The Pilate we see in the Gospels is a brutally pragmatic, self-interested political beast.
I find nothing in the text to indicate that he was doing anything 'sympathetic' or atypical insofar as the Jews were concerned or Rome's occupation.
A 'sympathetic' Pilate would not have scourged Jesus - and then Crucified Him all the same.
Well, that's not sympathetic according to modern sensibilities. But by the standards of the age? Gibbon reports that during periods when the Roman empire outlawed Christianity, it was a common practice for Roman magistrates to arrest people who'd been denounced as Christians, torture them until they agreed
not to confess to being Christian, and then let them go.
Pilate was simply juggling all the various factors and factions.
Release Barabbas?
Sure, then have him followed and quietly kidnapped and executed.
Crucify Jesus and release Barabbas? Not bloody likely.
The first thing you need to know is that the New Testament was written in Greek, and Greeks stuck "s" on the ends of foreign men's names to make them sound masculine to Greek ears; this is part of what happened to Yeshua on its way to becoming Jesus.
The second thing you need to know is that, just like in thousands of other languages, in Aramaic people were often referred to as "the son of so-and-so", and it has a prefix that means "the son of", equivalent to "Mac" in Scots Gaelic and "Ben" in Hebrew. In Aramaic the prefix that means "the son of" is "Bar".
So there was nobody literally named "Barabbas"; what there was was a guy people called "Bar Abba".
The third thing you need to know is that "Abba" is the Aramaic word for "father".
Note, the name Barabbas is a Hellenization of the Aramaic Bar Abba (בר אבא), literally "Son of the Father".
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Source)
So whoever wrote that story into the New Testament had evidently heard, probably at second or third hand, that when Pilate had Jesus in custody there was a crowd of local Jews making a fuss, and Pilate asked them what they wanted from him, and the crowd said "We want you to release the Son of the Father".