Investigating Grace: A Detective’s Case Study on the Thief on the Cross

We trace the thief beside Jesus from likely crimes and arrest to trial, prison, and crucifixion, then turn to the shocking promise of paradise and what it says about grace. Law, guilt, and mercy collide as we ask who deserves a gift no one can repay.

• bandit tactics in Judea and the meaning of lēstēs
• how Romans used informants and undercover work
• swift Roman trials and brutal prison conditions
• the mechanics and purpose of crucifixion as deterrent
• the thief’s confession, Jesus’ innocence, and the promise
• how ancient reciprocity clashes with New Testament grace
• why trying to repay God distorts the gift
• a new community where merit does not rank people
• standing in grace for cops, criminals, and everyone

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Chapters

• 0:00 Setting The Scene And Text
• 1:40 Who Was The “Thief” Really
• 5:00 How Bandits Operated In Judea
• 8:55 How Romans Caught Criminals
• 13:05 Trials, Prisons, And Punishment
• 17:05 The Mechanics Of Crucifixion
• 21:10 From Mockery To Mercy
• 24:15 Redefining Grace In The New Testament

Transcript

SPEAKER_00: 0:00

Welcome to the Cops, Criminals, and Christ podcast. Let's dive in. We have an episode today, like one I promise you you've never heard before. We have Dale, the undercover pastor, with years of undercover police experience and years of pastoring experience and a deep love for the Bible, opening up the Bible in ways you've never heard before. He is going to take a look at the man that died on the cross next to Jesus, what the crime was like, what getting caught was like, what hanging on the cross was like, and how they died, and how he responded and what that means for us today. So settle in, listen, and see what God has for you today. I can't wait to hear more. Like, comment, subscribe, and let us know what you think after you listen on this episode of Undercover Grace with the Undercover Pastor.

SPEAKER_01: 0:47

Listen, this is really fun because I'm kind of fascinated by the different crimes in the Bible, uh, the criminals we meet, uh, the violence we see. And uh one that stood out to me was the story of the thief on the cross. Now, what we're seeing here, it's like we walk into an execution chamber and we're seeing two people getting or three people getting electrocuted at the same moment. And then we're captured. All we know about is we're just capturing the conversation between them. And from them, we're reconstructing what may have happened. I love this because I like digging in and trying to understand the story. And then you're gonna see at the end, just at the end, you're gonna see this cool, you know, like at the end of a murder mystery, and you're gonna see what the reason is, what it teaches us. And it's one deep theological principle that is honestly life-changing. Okay, let's go back and read the story, the little bit we know in Luke 23. Uh, let me read it to you. It is one of the criminals who had been hanged on the cross beside him, verse 39, kept hurling abuse at him, saying, Are you not the Christ? Save yourself and us from death. But the other one, the other thief on the cross, all we hear that is that term. One of the criminals, sorry, one of the other criminals, he says, Do you not even fear God since you're under the same sentence of condemnation? We are suffering justly because we're getting what we deserve for what we have done. So this guy is pleading guilty. And what I'm going to tell you about is the greatest plea deal in human history, okay? Because he is pleading guilty right here. He's saying he's good for this crime. And that's rare. But he says, What we deserve for what we have done. But this man has done nothing wrong. And as he was saying, Jesus, please remember me when you come into your kingdom. And Jesus said to him, I assure you and most solemnly say to you, today you will be with me in paradise. Now, how did that guy get on that cross? That's the question to me. What was it like? What did he get arrested for? What kind of crime would get you on the cross? What would it have possibly been? How did that guy do there? And then he said he was guilty for what he did. And then what about Christ's reaction to him? What does it teach us? So the term here that he refers, that the Bible calls him, is in Greek as Lesti, L-E-S-T-A-I, is a transliteration of that idea. And this would mean that he was a bandit, a highway robbery. And what these guys did was they knew the terrain very well, and you had these rural routes between the big city, Jerusalem, and if you picture Galilee or all through Judea, so picture desert, cliffs, ravines, and these guys would hide a lot of times, not always, but they would hide a lot of times in what was called the Wadi, W A D I, still there. And what it is is basically a dry riverbed. So you imagine when the water's there, yeah, they couldn't hide there. But in the dry periods, they could hide down in that riverbed. And then when the caravans or the or the or the