Luke mentions that one of the criminals taunted Jesus, demanding him to save himself and them who were crucified with him (Luke 23:39). The second criminal, however, rebuked the first, telling him he had no fear of God, before whom they both were coming to be judged (Luke 23:40). The second man admitted to his guilt, saying that both his and the other man’s judgment fit the crimes they committed (Luke 23:41).
This man then turned his eyes upon Jesus and asked him to remember him, when he came into his Kingdom (Luke 23:42), which is the practical application of the theology mentioned in Romans 10:9-10. It seems, though, we tend to give this man unwarranted theological understanding. He is not a theologian; he is a criminal who, though he may have met Jesus prior to their meeting here, was not one of Jesus’ disciples. Prior to this occasion, he had never placed his trust in Jesus. There is little doubt his sentence concerned crimes of insurrection against Rome, something Jesus would not have commanded. Yet, at this time he asked Jesus to remember him, as though he realized Jesus would rise from the dead. What should we make of this? It might be better to understand what Jesus made of it.
Jesus told the man who asked Jesus to remember him that on that day they would enter paradise together (Luke 23:42). The question is, what did Jesus mean, and what could this man who hung on a cross beside our Lord understand? In other words, Jesus had to have told him something he understood, otherwise Jesus’ words make no sense. First of all, Jesus cannot have referred to heaven, because heaven as the reward of the righteous has no place in the worldview of a first century Jew. The Jewish hope was to be found in the bosom of Abraham (cf. Luke 16:22:23). However, there was no consciousness in the grave, according to the scriptures (cf. Psalm 6:5; 115:17; 146:4; Ecclesiastes 9:10), and every Jew knew this. They looked forward to a resurrection. The grave was separated into two camps, those who would rise again, and those who would not. Those who would rise again were in paradise or Abraham’s bosom. When Jesus promised this man he would be with him in paradise, Jesus promised the man he would be in the resurrection.
Luke doesn’t mention that both criminals mocked Jesus, but Matthew does (Matthew 27:44), so, one wonders what changed the second criminal’s mind. What happened to cause him to repent and admit to his crimes and rebuke the first criminal. Of course, such a thing cannot be known for certain, but an ancient Jewish tradition does place the criminal’s repentance in a logical context:
When he is about ten cubits away from the place of stoning, they say to him “Confess”, for such is the practice of all who are executed, that they [first] confess, for he who confesses has a portion in the world to come. Even so we find in the case of Achan, that Joshua said to him, “My son, give, I pray thee, glory to the Lord, the God of Israel, and make confession unto him.” and Achan answered Joshua and said, “of a truth, I have sinned against the Lord the God of Israel, and thus and thus have I done.” And whence do we know that his confessions made atonement for him? — From the words, “And Joshua said: ‘Why hast thou troubled us? The Lord shall trouble thee this day.’” I.E. This day art thou to be troubled, but thou shalt not be troubled in the next world. [Babylonian Talmud: Mishna. Sanhedrin 43b]
This excerpt tells us what would have occurred, if the Jewish authorities were executing Jesus and the other two criminals. However, since the Romans were executing them, the Jewish authorities wouldn’t have an opportunity to perform this rite, until Jesus and the two with him were already hanging on the cross. Therefore, it can be assumed, if the Talmudic record is true (and there is no good reason to disbelieve it), then the repentance of the second malefactor is understood in the light of the Jewish authorities offering him an opportunity to set things right between him and God. Nevertheless, having repented, it seems he must have had some contact with Jesus before his arrest, and he must have been impressed by what he had witnessed at that time. Moreover, having been scheduled to die with Barabbas, it is very likely that he had witnessed the event of the Jewish authorities’ choice of Barabbas over Jesus, whom Pilate had found innocent of the crimes levied against him. Thus, he claimed that Jesus had done nothing wrong.