Many teachers wonder how the thief could be a disciple of John or even a disciple taught by Christ, you have to consider the thief in the context of insurrection. Those who had been arrested were mostly insurrectionists. Though tradition calls them thieves the Greek text does not, it refers to them as evil workers or subversives. The word is kakoergoi which could be a thief but could also be any criminal, including one who stirs up insurrection. That means they fought against the occupation of Rome and could be the most religious of their society. Barabbas who was released was asked for by the Jews, it makes sense they would ask for a murderer if he was an insurrectionist supporting the Jewish cause of freedom. Instead of seeing him as a murderer they viewed him as a hero. They supported physical resistance to Rome which was different from Jesus.
Just realize the Greek doesn't call them common thieves specifically. The word is leptes vs kleptes, which signifies violence. As one supporting insurrection. It is violent robbery. It isn't stealing bread from a baker's window.
The thieves/evil workers were likely part of the gang of Barabbas and helped with insurrection. They weren't common thieves but those who became thieves in supporting the cause. Many troops in war might take food or animals from farmers and such along the roads and hills of battle. Many soldiers get very hungry and are forced to get food where they can. Taking spoils after skirmishes might also be considered thievery by the Roman government. I see them as beating up and robbing Roman citizens, officials, and even soldiers. They could not be convicted of murder.
Since Barabbas and others in prison were there for insurrection they may have been thieves in a legal sense, but were likely very religious Jews who awaited the messiah.
Mark 15:7
And there was [one] named Barabbas, [which lay] bound with them that had made insurrection with him, who had committed murder in the insurrection.
Notice those bound made insurrection with Barabbas. The thieves were likely part of a group fighting to overthrow the Romans. They weren't common thieves but most likely religious freedom fighters. This took place in the city. Insurrection would be a crucifiable offense where common thieves would not be.
The thief isn't a simple thief but likely religious. He was likely taught by John the Baptist and possibly Jesus because of his knowledge. Both taught the kingdom was at hand and over zealous men would physically fight, though neither John or Jesus called for such.
Mark 1:3
The voice of one crying in the wilderness, Prepare ye the way of the Lord, make his paths straight.
Preparing the way of the Lord could be seen by some rabbis to include insurrection against Rome.
Mark 1:15
And saying, The time is fulfilled, and the kingdom of God is at hand: repent ye, and believe the gospel.
Satan could use insurrection to generally turn Rome against any insurrectionists, even those looking for a spiritual insurrection such as the Gospel. They wanted no ruler but Caesar.
just realize the thief was likely very religious, willing to die for freedom for his people.