It is very early in the morning on Thursday of Passion Week and Jesus has already faced a gauntlet of three inquisitions or trials before the Jews and is about to face the same before the Gentiles; what does this remind us about the sound rejection of God’s King and His kingdom by the kingdoms of this world, both Jew and Gentile? See Deut 17:6, 19:15, Mat 18:16, 2Co 13:1, 1Ti 5:19. Having been judged guilty informally by Annas even before His arrest, and then by Caiaphas and his cronies during the night with the exact charges they would present to have Him put to death, a guilty verdict was then quickly delivered at the break of day by the Sanhedrin so that Jesus might be put to death that day to prevent a potential uprising by acting before His followers had time to riot for His release; cf. Mat 27:24. Now, having bound and delivered Him up to Pilate for execution, what does Matthew interject in His narrative that also happened at that time? See Mat 27:3-5. How is it that Judas “saw that He had been condemned”? What does this statement at this point in Matthew’s narrative indicate about Judas being at the very least near to Jesus’ trial before the Sanhedrin so as to see its outcome, if not actually present at it? Why is it possible, as the one who betrayed Jesus, that Judas would have been at the formal trial, or at least kept in the wings by the chief priests, though not necessarily at the earlier inquisitions?
What was it that Judas saw that caused him to feel remorse? See Mat 27:3. What does this indicate about his expectation that Jesus would not be condemned? Because he was clearly aware of the religious leaders’ desire to put Jesus to death, both from their own willingness to pay him to deliver Him up to them as well as Jesus’ own statements (Mat 16:21, 17:22-23, 20:17-19, 26:2, Joh 11:8,16), what can we surmise that he expected to happen? I.e., although he didn’t know the details for how it would happen, what did he likely suppose was going to happen, that he was deceived to believe he had orchestrated in order to help usher in the sort of kingdom they were all expecting, and that was egged on by his perturbation over Mary’s “waste” of the precious anointing oil (Mat 26:6-9, Joh 12:1-6)? Cf. Mar 10:35-37, Act 1:6.
Consider that Judas was chosen as an apostle of the Lord and walked with Him for a significant amount of time, hearing Him teach and seeing His miracles so that he was more intimately acquainted with Jesus than most, and was even himself a recipient of His divine power to cast out unclean spirits and heal every kind of sickness and disease (Mat 10:1); should we be surprised that Judas, whose heart was still set on worldly gain, could not imagine that anyone like that would actually allow himself to be bound and delivered up for execution? What does this remind us about God’s ways being much higher than our ways, so that it is never prudent, especially on the basis of our worldly perceptions, to make such a bold bet? Cf. Is 55:8-9, Mat 4:5-7. What does it also remind us about the great danger of a divided heart that seeks both worldly gain and to serve God? Cf. Mat 6:24. In what ways do we see both pride and greed at work in Judas’ deception? What does his example teach us about the great danger of these sins, and the importance of guarding against them? In what way does Judas’ understanding of real life as the avoidance of death contrast with Jesus’ understanding of real life as fellowship with the Father through obedience to His will, even unto death? Cf. Joh 17:3. In what way does the consequence of his misunderstanding of what is real life also illustrate the consequences of misunderstanding the true gospel, that provides not just forgiveness of sins, but also deliverance from its power through death?
After such a bold bet that Jesus would manifest His power to establish the sort of worldly kingdom he was expecting, what sinking feeling would Judas have experienced as Jesus did not respond to the situation as he had imagined, and his expectations were not fulfilled? How is that similar to the feeling every sinner experiences as he comes to realize its deception? Cf. Gen 3:7. How would the Jews in 70 a.d. have experienced the same sinking feeling as their expectations were likewise not met that the Messiah would appear to save them from the Romans as Jerusalem was surrounded? What does this remind us about the great danger of misplacing our expectations according to our fleshly desires, and the importance of seeking to understand the truth and aligning our expectations according to it? Is it possible that many American Christians today could also have misplaced expectations, and are perhaps even beginning to experience the same sinking feeling that the Jesus they have hoped would rapture them to heaven has not yet appeared, even as the armies of the world have surrounded and are now closing in on them?