In the very early hours of Thursday morning of Passion week Jesus was interrogated by Annas and then Caiaphas, and then at the break of day condemned to death by the Sanhedrin for truthfully confessing Himself to be who He was—the Christ, though not in the sense they were expecting. Having now been bound and delivered up to Pilate for execution, Matthew also reports the mistaken expectations of Judas, who having never truly repented of his love for worldly gain could not imagine that someone with Jesus’ power would allow himself to be put to death. Assuming Jesus would do something to save Himself, Judas likely supposed that the confrontation he had arranged with the Jewish leaders would result in the sort of kingdom they were all expecting. Considering how much higher God’s ways are than our own, and how fallible our own expectations can be, should we ever suppose that we are able to “help God out” by taking matters into our own hands in order to fulfill our own expectations of what we suppose His kingdom to be, or how we imagine He will respond? Cf. Ecc 5:1-2. If we are to be led by His Spirit and follow His leading, what must our prayer always be? See Mat 26:39,42,44.
What does Matthew say Judas felt when he saw that in fact Jesus was condemned contrary to his expectations? Is remorse the same as godly sorrow and true repentance? Notice that the Greek word used (μεταμέλομαι) is not the same word used elsewhere for true repentance (μετάνοια), but means merely that he changed his mind and regretted what he had done. See 1Sa 15:35, Mat 21:29,32, 2Co 7:8, Heb 7:21 and observe that remorse or regret is only the feeling of sorrow that one experiences for some happening, but not the response itself that the feeling provokes. Such remorse may be a godly sorrow that is so moved with regret for what happened that it has no regrets turning away from it back to God in true repentance. But it may also be a worldly sorrow that while remorseful for the consequences of what happened, from fear of the ignominy of owning up to it regrets even more the thought of turning to the Lord in sincere repentance to accept responsibility and do what is possible to right the wrong, so that it leads to death; see 2Co 7:8-10; cf. Pro 14:12. For what reasons would Peter, and Paul, have had the same fear? See Mat 26:33,40,51,69-75, 1Ti 1:12-15. How do their examples illustrate that we need not fear humbling ourselves to acknowledge even our worst failures, knowing that God is able even in this life to raise us up from our sinful despair if only we will turn to Him? In addition to Paul’s confession as the foremost of sinners, recall that the most unglamorous picture of Peter in all the gospels is painted by Mark, whose main source of information was Peter himself. And yet, because of their failures, and the humility to turn to God and so freely confess both their sins and God’s grace to forgive and receive them back in spite of their sin, God was able to use them mightily to save multitudes.
What two things does Matthew record that Judas’ remorse prompted him to do? See Mat 27:3-4a. What does this indicate about his desire to try to undo the results of his deed? While such gives the appearance of repentance, was it in fact so easy at that point to correct his mistake by simply returning the money and confessing his sin? How is that like so many today who seek an easy way out of the difficult circumstances their sins have put them in, but are not truly committed—as Peter and Paul were—to demonstrate by a renewed life the sincerity of their repentance? In what way did the lives and ministries of Peter and Paul demonstrate their godly sorrow unto true repentance in contrast to the worldly sorrow unto death of Judas? What does Judas’ example teach us about confession of sin and returning ill-gotten gain not necessarily being a clear indicator of true repentance?
Rather than confessing his sin and trying to make things right through the chief priests, to Whom ought Judas to have confessed his sin and tried to make things right? Although Judas may have imagined he was setting a trap for the corrupt religious leaders, in what way was he ensnared by his sins so that he ended up being caught in their own trap and used to accomplish their purposes? See Mat 27:4b. What anguish from his foolish sin for which Jesus was already suffering would have made it extremely difficult for Judas to face Him, even if he could at that point? And because he could not at that point, what personal sacrifice would he have had to make to try to undo his deed before the Roman governor? And yet, because of his sinful love for the world, was it within him to lay down his life for Jesus at that point? What does this teach us about the inescapable snare in which the twisted lies of sin are able to catch sinners and hold them fast? Should we suppose that we are able to escape such snares somehow better than one of Jesus’ own apostles who personally walked with Him for three years if our heart is divided and we are not committed to understanding and obeying His word?
 “See here how Judas repented: not like Peter, who repented, believed, and was pardoned: no, he repented, despaired, and was ruined.” Matthew Henry.
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- What is the relationship between Jesus’ sacrifice and our redemption, forgiveness and receiving an inheritance per the terms of the covenant / will that was effected by His death?
- From what, and to what, are we saved? Is it Jesus’ death alone that saves us? What part does His resurrection have in our salvation?
- Does the justice of God demand the satisfaction of blood before He will forgive, similar to what pagans throughout history have believed?
- What was the purpose of the Old Testament sacrifices?
- Does blood alone atone for sin?
- How does Christ’s death render powerless the devil?
- To whom was Christ’s life given as a ransom? From what are we ransomed?
- Why did Jesus not only die, but suffer and die? If all that was necessary was His shed blood, why didn’t God sovereignly ordain a more merciful death for His own dear Son?
- What is the relationship between a will or testament, and a covenant? What was willed to Jesus as an inheritance from His Father, and what was willed to us through the new testament in His blood?