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After numerous predictions that He would be delivered up to the Jewish leaders and handed over to the Romans to be crucified (Mat 16:21, 17:22-23, 20:18-19, 21:38, 26:2), at Jesus’ last Passover He has now dropped the spiritual bombshell upon His disciples that it would be one of them who would betray Him.  Their shocked astonishment and soul searching highlights not only the odious nature of such treachery, but also the sinfulness of sin that will lead one to betray their own ideals and not even be true to themselves.  The very nature of sin is deception, and so deceitful is its nature that it is as easy for us as it was for Peter, and the other disciples, and Judas, to discount our own capacity to fall away, or deny, or even betray what we know in our hearts to be true, in spite of our pledge to faithfulness.  Contrary to our sinful nature, our only hope for deliverance from the deceitful nature of sin is not to pledge ourselves to be better, but to unite ourselves with Christ through obedience to be deader.  This begins with the heart-felt contrition of repentance by grieving deeply for our sinful nature and humbly acknowledging our capacity to sin and inability to do anything apart from our relationship to God; cf. Joh 5:19,30, 12:49, 14:10, 15:1-5,10 and think: if Jesus had sought to speak or do things on His own initiative and not been in constant communion with the Father, would He not also have had the same capacity to sin as we?  To the extent that we do not now so grieve over our capacity to sin that it drives us to the cross and keeps us connected to the vine, we will grieve all the more for the outcome of those sins later.

See Mat 27:3-5; in light of Judas’ eventual remorse when he saw that Jesus was condemned, perhaps never intending to betray Him to death but rather orchestrating events he supposed would lead to the establishment of the kingdom they all were seeking, many throughout history have questioned if it is possible that he might in the end have been saved.  What do Jesus’ words in Mat 26:24 seem to indicate about this possibility?  When a woe is pronounced by God, is that a pronouncement of chastisement, or judgment?  Cf. Num 21:29, Isa 3:9-11, Zep 2:5, Rev 8:13, 18:10.  When Jesus earlier pronounced woe upon someone, was that ever a good thing?  Cf. Mat 11:21-24, 18:7-8, 23:13,14,15,16,23,25,27,29,33, 24:19.  Some might argue that yes, he would have woe, which he certainly did (Mat 27:3-5) but does that necessarily mean he could not have been saved?

What does it mean to be saved?  Is salvation just a nebulous hope that when we die we will go to heaven where we can fulfill our hearts’ desires without fear of consequences, and especially death?  Or is it deliverance from all of the darkness and deceit of the world, the flesh and the devil that fits us to inhabit a kingdom prepared for us from the foundation of the world wherein dwells all that is true and noble and right and pure and lovely and admirable and excellent and praiseworthy (Phil 4:8)?  Is it conceivable that one who ignobly betrayed the righteous Son of God, even if forgiven, could ever experience the peace and joy we associate with a heaven that exalts all that is honorable?  Might not that ignominy torment him even more in that place of noble truth?

What was different about the thief on the cross (Luk 23:39-43)?  Were his sins necessarily of the same nature as that of Judas that he could not demonstrate a true repentance toward what is honorable even in his last moments of life?  Would the same have been true of Saul, who shamefully persecuted the righteous Church of God, had he committed suicide from the remorse he felt for his sins after his eyes were opened to the truth, and not had the opportunity to demonstrate through his repentant life as the apostle Paul such a commitment to the noble truths of God’s kingdom that even those whom he earlier persecuted could rejoice with him in heaven?

How does this help us to understand that repentance, at least for some sins, is much more than just saying we are sorry, and is necessarily commensurate with our sins?  Think: considering the evil we now know that has come upon the world through the ideology of evolution, is it possible that Charles Darwin would ever experience the peace and joy of heaven even if he truly repented on his death-bed, without some demonstration of effort to undo the evil he unleashed?  What does this again remind us about the “grave” danger of sin, and why it is so sinful and so necessary for us to flee from it?  What does it also teach us about the evil of suicide, by which people are deceived they can escape the weight of their sins?  Much rather, in what way does suicide potentially seal their doom by preventing any opportunity to truly repent?  How does this also help us to understand the motivation of those who oppose the death penalty in favor of life imprisonment?  On the other hand, what is the Christian thing to do for a truly grievous sin but to surrender oneself, even to be hanged if necessary, and so at least acknowledge God’s justice, thereby demonstrating our repentance, if perhaps we might yet be saved by His grace, as was the thief on the cross?

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