Josephus' use of the word "lestes" is noteworthy. He doesn't use the term to describe simple or common robbers or thieves. He uses it in connection with political activity and resistance, namely, of the zealots and sicarii (cf: War 2.254-270). Zealots and Sicarii were not engaged in simple piracy or banditry, though those things may have certainly been involved, but they were engaging in political struggle to expel the Romans and their partisans.
Additionally, this term is used in the New Testament to describe the two crucified with Jesus (Mk 15:27, Mat 27:38-44) and Barabbas (Jn 18:40) who we are told was arrested during a certain "insurrection" or "sediition" (Mk15:7, Lk 23:19.25) And no Roman law prescribed the death penalty for common robbery. Crucifixion itself was reserved for enemies of the state or rebels.
Jesus also uses the term to describe how he believed the local authorities thought of him (Mt 26:55, Mk 14:48, Lk 22:52)
Prisoners did not await justice for extended periods of time; there was no prison network as we may think. Trials and sentencing were swift, especially for sedition. The Romans also retained the authority to sentence people to death. Thus, the two crucified with Jesus and Barabbas would have likely been arrested in close proximity in time to when Jesus himself was arrested, and likely at a time when Pilate was in town, otherwise they would have been sent to Pilate when he was in Caesarea.
Pilate would travel to Jerusalem around important days, such as Passover (eg Ant 17.222, War 2.301)
So the two criminals and Barabbas would have likely been arrested at a time near to the time of their trial, sentencing, and execution and when Pilate was in town. The most likely candidate seems to be that they were arrested for something that occurred during the same Passover week when Jesus was arrested.
If, as we might popularly imagine, that it was simply Jesus walking around yelling at people and tumping over a few tables, it would have been somewhat easy for the locals so stop him, and not to mention hardly scary for local authorities. One person creating a scene would have been easy for the temple police to deal with.
To prevent business, and worry the authorities enough, Jesus would have had sufficient help to cover the large area and sufficient sway with a sufficient number of people so that that the authorities couldn't arrest him and that he could actually achieved his goal.
Thus, the "temple cleansing" may be better imagined as a riotous mob rather than imagining it as an Easter play. In that case, the authorities would have been extremely worried and normal business would likely have stopped.
Such a scene in the days leading up to Passover would have been very worrying to both the local authorities and the Romans and could very well have been interpreted by them as seditious and the people involved as "lestes."
So, it's reasonable to conclude that the two criminals, Barabbas, and Jesus were all arrested due to the same occurrence, namely, the "temple cleansing."
Though that's not to say that they were all doing the exact same thing (eg, Barabbas murdered someone, Jesus didn't)
As an alternate possible event, we have Jesus' arrest at the Garden of Gethsemane. Rather than imagining it as a passive event where the authorities show up and simply arrest Jesus, this event to may have been rowdy and more difficult
After all, the disciples were armed to some extent (Lk 22:36-38) and at least one is recorded as putting up a fight (Lk 22:49-50). So perhaps there was more resistance than thought?
Though without much further, the "temple cleansing" seems the likely event.
If the "temple cleansing" was something as described here, then the "triumphal entry" may have similarly resembled a passionate mob rather than people laying down a few coats and calmly waving palm branches.
This is suggested in the NT itself (Mt 21:10, Lk19:37) and seems to cause enough of a stir to worry some in the crowd (Lk 19:39). Perhaps their worry was that the crowd was out of hand?....
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