This idea came to me recently after hearing a sermon that was taught through an interpretation of the story behind the robbers on the cross, in the gospel of Luke chapter 23. I know that asking if Judas is the robber seems out of left field, but I have some passages and ideas that can support this theory.
Let's get your mind going. How many people do you meet that has the name Judas? People all around know about the story of how Judas betrayed Jesus, even non-believers. We like to point the finger to others and say, "At least I'm not as bad as that guy." How many of us look at Judas this way? The theory of Judas as the robber on the cross may change the way you look at Judas.
So to start off, I know those of you who know the scriptures are already thinking about how the Bible says Judas hung himself. How could he possibly be the rebel/robber on the cross if it says he hung himself? Let's take a look at those passages. In Matthew 27:3-10, it says that Judas was filled with remorse and returned the 30 pieces of silver to the chief priests and elders. They don't accept his money back, so he throws it in the temple. "Then he went away and hanged himself." (v5) After that, the priests and elders decided that since this money is "blood money" they can't use it for the temple. So they go buy a field to make a burial place for foreigners.
Now, lets look at the second passage about the death of Judas. It's not mentioned in the other gospels, although in chapter 1 in the book of Acts it mentions as kind of a side note about Judas's death in verses 18-19. It says that Judas bought the field with the 30 pieces of silver where he fell headlong, and all his intestines spilled out. Question: If you are hanging by your neck and fall, what hits the ground first, your head or your feet? It says he fell headlong/ headfirst, not feet first. So to me this does not imply that he hung himself.
Woah! Wait a minute. Did the Bible just dispute itself? This question could easily start a huge controversy, because it puts into question those 66 books in which some of us put our faith in, and derive all of our beliefs from. So is the Bible 100% fact? Maybe not. Although I believe there is complete truth in the Bible. I believe the Bible is a compilation of books written over thousands of years about the love of God for man, how man turns from God, and how God still redeems man through His son Jesus. That's how I live with the truth of the Bible.
Moving on, here you have two different accounts on how Judas dies. For whatever reason, one of them has to be false. Here's where my theory comes into play.
John 12:6 says that Judas was the keeper of the money bag and that he would help himself to what was put into it. This makes Judas a thief, because he would steal from the bag of money that was meant for all the disciples. That being said, if you will allow me the liberty to interpret Judas's story it will all come together.
What if, before Judas met Jesus, he was a greedy robber. He would find various ways to rob people because he was greedy with his money. Knowing this, Jesus makes him the treasurer over the disciples to give him a chance to understand that money isn't everything. Having nothing to lose, Judas becomes a follower of Jesus. Judas would hear Jesus teach, watch Him become popular, and begins to believe that Jesus will become the great political King of the Jews. Judas begins to think if Jesus becomes king, and he is the treasurer, that would make him very rich for when that time comes. As time goes on, Judas begins to think that Jesus is going too slow with starting His kingdom so he decides to push Him to speed things up by giving Him over to the authorities. Judas might be thinking that his betrayal could be the jumpstart to Jesus's reign, because it would force Jesus to take action. In contrast Jesus doesn't resist or fight back. Judas is confused. Jesus gets put on trial in the temple, is mocked, and beaten. Seeing this, Judas becomes filled with remorse. Things didn't go as planned. He realizes that maybe Jesus was talking about a different kind of kingdom the whole time. What had he done? Did he just turn in the one true King to be sentenced to death? He can't handle it anymore and turns himself in to the priests. He admits his sin to them (Matt 27:4) and leaves. He then gets seized by the officials outside the temple, since he pledged guilty to his crime. He was then taken to cross to be hung. Therefore, going away and hanging himself (Matt 27:5), since it was him that pleaded guilty. Judas would already be hanging when Jesus is put on the cross next to him. The people begin to mock Jesus, along with the other criminal hanging next to them. Again Judas can't take it anymore. He has to show Jesus he finally believes. He then turns to the other criminal, "Don't you fear God since you are under the same sentence? We are punished justly, for we are getting what our deeds deserve. But this Man has done nothing wrong." Then he said, "Jesus, remember me when you come into Your kingdom and Your kingly power." Judas, the one who used to call Jesus teacher, now understands His real purpose and calls Him King. Jesus says to him, "Truly I tell you, today you will be with me in paradise."
I would say that the gospels wouldn't mention this theory even if it was Judas that was on the cross next to Jesus. I'd imagine that all of the disciples still had bitterness towards Judas when they wrote the gospels, and wanted to end his story with, "he got what he deserved". It says at least 12 times throughout the gospels that Judas was either a traitor, or the one who betrayed Jesus. Almost every mention of Judas is either negative, or is about his betrayal of Jesus. So I'd say it's safe to say they were still bitter about what he did.
Aside from this theory, I doubt anyone believes Judas will be in heaven unless Judas was that robber on the cross. It would be so typical of Jesus to forgive him if it were. That's where, "The first will be last, and the last will be first" comes into play so well (Matt 19:30; 20:8; 20:16; Mark 9:35; 10:31; Luke 13:30). As far as we know, that robber was the first to enter the kingdom of heaven. Jesus was so loving that He would have had the ability to show love to the very one who betrayed Him, while He was in agony, dying on the cross. That is the power of the gospel.
All this is just a theory, and I am leaving it up to you. This may or may not have happened, and most likely not. Either way, I believe if Judas was on the cross next to Jesus, that Jesus would have had the power to forgive even him. So may we go with that same power of love in mind to be able to love those who betray us, even when we are at our lowest point!