business people or whatever would come around that, they would jump out, grab them, and they would usually use these little small swords. And the reason that's important is because in Ephesians 6, when Paul starts to describe uh what that Roman soldier had, one of the things he had was this little small sword, which is really just a you know, really sharp and dangerous dagger. So they would often carry those. They would stab the person real fast, they would rob the person, and in it they would take everything. They would take caravans, they would take uh livestock, they would take uh cash, and and a lot of times what they love to do, and this is why they could also be seen as revolutionary, is they would wait on a Roman caravan coming through that terrain because the Romans didn't know the terrain. They were there, they're foreign soldiers. It was like our guys in Afghanistan or whatever. The guys in the Mujadin up in the Torabora Mountains, they knew those mountains like the back of their hands. They grew up there. So they could hide, they knew where every dry river bed was. So this is what's going on. These guys jump out, boom, they'd get the Roman caravan, they robbed the Roman caravan. So, in one way, they'd be loved by the Jews because wow, you did it to the Romans. But on the other hand, the Romans would be after them like I don't know what. So they could kind of claim they did it for good, but they really kept the money anyway. I took just some of my detective skills and I was trying to think, like, well, how would we look at this? How would we put this thing back together? And so I just started going back through and reading about these various things. What is the Roman punishment? What were the jails like? Learning all about that, and we can put this together so we can understand who that person was on that cross. He gets up there. Um, I mean, he gets arrested. Now, in order for him to go to the cross, remember it's capital punishment, almost always had to do with violence or some sort of rebuke against the Roman government. It doesn't seem like it's that. He's called in um Matthew and Mark, it's called he's called a rebel. But that term can mean lessa, can still mean bandit or robbery. And the reason we don't think he's a rebel is because, you know, like that he was just anti-Rome or something, is because he says in that verse, it's very revealing what you see, we are suffering justly. There's no way a zealot who is against the, we had the zealots was one of the big groups there. And these guys were tough, brave guys who many of them lost their lives fighting the Romans, the Roman occupation, you know? They weren't those guys. Because they were, they wouldn't say I was suffering justly. They know that that was only made, that cross was really only made for the worst of criminals, violent robberies, murders, things like that. But we also see that the nature of the human being because they're, I mean, one of the robbers there on the other cross is chiding a man who is, you know, a religious guy or whatever they thought of him. And he's chiding him and making fun of him, just like the the uh uh uh Jewish folks were there too, the Jewish leaders were too, as they watched what happened with Jesus, as they saw everything. I mean, they knew he certainly wasn't a murderer, they knew he wasn't a zealot. Everybody had heard of Jesus. By this point, he's three years into his ministry, remember? He was so popular, so known there, that it led to this arrest and his crucifixion. In other words, there was nothing else the Romans could have done at that point. I mean, the Jews could have done at that point. He was going to take all their authority. He had already, remember, he had just come into Jerusalem. We talk about the Palm Sunday thing as though it's just no big deal. No, no, no. It was a massive deal. They were saying he is our king now. So picture you're the Roman, the head, I'm excuse me, the Jewish guy in charge. This guy is literally taking my job. That's the way it was seen. That's how popular it was. So these guys certainly knew that. They knew that he was an itinerant rabbi. They knew that he walked. And and MacArthur thinks that Jesus almost banished illness from Judea and Galilee during those three years, especially during probably two years. That's how many people he healed. He healed thousands upon thousands upon thousands of people. And yet at his cross, remember, there's only two people that we know of that were on his team. So you got evil gods on the ground, the Roman leaders, I mean the Jewish leaders, and they're hollering at him, making fun of him. Can you imagine? And then the two guys next to him um uh, you know, deserved, you know, uh punishment of some sort. And anyway, they're there, and one of them starts uh making fun of Jesus, too. Seems seems uh pretty crazy. You know, pretty evil. Okay, so let me tell you just a little bit more. How did they catch him? That's what I want to know. How would they arrest a guy like that? Like, I know, you know, for us