In the first twelve verses of Matthew chapter 23, Jesus identified five marks or characteristics of a false leader – identifying them by: (1) the works they do, (2) the burdens they render, (3) their need for an audience, and (4) their love of honor and titles; all of these ultimately point to the 5th mark – pride. These were the characteristics of the religious leaders in Jesus’ day – the scribes and Pharisees. While some of them may have been charlatans and con men, most of them, as most false teachers in our day, believed they were serving God, even as they actually worked against Him.
Jesus followed his indictment in verses 13-33, with some of the most polemical and scathing words he has ever spoken. In light of Jesus’ command to love our enemies, some have stumbled over these words, even to the point calling into question their authenticity. But when we consider His prodigious love for His people and the sway that human leaders have over them, we can understand how the righteous indignation that Jesus Christ had toward these leaders would result in the harshest of condemnation against them. Sometimes shocking words are required, especially toward the wayward leaders of God’s flock.
Jesus’ condemnation against these scribes and Pharisees come in the form of seven “woes,” which flesh out Jesus’ previous statement, “whoever exalts himself will be humbled (23:12).” A “woe” is an expression of pain, wrath and sorrow that is typically organized into three parts: (1) the recipient of the judgment; (2) the transgression for which the judgment comes; and (3) the resulting condemnation. “Woes” serve as the opposite of “blessings;” as blessings convey salvation to the contrite, woes communicate judgment to the prideful and unrepentant. In these seven woes pronounced by Jesus to the religious leaders of the Jewish people, we find them to be false proselytizers (v. 13-15) with false priorities (v. 16-24) coming under false pretense (25-28) as a result of a false pedigree (29-33).
Matthew 23:13-33 concludes the section which began in chapter 21, exposing the false shepherds of Israel; but it also serves as a bridge to the impending judgment on Israel and eschatological events leading to Judgment day, unpacked in the Olivet Discourse of chapters 24-25. Though talk of wrath and judgment and an ultimate Judgment Day may not be comfortable for us as Christians, the holiness of God necessitates our assimilating words of judgment into our understanding.