“Woe to that man who betrays the Son of Man! It would be better for him if he had not been born.” Mark 14:21

“If you are not born again, the day will come when you will wish you had never been born at all.” --Warren Wiersbe

Perhaps the place to begin is at the end of the story. It is now early Friday morning in Jerusalem — sometime between midnight and dawn — and the Jews are finished with Jesus. They have had their kangaroo court with their trumped-up charges and their false witnesses. Annas has had a round with Jesus and so has Caiaphas. Their verdict is clear — this man is a blasphemer who deserves to die. The assemblage of religious leaders set out to take Jesus before Pilate, the Roman governor. He is the only one who can order Jesus put to death.

There is movement, noise, and clatter as the group moves down the rocky hillside toward the Praetorium inside the ancient walled city. In the shadows one man, now forgotten, watches, his face strained, his eyes puffy, his head slightly bowed. It has been a long night, the longest of his life. How many hours have passed since that meal in the Upper Room? Six, maybe seven, who knows? After he left, he went straight to the chief priests to make the final arrangements. Then there was the short walk in the darkness across the Kidron Valley and up the wooded slope of the Mount of Olives. The whole thing had not lasted five minutes. Just a blur, a few words, a kiss, some angry comments by Peter and the others, then Jesus was arrested and taken away.
By Sunrise He Changed His Mind
In his hands Judas held the little bag that contained the 30 pieces of silver. He hadn’t even bothered to count it. No one noticed him now. It was like he was yesterday’s news. No one had any use for a traitor.

Through the long night he had waited, hanging around the edges of the crowd, listening for some word of how things were going. What exactly did he expect? No one knows for sure. But if at midnight he wanted to see Jesus die, by sunrise he had changed his mind.

Memories flooded his mind. Things Jesus had said, little jokes the apostles used to tell, stories Jesus had told over and over again. Little pictures painted themselves in the darkness—the smile on the face of Jairus’ daughter when Jesus raised her from the dead, the look on Peter’s face when he walked on the water and it actually held him up, the picture of those 12 baskets of food left over after Jesus fed the 5,000. He could see it all and hear it all and the memories were almost too much to bear.

Then the rumor spread that Jesus had been condemned to die. He shouldn’t have been surprised, but he was. For a moment, there was a commotion in the courtyard and Judas saw Jesus as he was being led away to Pilate. He didn’t see him clearly, just a glimpse of his face from a distance, but he knew it was him.

Overwhelmed. That’s the only word to use. Judas was overwhelmed with the thought that Jesus was going to die. In that moment it came to him in a blinding flash: He had made a great mistake, the greatest mistake of his life, so great a mistake that he must somehow find a way to make things right.

Too Late
With that thought filling his mind, he took the bag of money and tried to give it back. But the chief priests laughed at him. They had no more use for him or his money. They had what they wanted.

In desperation, Judas cried out, “I have sinned for I have betrayed innocent blood” (Matthew 27:4). Every word was true. He had done it; what he had done was the worst sin imaginable; he had betrayed the Lord Jesus who, though he was innocent, was about to pay with his blood for Judas’ crime.

With that, he threw the money back into the temple, the coins clinking and ringing as they hit the stone pavement. As Judas turned to go, the 30 pieces of silver stayed behind. Judas not only lost his Lord, he also lost his money. Very shortly he would lose his life.