nowadays, shoot, they cheat, in my opinion. The cops nowadays got it easy. They got cameras everywhere, they got iPhones everywhere. It's like you can't even go an inch without. Well, of course, none of that existed. So, how'd they get them? Two ways they caught criminals. And I'm gonna tell you one that nobody likes, but it's something we've all used, and that is snitches. They had to use snitches. How else would they possibly know who the bad guys were, who the good guys were? There is one other way, but I'm just gonna tell you snitches were the big. How did they catch Jesus? Flip Judas. They flipped him, that's what we would call it. They found one in Jesus' circle, close, close, and that's the best informant. Is somebody who's really close to the main guy you want to get, and they got one guy and they found something he wants. That's how you always look for informant. What does he want? Does he want money? Does he want out of a case? What's his angle? Uh, does uh does they want revenge? Sometimes a girl will call us with a boyfriend, they're mad at their boyfriend, and they'll give us, and so they want revenge. So, anyway, figure out what they want, give it to them, and they'll do whatever you want. And that's what they did with Judas. So, in the same way, it is likely these guys also were there because of an informant of some sort. The Romans lived off informants. You're occupying a world. How could you possibly know Jack? You don't even speak the language. Although they did have the Aramaic there that um was common. Okay, so anyway, you got that. Now there's a second way that they caught him, and you'll love this. You'll really love this because my show is the undercover pastor, so this is very exciting. Guess how the Romans would catch him. Go ahead, take a take a guess. Take a guess. You can go undercover, undercover. What they did was this is what we would call tactical work. They would just dress in regular clothes, they would act like they were part of a caravan, and in fact, sneaky devils that they were, they were like we did. Like we would do these robbery details where um we thought the robberies would happen right where we were. And I can think of one night. This one night we're up there, we got guys oppone robberies. We're at the metro at 7th right by the Verizon Center. It used to be the Verizon Center. And we literally, man, we're sitting right there. And while we're sitting there, we watch two of the guys jump out of the car and four stick-up guys grab an old man and they're robbing him and beating him right there. I mean, we're right there, we're on top of it. But they didn't see us coming because we were dressed like this. So we were on them before they could even run away. And we grabbed them, locked them up, everything right there. So that was the idea these guys took. Is they went, they would go in plain clothes and they would sneak around those crevices and act like, oh, I'm just uh, you know, just walking around. And then these guys jump out of the cave. But when they jumped out this time, ha ha, they got grabbed by the Romans. So this guy probably either got grabbed because of a snitch telling on him, like Judas did Jesus, or because the Romans snuck up on him and were in regular clothes. Now, do I know that for sure? Absolutely not. I don't know that for sure. But that's generally the way they caught these guys. So these criminals, let me let me tell you what else. This will help you to understand how bad they were. They would carry um uh those little swords. They're called gladius, the same ones they're referred to in the New Testament, other places. They also might use a sling, like we hear about David Goliath. But imagine some kid, and and I've and I've heard of this going on in in uh where where shepherds, uh, even today, they they would practice rural, very rural shepherds, they would practice this sling because they could wing the the rock or the projectile really fast. And so these guys would use that. And then the other thing they would do, this is kind of troubling, they would use nets or ropes. So they would throw a net down on the people and then bind them. So imagine this is this is why I want you to see how bad this is. If you're in a rural area, let's say it's a dark even, and you are ready, you just lost everything, including maybe your clothes, your water, your food, you know, everything. And you're stuck out there and they keep you alive, but they tie you up. Man, that's that's an evil sucker. Now I was thinking about evil guys who tie people up. We had a uh a lot of times what we would deal with is robberies between dope deal drug dealers who would rob by the drug dealers. And sometimes they make great informants because they would hear about things because they were guys that were always listening for drug dealers holding or whatever. So they would call us sometimes and not admit that they're robbing, but we would always think, like, I wondered. Anyway, there was one guy years ago, he was so evil that when he would rob guys, rob drug dealers, he would