formal training in a class on how to become a Christian

You never went to Sunday school.

We doubt you ever even went into the temple. You're just a criminal.

You just don't belong up. What are you doing up here? What are you doing up here? Who said you could come up here?

And he just looked at them and said, the guy in the middle told me I could come up here.

The guy in the middle told me I could come into heaven.

He is the king of heaven.

And he is in charge of who comes in. and he told this guy who had no righteousness to boast, no works to share no reason that he could say I'm worthy enough to come in he told this guy today you will be with me in paradise

Now I don't know about you, but I'll say this about me.

Sometimes I think, I've thought, well, I'm a pretty good guy.

I'm a pretty good guy.

Well, he'll let me into heaven because of that.

Well, I'm good as the next guy down the road.

And then he reminds me.

The best you have to offer, Kerry, are as filthy rags to me.

The best work you can ever do the most love you can ever give will never measure up to my standard of holiness.

Repent and come to me And when he says the word assuredly there truly let me tell you what that means, without a shadow of a doubt.

I'm making the statement. I'm making it factual today. today you will be with me in paradise guys I'm already in heaven you hear what I'm saying the day I accepted Christ I stepped from this world into the kingdom and I have no doubts because I'm already there.

When you stepped into Jesus,

you have no fears because the King of kings says, you're in.

You're in for eternity.

Amen Let bow together in prayer Lord these people really mattered that we been looking at because they teach us such deep spiritual truths.

Lord, I pray today for anyone in here that might not have ever come to you that today they will say, Lord, I surrender all to you.

I pray for those that are shaky about the assurance of knowing that they are a child of God, that they'll put away any idea that they could ever earn it, that it is a free gift of God by his grace through faith. That you will give them assurance of their salvation.

Lord, we learn a lot from these two guys.

I'm glad I'm on the repenting side.

In Jesus' name I pray. Amen.