The Penitent Thief, Hope in Hopelessness

The Penitent Thief, Hope in Hopelessness February 26, 2024

The Penitent Thief speed painting created by the author
The Penitent Thief “speed painting” created by the author

If you really want to understand hope in hopelessness, you need look no further than a man on a cross. While ultimately all hope is found in Jesus, today, I’m not talking about him at least not directly. Rather, I’m talking about a man we only really know for his sin. I’m referring to someone Bible commentators sometimes call the penitent thief.

His story is found in Luke 23:39-43.  This man is mentioned in all four gospels, but never by name. We’re simply told he was a thief or a criminal—one of the men crucified on a cross next to Jesus. 

The Other Thief

To one side of our Lord was thief who reviled Jesus, saying, “Are you not the Christ? Save yourself and us!” Basically he was saying, “If you’re really who you say you are, prove it! Save yourself and save us!” His assertion is “You can only be the Lord, if you can get me out of this struggle. If you do this thing my way, you can be Lord. 

How many people act that very same way? I mean this is pretty much why Jesus was on the cross from a human perspective. If Jesus wasn’t going to get Israel out from under the thumb of Rome, He wasn’t the Messiah they wanted, and if He wasn’t the Messiah they wanted, then to them, He wasn’t the Messiah. He would be thrown away, and they would look for someone else. There is a huge lesson in this for us.  

Are We Any Different?

So many people approach God saying, “If you’ll stop my pain, if you’ll heal my body, if you’ll solve this problem, or get me into this relationship, or get out me of this mess, then you can be God of my life.” The thing is, if God can only be God if He does things your way and in your timing, He is not God in your life, you are.

Consider Jesus

If God can only be God if things are good, no one has a bigger complaint than Jesus. Jesus is God, the second person of the Trinity, and He did live perfectly and still He found Himself on a cross. He did it because of His love for you and me. For this first thief, God can only be good if his life is good, and if you find yourself in that place, with that attitude, you’re in the danger zone.

The Penitent Thief

The other thief heard what the first man said and replied,Don’t you fear God,” he said, “since you are under the same sentence? Now I don’t know how he could see it, but this man seems to be having a sudden dose of clarity. He knows who he is and what he has done. He knew the penalty when he committed the crime, and now he is paying the price. He is guilty and he knows it. 

Crime and Punishment

Hearing this other thief (and I always wondered if these two had been partners in crime at one point) railing at Jesus, as if this thief is innocent and doesn’t deserve his penalty, the penitent thief rebukes him. We are punished justly, for we are getting what our deeds deserve. But this man has done nothing wrong.” Somehow, and I don’t know how, this man knows Jesus is innocent and suffering something He doesn’t deserve. 

Do We Do That?

The first thief seems to be blaming his condition on Jesus. And we see that a lot in our world, don’t we? We see people saying, “If God is so good, why do bad things happen?” Understand what that is. That is blaming evil on the only One who has nothing to do with evil. The perfect God is not the cause of any evil. Evil entered the world with sin. Evil came along when people chose sin over God. Does that mean every suffering person deserves their suffering? No, but neither does God deserve the blame. Why is the bad stuff somehow always “God’s fault?” Meanwhile we take credit for the good stuff, as if to say “Look at all my accomplishments. I did that.” 

It’s this simple, the Bible reminds us that the wages of sin is death and all have sinned and fallen short of the glory of God. We are all guilty. When we struggle, we can take the penitent thief’s words to heart. We are punished justly, for we are getting what our deeds deserve. But this man has done nothing wrong.” The consequences of our actions are not God’s fault, they’re ours. Jesus has done nothing wrong. Conversely, He has done everything right. 

Hope in Hopelessness

I don’t know how he knows it but he does. This dying thief, looks to Jesus and says, “Jesus, remember me when you come into your kingdom.” Jesus answered him, “Truly I tell you, today you will be with me in paradise.” I think a lot of people see this story wrong. They look at this thief and say, “Well if that thief can get in, having done nothing to deserve salvation, then anyone can get in.” No, that’s not how this works. 