bring with him, you know, he got rope. This guy brought with him barbed wire. And he would tie the guys up with barbed wire, just being evil, evil, evil. Anyway, so these guys were bad fellas. This is what happens. They probably got arrested the way we said. Any evidence then would have been caught and captured right then. Now, the trial, this is kind of interesting. There was a trial, actually. But for capital crimes, they might see like a prefect, they call it, or a delegated magistrate. And so the reason this is important is because I wanted you to understand that there was a really different system. But when they went in front of this guy, he was defense attorney, prosecuting attorney, everything. He would just ask questions, he would examine evidence, and then he'd rule right then. The big difference between their capital punishment and ours is there was no appeals, it was done immediately, and then guess what? Their jails, which were disgusting, dark, damp. I think we should spend a whole episode learning about these prisons because prisons make a big part of the Bible stories. There's lots of prison. There's prison in the New Testament where Paul and Peter went, the apostle went, you've got prison back in the Old Testament, Joseph for 12 years he was locked up. But to understand, you know, what they went through, but these prisons were made not for long term. They were made for quick and really awful punishment, but they were cramped, crowded. They left them in their food and their waist, left them in their own waste because there was no bathrooms for them or whatever. They were always crowded, too crowded. And uh and then they got little food because they only gave them food, get this, to keep them alive to execute them. They only gave them enough food to keep them alive to go kill. So by the time they got to the cross, they must have been in terrible shape, you know? Even if they were just there a few days, though. I'm thinking of a few days without much to eat and drink, and you're crammed up with those guys, and you're going to the bathroom, and they're going to the bathroom. And I mean, it really was awful. There's a lot of beatings, too. I've never done corrections. I've I've I've certainly been around them. We serve warrants at the at the DC jail. And then as a pastor, I've been in more jails than I have as a policeman. And um yeah, there's there's just a lot of violence in those places, certainly from both sides. You know, it's a violent place. These are violent people. So, anyway, so this is what happens. He ends up on the cross. Here's the amazing thing. After all of what I just told you, the drum roll is this guy, as he says, remember, he says, I deserve this. Generally, we don't say that about ourselves unless it's pretty bad, you know. So, I mean, I he deserved that. I mean, come on. Because understand what happened here. You got a beating before you went on. Most guys died at the beating if you really went as far as they did with Jesus. But they crucify him. When they crucify him, the idea is the the nails, these long, you know, nails would go into a wooden like a tree, where it'd be more like a T type thing. But anyway, it had to be here instead of here because it would just rip through, the nail would just rip through the flesh here. So it's here to hold them in place. Okay, now the way they really died, and the point of the cross was they wanted it public. The Romans wanted public to tell them don't rob us, don't rob other people, don't kill other people. And it was to be used as a deterrent. And so imagine that other people could see this, and it went on, guess what? Days because they they couldn't die fast enough. The body didn't die always fast enough. Jesus died within nine hours. But these guys, what it was was the way you stayed alive was you started slipping on this, and and it you would suffocate on your lungs. So you'd have to pull up on those nails to breathe and grab a breath, then you go, then you grab a breath. Let me tell you one interesting thing. It was it was very common for murder, and it was this is an interesting part, a lot of interesting things about crucifixion, but it was created by the Romans, and um and and it was predicted by Jewish prophets years before it was ever invented. Fascinating. Read Psalm 22, and it's like word for word, and nobody even knew what this was. It would be like me talking about the electric chair in the I don't know, 1700s. It didn't even exist. How could you possibly do that? So, anyway, that that's one. Two, crucifixion. Let me tell you about it. Okay, this is really awful. 