Let’s consider where Judas went wrong. I see two things - one that led to his betrayal of Jesus, and another thing that is far worse. 

Then one of the Twelve—the one called Judas Iscariot—went to the chief priests and asked, “What are you willing to give me if I deliver him over to you?” So they counted out for him thirty pieces of silver. From then on Judas watched for an opportunity to hand him over.” - Matthew‬ ‭26‬:‭14‬-‭16‬. 

One theory is that Judas wasn't trying to harm Jesus, but was trying to move Jesus to action. If he forced a showdown between the high priest and Jesus, then Jesus would finally flex his Messiah muscles and start the revolution - the revolution that Judas and other zealots were waiting for.

If this theory is true - and I think there's good reason to believe it is - then it makes me sympathize with Judas even more. He believed it was God's will to overthrow the current system of corruption. He believed Jesus stood for the kingdom of God (he did, of course). But he could not trust Jesus' plan. He believed he had to take matters into his own hands. He believed he had to move things along. 

First wrong turn: Judas operated out of the flesh, out of his own sense of wisdom and strength and ingenuity. He thought he knew what needed to happen, and that he was the one to “help God out.”

I can understand that. I have had multiple moments over the course of my life (maybe even multiple moments over the course of each day) where I think something is God’s will and that I need to “make it happen.” 

Take a moment and reflect on where you may be trying to “help God out;” where you may be trying to take matters into your own hands; where you may be trying to make happen what you believe is God's will through your own manipulative efforts. 

Is it in your marriage? With your kids? Something at your job?

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Let’s continue in Matthew 26:

When evening came, Jesus was reclining at the table with the Twelve. And while they were eating, he said, “Truly I tell you, one of you will betray me.” 

They were very sad and began to say to him one after the other, “Surely you don’t mean me, Lord?” Jesus replied, “The one who has dipped his hand into the bowl with me will betray me. The Son of Man will go just as it is written about him. But woe to that man who betrays the Son of Man! It would be better for him if he had not been born.” 

Then Judas, the one who would betray him, said, “Surely you don’t mean me, Rabbi?” Jesus answered, “You have said so.” - ‭‭Matthew‬ ‭26‬:‭20‬-‭25‬ ‭NIV‬‬

I don’t know if Jesus is saying that Judas betraying him was so bad that it would be better if he had not been born… OR if Jesus was speaking about the self-condemnation that was coming Judas’ way just a few hours later when Jesus was handed over to Pilate. 

When Judas, who had betrayed him, saw that Jesus was condemned, he was seized with remorse and returned the thirty pieces of silver to the chief priests and the elders. “I have sinned,” he said, “for I have betrayed innocent blood.”

 “What is that to us?” they replied. “That’s your responsibility.” So Judas threw the money into the temple and left. Then he went away and hanged himself. - ‭‭Matthew‬ ‭27‬:‭3‬-‭5 NIV‬‬

His sin led to remorse, then to a deadly kind of self condemnation and ultimately his destruction. He didn't get to experience the freedom that Jesus was purchasing on the cross. 

He gave up before he could see God turn his sin into glory.

Here's an excerpt from a commentary I've been reading:

"Remorse and repentance both begin with looking at something you’ve done and realizing it was wrong. But the first goes down the hill of anger, recrimination, self-hatred and ultimately self-destruction, the way that leads to death. The second goes down the route Peter took, of tears, shame, and a way back to life." Excerpt from: "Matthew for Everyone, Part 2: Chapters 16-28" by N. T. Wright. 

An Even Worse Wrong Turn

What made it better for Judas to have never been born was not being seduced by Satan… But in thinking he could never come back from it. He believed there could be no grace.

When my kids misbehave, it’s frustrating. But what really troubles me is their belief that they must avoid us out of their shame - as if our love for them has changed.

Our sins certainly dishonor Jesus. But what is most dangerous is to not believe He can and will forgive us. 

Where do you need to move from unhealthy remorse into godly, life-giving, soul replenishing repentance? Where do you need to stop wallowing in self-condemnation and run into the grace that Jesus purchased for you?