Judas regretted what he had done, or he changed his mind, or he repented (Matthew 27:3). The exact wording will depend on your translation. The word that is used is a synonym of the usual word for repent in the New Testament, and it is difficult to distinguish the two synonyms. The word used of Judas seems to have a range of meaning from the feelings of regret to the change of mind, which is what repentance is.*
For the reader of Matthew, the word is first encountered in the parable of two sons who are told to go work in the vineyard (Matthew 21:28-32). The first son says he won’t go, but later changed his mind and went (verse 29). Here is an example of genuine repentance.
As we look at the case of Judas, there are some positive signs of repentance as well. Judas returned the thirty pieces of silver. As Jack P. Lewis in his commentary on Matthew noted it was a “paltry sum” in comparison to what Judas traded, but it still amounted to about four months’ wages for a laborer. It was no small amount to part with once it was already in your pocket. Judas also confessed to the chief priests and elders, “I have sinned by betraying innocent blood.”
So what went wrong? Judas’ regret didn’t lead him back to God. Instead, he took his own life. He took vengeance out on himself instead of leaving it for God, which by the way, also means leaving room for grace to intervene. The Jesus who forgave Peter, the denier, and Paul, the persecutor, would seem to have sufficient grace for a Judas, the betrayer. Judas ended his life before Jesus’ resurrection —before the full power of the good news was known.
Judas seems to be the poster child for Paul’s teaching on grief and repentance.
For godly grief produces a repentance that leads to salvation without regret, whereas worldly grief produces death. 2 Corinthians 7:10, ESV
What we do with grief and regret is important? Turn it in the wrong direction, and it leads to death. Turn it in the right direction, and it leads to forgiveness and salvation. Regret is not enough. Grief is not enough. The feelings of regret and the inward changes must lead us in God’s direction to God’s solution.
*The Greek word is metamelomai. The usual verb for repent in the New Testament is metanoeo.