35 years later, remember the Jewish leaders that are in front of Jesus, catcalling him, saying things, and they're the ones who put him on the cross. Okay, about 35 years later, AD 70, Jerusalem falls to the Romans. The Romans, uh, Jesus predicts this, Matthew 24 and 25, in quite a bit of detail. But anyway, the Jews didn't listen to Jesus, of course. And so the Romans came in and they decimated uh Jerusalem. They flattened the temple completely, like where Jesus said there won't be one stone on the other. That's how bad this devastation was. And they starved him out. And then the other way they did was they crucified him. And they crucified so many people. They crucified all the Jewish leaders, all the Jewish people. So here's what I want you a picture. I don't know, I don't speak for the Lord. Nobody knows this, but you gotta wonder if a man was in his 30s when they when he was a Jewish leader and he crucified Jesus, was he still alive? And then was he crucified himself? They crucified so many Christians, they crucified so many that they ran out of wood. The 8070 was just brutal, horrible. And it was, yeah, the evil. Another interesting thing for us to study that whole deal. But anyway, so so this is a this is the moment. This guy's suffering, this guy's evil, and then we have this conversation where he says, Jesus, remember me when you come into your kingdom. It's interesting. You want a pardon, you want a plea deal, you want to work this out so you don't end up getting what you deserve. And so guys come up with all kinds of requests to try to make this right. But this dude, mostly they do that to save their own skin. This guy apparently was for real. He was serious. And Jesus responds in a way that I want to teach you. Now, this is the big, huge lesson that Jesus was teaching us. In this story, what do we really learn? What do we really learn? How bad bad guys are. Maybe we learn that um about Jesus' forgiveness, certainly. But there's a there's a component of Christianity that is unlike any other faith, and it surrounds this word grace. Now, the word grace in the New Testament is cherished, C-H-A-R-I-S. This idea to the Greek was something they all knew what the term meant. But this is what the term meant. If I gave you a gift, that was grace, it was socially binding. So, Christian, if I gave you a gift, you would owe me and we would be socially reciprocal, is another part of it. You would have to give me back something. Um, it was immoral to give, this is very important. This is very hard for you to understand because you don't think of grace this way, the way you thought and heard and all. Grace to them was it was immoral to give it to a person who didn't deserve it, who didn't have your worth. So picture this. Maybe it'd be similar to us going in business and and going a businessman at a country club and walking out and uh grabbing a bum and bringing him in. This would be socially, you know, horrible for you. You wouldn't do that. And it was embarrassing, it was socially dangerous for you to give a gift to somebody who wasn't of a certain worth, a certain value already. You know where I'm going, right? You see where this is set at. So Paul comes along, and Paul later in describing this idea, he had to respond to this. And what Paul did was he explained this grace in an upside-down way. What does he say? Think about this. Christ died for who? The ungodly. So he dies for this thief, this bum, this robber. Paul's grace redefines it's unearned, it's completely incongruent to what happens. It's given to the unworthy, not to the worthy. It can't be paid back. One of the things I was just listening to John McCa, excuse me, John Piper talk about this. It's very helpful. He talked about this. To you and I, we might say, we owe God. We owe God. We're obligated because of this grace he has shown us, and we're going to try to pay him back by giving, by living a godly life, by obedience. Well, this is a horrible, horrible distortion of grace. Why? Because grace has got to be given to someone who cannot pay it back. It's so good. How could you ever pay it back? So it's insulting to me. If I if you give me something really great and I try to pay you back, what am I gonna do? Pay you back with tic-tacks after you gave me a full meal? Oh, what can I possibly offer? Second part of this gift is really good. If I try to pay you back for grace, then I've insulted the giver. Here's what I mean. You have me over for dinner. And I don't think you've ever had me over for dinner, but if you had me over for dinner, if you ever offered me a meal, I think it's a one-way street. I offer all the meals in this in this relationship. So if you I offer, you offer for dinner. We go over there, maybe you give me peanut butter and jelly sandwich, okay? At the end of the peanut butter and jelly sandwich, I say to you, um, uh, thank you for this meal. I will give you a meal of peanut butter and jelly sandwiches, the same on Tuesday of next week. Now we're even. You would say, Why did I even give you this sandwich then? I wasn't giving it to you because you were going to give me right back. That's again insulting to the giver and to the gift. This was the idea that Paul was trying to explain. It is so important. And this is the big one, and I'll leave you with this. That guy on the cross, picture him. Bad guy, robber, knew he deserved it. Says to the one who doesn't deserve it, remember me in paradise. And right then he gets grace from the savior, not based