This death was a humiliating death. Both the Roman and Jewish cultures were shame and honor cultures. Crucifixion was intended to discourage those thinking about a life of crime or political rebellion. Not only would the criminal be killed, but his family would endure lasting shame.
Yet in spite of being at a low point in life, one of the criminals finds it in himself to ridicule Jesus.
This would be funny if it were not so sad. Ridicule is done by people who feel they are above people they consider beneath them. He thinks Jesus is a fool who has been going around claiming to be the Messiah.
Actually, Jesus never makes this claim in a direct way, but that is what people have been saying about him. So this criminal uses some of his final time on Earth to mock Jesus.
CS Lewis in his book “Mere Christianity” describes the biggest sin of all when he writes:
The vice I am talking of is Pride or Self-Conceit: and the virtue opposite to it, in Christian morals, is called Humility… According to Christian teachers, the essential vice, the utmost evil, is Pride. Unchastity, anger, greed, drunkenness, and all that, are mere flea bites in comparison: it was through Pride that the devil became the devil: Pride leads to every other vice: it is the complete anti-God state of mind.
But the other criminal has a very different attitude. He admits he is getting what he deserves. He rebukes the other man, asking him if he doesn’t fear God. This implies that this criminal does. He not only fears God, but he is also able to look at his own life and accept his punishment as just.
He then turns to Jesus and asks for mercy. He identifies Jesus as an innocent victim and requests to be remembered when Jesus comes into His kingdom. This criminal is able to look in four directions. In the midst of terrible pain at the end of his life, he examines himself. He looks to God. He speaks to the other criminal and then he looks to Jesus and asks for mercy: “Remember me when you come into your kingdom.”
Jesus’ reply should give us all hope. It is a reply that promises mercy. Notice that this promise is
spoken to one thief and not the other: “You will be with me in paradise.”
Jesus accepts the man’s faith, his trust that He has the power to save him, not from the cross, but from eternal death.