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Why one of the two thieves hanged with Jesus chose to go to Hell
Leviticus 18:21-24 KJV And thou shalt not let any of thy seed pass through the fire to Molech, neither shalt thou profane the name of thy God: I am the LORD. (22) Thou shalt not lie with mankind, as with womankind: it is abomination. (23) Neither shalt thou lie with any beast to defile thyself therewith: neither shall any woman stand before a beast to lie down thereto: it is confusion. (24) Defile not ye yourselves in any of these things: for in all these the nations are defiled which I cast out before you
In that era at the part of the world it would've been well known to people that any violation would prohibit a person from being welcomed by God into paradise.
Matthew 27:38-44 MKJV Then two thieves were crucified with Him, one off the right, one off the left. (39) And those who passed by blasphemed Him, shaking their heads, (40) and saying, You destroying the temple and building it in three days, save yourself. If you are the Son of God, come down from the cross. (41) And in the same way also the chief priests mocked, with the scribes and elders, saying, (42) He saved others, but he cannot save himself. If he is the King of Israel, let him now come down from the cross, and we will believe him. (43) He trusted in God, let Him deliver Him now, if He will have Him. (For He said, I am the Son of God.) (44) And also the thieves who were crucified with Him reviled Him, saying the same.
The chief priests mocked him saying that they doubt that God would have Jesus, if that was the general consensus amongst Elders, scribes, and chief priests there could be no doubt about homosexuals being unwelcome by God.
Luke 23:39-43 MKJV And one of the hanged criminals blasphemed Him, saying, If you are Christ, save Yourself and us. (40) But answering, the other rebuked him, saying, Do you not fear God, since you are in the same condemnation. (41) And we indeed justly so, for we receive the due reward of our deeds, but this Man has done nothing amiss. (42) And he said to Jesus, Lord, remember me when You come into Your kingdom. (43) And Jesus said to him, Truly I say to you, Today you shall be with Me in Paradise.
One of the hanged criminals asked to be free of his punishment, not a place in Paradise with Jesus. It is here where the criminal gives away that he has no doubt that he is beyond saving. He continues to blaspheme Jesus instead of showing fear of God.
Mark 15:27-32 MKJV And with Him they crucified two thieves, the one off the right, and one off the left. (28) And the Scripture was fulfilled which said, "And he was numbered with the lawless." (29) And those who passed by blasphemed Him, wagging their heads and saying, Aha! You razing the temple and building it in three days, (30) save yourself and come down from the cross! (31) And also the chief priests mocking, with the scribes, said to one another, He saved others but he cannot save himself. (32) Let Christ the King of Israel now come down from the cross, so that we may see and believe. And they who were crucified with Him insulted Him.
Here the scribes testify to Jesus saving others, but only one of the hanged thieves shows fear of God. It is here where the thief who goes to hell by choice shows that he had already accepted that he would not be welcomed by God.
This is a private interpretation and is inspired by the Three Crosses placed alongside the highway near Charlotte Michigan, during the late 80's-early90's, by a person who made a pilgrimage to Jerusalem, while never declaring a reason what the putting up the display meant.