on the worth of the recipient. Two things the gospel does. This is very important to anybody who's ever done anything wrong, which we all have. But whether you're a criminal or a criminal by our courts or whatever, you're in jail, or you're a little old lady, you know, who's nice to everybody and helps uh, you know, neighbors or whatever. Either way, the Bible says something fascinating. He levels out the unworthiness of all human beings because he says there is none righteous, no, not one. It's very offensive. We say, You can't compare me. I'm righteous compared to this guy. None righteous, no, not one. All of us are the same, all of us have broken the Ten Commandments. So in one way, we're the same. I know I'm not the same as a murderer, but in God's eyes, we've all broken his commandments. Okay, so that's one. He evens that out. Then the second thing he does is he evens out the recipients of grace. And he makes a point, if you remember passage, 1 Corinthians 1, uh 15. Remember when he says uh 26 to 29? Remember when he says you were unworthy as some of you once were, ignoble, uh, not rich, not and then get this. Here's the other cool thing about grace. Grace started a new community that couldn't have existed before this. Here's what I mean. In the new community of grace, Paul takes great effort to explain neither slave nor free, woman or man, okay, criminal or not criminal. It doesn't matter. There's a whole new community that just started. Boom. This whole new thing that started. That's why the Christian sees it all. We're all under the grace of God. So I don't have anything better than the guy who's uneducated because I've got a little bit of an education, not much of one, but I've got a little bit of education. So I'm no better than the guy who has no education. And and the guy who has uh Harvard degrees, a guy told me today we're in a meeting, he told me that he had three doctor's degrees. And I was trying to think, you know, I'd just been thinking about this grace thing. So I thought, you know, we're all the same, buddy. We've all received the grace of God. We're only getting into heaven because of his grace, not because of your degrees or mine. So anyway, I think it's really exciting. And I think it's exciting to think that a guy who's hiding down in some riverbed robbing people and killing them is going to be in heaven next to me because of why? The wonderful grace of God. To the Christian, I'm going to tell you something really cool. Romans 5, 2 has a phrase in there that I really never noticed before, stand in grace. And what he's teaching him here is because grace unearned, like you're not worthy to ever receive it, can't be paid back. I want you to live differently. I want you to stand. The Greek idea here is come into a new country. Come into a new realm, this realm of grace. It's a whole new country. It's a country where, unlike your job, unlike your relationships, unlike all that, you can't pay it back. And don't try. You are unearned, but you are loved and you have been taken in, and you can live in this grace of his forgiveness, and you must believe it, and you must adapt to it and adopt it because it is so wonderful and it is insulting to not. That's why you got to stand in grace, live in grace, live guilt-free, and so on. Okay, it doesn't mean you don't deal with your sins for heaven's sakes. Of course you do. If you're a real Christian, you wouldn't standing in grace doesn't mean that you love sin. No, just the opposite. That's exactly what second one is the criminal. The criminal, well, this story's for you, uh, as much as all of us are criminals, like I just said. He says, man, he says, Paul said, God proved his unlimited patience because he saved me the chief of sinners. And so Jesus, I don't care how bad you are, criminal, wherever you are in prison, you've you've been convicted, you're released, or maybe you've never been arrested for something you've done. Oh, you gotta know this grace is for you, man. That's what he designed it for. And that's why he used as our as our point this really horrible person who leads this whole grace movement is an evil murderer himself, Paul the Apostle. He's the leader of it. He's the one who explained grace. This is the first one to really explain grace. Okay, so the criminal is gonna be good as long as he does what this guy did. He turns to Jesus and he calls out to Jesus, please save me, Jesus. Nobody else could save him. I'm a sinner, I deserve this. Be honest with God and beg him for salvation, and you'll get it. The cop needs to see. I always say this to the cop, so he needs to see that he's no different than the criminal. He's no different ultimately than the criminal. It doesn't mean that he shouldn't enforce the law. He should. It doesn't mean they shouldn't sneak around and catch bad guys. Doesn't mean he shouldn't use informants. All those things, fine, great. But understand that but for the grace of God, but for the grace of God, I deserve as much punishment as any criminal I've ever arrested. And that's for sure.