1. Jesus was delivered legally into his hands,
2. Jesus had assured him that this was all Heaven's plan, even Pilate's own part in it,
3. the crowd wanted him killed,
4. and Pilate was known for his ruthlessness...
... what was the dilemma? I can see why he wouldn't set Jesus free, but why would he hesitate to have him killed?
“...why would he hesitate to have him killed?”
Probably because of speculation about the very thing you are unwilling to consider, despite the many attempts by people here to show you.
1Cor 2:14 But the natural man receiveth not the things of the Spirit of God: for they are foolishness unto him: neither can he know them, because they are spiritually discerned.
Pilate’s own wife had warned Pilate not to deal with this man having been troubled in her dreams...His own gut told him something was amiss. The Romans were known for what was called a “Strong sense of Roman fair play”. He understood authority. Jesus would simply just love Pilate with a love that controls that universe...that is what Pilate was confronted with. Unadulturated love...and Pilate’s own response suggests he was being strongly influenced by it. Jesus from the cross forgave all those who put him up there...that would have included Pilate too. Could Pilate have forgiven himself? Who could say...Christ had already forgiven him!
No... not at first...not until the Jewish leadership sent their boys into the crowd to swing them their way....that's why it's wise to ‘focus on the leadership’ of both Rome and the Jewish leaders with the demand for Jesus’s death.....the crowd was simply manipulated like today. And of course Pilot was going to give them what they wanted.
...Pilate, knowing it was out of ‘self-interest’ that the chief priests had handed Jesus over to him........’the ‘chief priests’ stirred up the crowd to have Pilate release Barabbas instead......Wanting to satisfy ‘the crowd’..... Pilate released Barabbas to them. (Mark 15)
Pilot was aware the Jewish people were moved by their Leadership more than anything else....and that because the Leadership would have been ca-put for the following Jesus had already attained.