First of all, there is nothing we can do to deserve salvation. Salvation is a gift that Jesus bought at a high price. Grace isn’t cheap. It was very expensive. So expensive we could never have earned it, but a gift is not a gift if you have to pay for it. God gives it freely, and we just need to receive it. Only the sinless eternal Son of God could save forever, and so only He could pay your price and mine, and only through faith in Him are we saved. 

Jesus went to the cross and took what our sins deserve, so we could place our faith in Him and receive what only He deserves—eternal life in heaven. Some people act like this thief got off easy. He didn’t have to do so many of the things the rest of us. are called upon to do. He said a few words to Jesus and He was saved. “Today you will be with me in paradise.”  Folks it’s not about the words the penitent thief said. It’s what’s behind the words that saved him. 

Think About Jesus

Consider the reactions the people had to Jesus throughout His life. Jesus fed the five thousand with five loaves and two fish, and the next day He told the people He was the bread of life, and most of his followers abandoned him. 

Jesus cast out a legion of demons from one man. Because of this, for the first time in many years this man, who terrorized everyone around him, was now sane and in his right mind. Many people saw Jesus do this, and what was their reaction? They asked Jesus to leave their area. At another time, Jesus cast out demons, and people said He cast them out by the prince of demons.

Jesus healed some people of life long diseases and the religious leaders wanted to kill Him because He did it on the Sabbath. Jesus gave sight to the blind, hearing to the deaf, and cleansed lepers, but He had to tell those people not to tell anyone because He didn’t want to do battle with the religious leaders before the appointed time. Sometimes no good deed really does go unpunished.

Jesus raised a man from the dead, and the religious leaders of the people determined to kill both Jesus and the man Jesus saved because they feared that the people would come to believe in Jesus as a result of seeing this “dead man walking.” 

Jesus fulfilled over 300 prophecies in His life, the odds against anyone being able to do that are nearly as big as the universe itself, and after seeing all of that, relatively few people believed in Him, and the fact that He is the Messiah. The Scriptures foretold it from the beginning and even that persuaded almost no one that He was their King. 

Think About the Penitent Thief

Now consider that this man, this thief, hanging on the cross, having experienced everything that Jesus was experiencing, living through the same agony, realizing that death would be the end of this sentence. Still even in spite of all of that, This penitent thief looked over at Jesus and still believed that Jesus would have a Kingdom. 

Folks. this man who we only know by His crime, this thief, has just demonstrated one of the greatest acts of faith recorded in Scripture. This dying thief had more faith than most of the people of His land. That’s what saved him, the same thing that saved you, if you are a believer. One word—Faith. Without faith it is impossible to please God.

How You Can Find Hope in Seemingly Hopeless Situations

Think about this thief. That very day, he died and entered paradise. He is there to this day. Jesus declared it and I believe it. He didn’t get the chance to do most of the things we expect Christians to do. He didn’t get baptized or go to church or give or serve or anything else. He couldn’t. It was too late. He was nailed to a cross. It was his faith that saved him. And so it is with us. Those things I listed above are not what save us. They are actions of obedience to the One who saved us. 

This thief, in the midst of horrible suffering, could look at Jesus, even in his hopeless state, dying right beside his Savior, and still believe Jesus could have a kingdom. This thief believed that. Do you?

You see, we look at our world and see the things that are wrong and sinful and, dare I say, terrifying. It can be really easy to lose hope. It can be really easy to see things as hopeless. It’s in those moments when we who believe need to look past the hopelessness and look to Jesus, just like that thief did.  We need to look to Jesus, and believe He will still have His Kingdom, because He will. He has yet to break a promise. 

His Kingdom is coming, in fact it is already here. May His will be done. 

This post is an excerpt from a recent sermon. You can hear it here. 

I also made a brief based video on the passage for a friend’s Stations of the Cross group art exhibition.

About Dave Weiss
Dave Weiss is a pastor and a traveling speaker. He has written and/or illustrated many self-published books and has his MDIV and DMIN, both with a concentration in Creative Arts Ministry. He is married to his wife Dawn and has two adult sons and a grandson named David. You can see more about his ministry at You can read more about the author here. You can read more about the author here.

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