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Although Judas was remorseful for betraying Jesus, he wasn't repentant. Had he repented, he would not have hung himself. Rather, he would have used the remainder of his life to bear fruit for the glory of God. Keep in mind that it really wasn't Judas alone who was responsible for Jesus' death; it was you and me also. Our sins killed Him. But unlike Judas, we repented and now live for God.
The chief priests and elders wouldn't place Judas' returned money in the Temple treasury because it was unlawful to accept donations that were gained by doing what they had just paid Judas to do! What hypocrisy! More amazingly, after they'd condemned an innocent man---God in the flesh---they wanted to do the right thing before God with the returned betrayal money! So they purchased a potter's field as a place to bury foreigners. In doing so, they unwittingly helped prove that Jesus was indeed the Messiah by fulfilling Jeremiah's prophecy that the 30 pieces of silver used to betray the Messiah would be used to purchase a potter's field!
Cowardly Pilate thought he could extricate himself from having to condemn Jesus by offering the Jews a choice of whom he would release---Jesus or a known murderer and insurrectionist named Barabbas. Surely the people, when offered such a choice, would vote for the release of Jesus. To Pilate's horror, however, they shouted for Barabbas' release. I wonder how Barabbas felt as he walked free that day? What a picture of the purpose of Christ's coming in this one incident: Innocent Jesus was condemned, and because of it the guilty one was pardoned. Barabbas represents you and me.
According to John's Gospel, Pilate had Jesus whipped 39 times in hopes of saving Him from crucifixion. Surely after seeing him scourged the Jews would say He had suffered enough. A Roman scourging was sometimes enough to kill its victim, as sharp bone fragments were attached to the ends of the whip's lashes so that the scourging ripped the flesh from its victim. Even after seeing Jesus' lacerated back, however, the mob still demanded his crucifixion.
Had Jesus accepted the wine mingled with gall offered to Him on Golgotha, it would have relieved the pain of the nails ripping through His flesh considerably. He was willing, however, to suffer to the full extent, and He didn't want His senses to be dulled as He endured God's wrath. Amazing love! And how little did His mockers, who shouted, "He saved others; He cannot save Himself" (27:42), realize the accuracy of their words. If Jesus was going to save others, He couldn't save Himself.
Matthew's targeted Jewish readership would have recognized five direct Old Testament references in today's reading, four from Psalm 22 and one from Psalm 69. It had been prophesied that Jesus would be offered wine mixed with gall, that lots would be cast for His clothing, and that He would be mocked by the spectators. Jesus Himself directed the onlookers to His prophetic connection to Psalm 22 when He quoted its first verse: "My God, My God, why hast Thou forsaken Me?"
Immediately after Jesus died, the curtain in the temple that separated the holy place from the holy of holies was ripped in half from top to bottom. The significance is obvious. Jesus paved the way for every person to have access to God. Incidentally, the tearing of the temple curtain also proves that Jesus did not continue suffering in hell after His death in order to pay for our redemption there (as some teach). Our sins were paid for in full on the cross. Jesus cried out with His final breath, "It is finished!" (John 19:30), a phrase that can also be translated, "It has been paid in full!" Paul wrote, "He has now reconciled you in His fleshly body through death" (Col. 1:22).
I'm glad the chief priests and Pharisees decided to make Jesus' grave as secure as possible, because that makes Jesus' resurrection even more believable. The resurrection of Jesus is a well-attested historical fact, and anyone who examines the evidence will have to conclude that Jesus is indeed alive.