11Woe to them! For they have gone the way of Cain . . .
“Woe” is a word Jesus used repeatedly to lay out His definitive statement of condemnation. Rational argument and debate are over, judgment is certain, and forewarning is thrown down. This is not an idle threat to win points in a discussion, but it is a “drop the mic” warning of finality.
The synoptic gospels record the word “woe” thirty times, most notably from the mouth of Jesus denouncing the religious leaders: “Woe to you, scribes and Pharisees, hypocrites . . .” (Matt. 23:13, etc.). We see the word used fourteen times in the book of Revelation, where God pronounces judgment on the wicked of the world. In the NT letters (Romans through Jude), the word occurs only one other time besides in our Jude passage. In 1 Corinthians 9:16, Paul calls down a “woe” on himself if he were to shirk his responsibility to preach the gospel. Using the word “woe” was one of the most potent ways he could call judgment on himself (see also Gal. 1:8–9).
So, Jude warns those pseudo-believers that perverting God’s grace to justify their immoral lifestyle carries eternal consequences. Even though Jude is writing to Christians, he gives words and, we could say, empowers his readers with the perspective and framework for dealing with such reprobates who are nothing more than hypocrites, posing as something they are not.
Jude likens the pseudo-believers to Cain (Gen. 4) with no further comment, assuming we all know that story well. Abel’s animal sacrifice was accepted by the Lord, whereas Cain’s grain offering was not. So Cain killed Abel and then defended himself by refusing responsibility for Abel’s well-being: “Am I my brother’s keeper?” (Gen. 4:9). Cain was self-justifying and self-centered. We can interpret from the context that his grain offering reflected a self-centered, minimal sacrifice designed to appease God rather than a genuine desire to please God in faith.
Jude infers from this comparison with Cain that pseudo-believers are self-centered, living solely for themselves and not for God. They can argue all they want, but in the end, they are under the same judgment as the legalizers. Both pervert or undermine God’s grace, and both live lives of futility! The former reject grace by their efforts to gain righteousness by keeping the law. The latter swing the pendulum to the other erroneous extreme. They assume that since God is gracious, they can appease Him simply by joining the Christian community and going through the motions of what believers do, and yet still live self-centered lives of the flesh. Those people are under God’s censure.
Lord, as Your child, I never want to hear You say to me, “Woe to you!”

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