In Matthew 23, Jesus pronounces seven “woes” on the religious leaders of His day. A “woe” is an exclamation of grief, similar to what is expressed by the word alas. In pronouncing woes, Jesus was prophesying judgment on the religious elite who were guilty of hypocrisy and sundry other sins.
The King James Version and some other translations list eight woes in Matthew 23, but older manuscripts leave out verse 14, in which the scribes and Pharisees are condemned for taking advantage of widows and making lengthy prayers for show. Elsewhere, Jesus speaks against those very sins (Mark 12:40 and Luke 20:47); most likely, however, Matthew did not include them among the other woes of chapter 23.
The seven woes are addressed to the teachers of the law and Pharisees; in one of the woes, He calls them “blind guides” (Matthew 23:16). At the end of His denunciations, He calls them “snakes” and “brood of vipers” (verse 33). Prior to Jesus’ condemnation of the religious hypocrites, they had been following Him to test Him and try to trick Him with questions about divorce (Matthew 19:3), about His authority (Matthew 21:23), about paying taxes to Caesar (Matthew 22:17), about the resurrection (verse 23), and about the greatest commandment of the law (verse 36). Jesus prefaced His seven woes by explaining to the disciples that they should obey the teachings of the Jewish leaders—as they taught the law of God—but not to emulate their behavior because they did not practice what they preached (Matthew 23:3).
The first of Jesus’ seven woes condemned the scribes and Pharisees for keeping people out of the kingdom of heaven: “Woe to you, teachers of the law and Pharisees, you hypocrites! You shut the door of the kingdom of heaven in people’s faces. You yourselves do not enter, nor will you let those enter who are trying to” (Matthew 23:13). Jesus is the only Savior and the only way to heaven. In their rejection of Jesus Christ, the Pharisees were effectively refusing to enter the kingdom of heaven. They also hindered the common people from believing in Him, thereby blocking the way to heaven for others. Repentance and faith in Christ is the door of admission into this kingdom, and nothing could be more disagreeable to the Pharisees, who saw no need for repentance in their own lives and attempted to justify themselves by strict adherence to the law.
In the second of the seven woes, Jesus condemned the leaders for teaching their converts the same hypocrisy that they themselves practiced. They led their converts into a religion of works, but not into true righteousness, making them “twice as much a child of hell” (Matthew 13:15).
The third woe Jesus pronounced referred to the religious elite as “blind guides” and “blind fools” (Matthew 23:16–17). The hypocrites fancied themselves guides of the blind (see Romans 2:19), but they themselves were blind and therefore unfit to guide others. Their spiritual blindness caused them to be ignorant of many things, including the identity of the Messiah and the way of salvation. They were blind to the true meaning of Scripture and to their own sin. They purported to guide the people into the truth, but they were incapable of doing so because they had no personal knowledge of the truth. Instead of teaching spiritual truth, they preferred to quibble over irrelevant matters and find loopholes in the rules (Matthew 23:16–22).
The fourth of the seven woes called out the scribes and Pharisees for their hypocrisy in the practice of tithing. They made a big deal of small things like tithing spices, while they ignored crucial matters. They diligently counted their mint leaves to give every tenth one to the temple, but they “neglected the more important matters of the law—justice, mercy and faithfulness” (Matthew 23:23). Turning to hyperbole, Jesus said, “You strain out a gnat but swallow a camel” (verse 24). In other words, they were careful to avoid offense in minor things of little importance (straining gnats), while tolerating or committing great sins (swallowing camels).
In the fifth, sixth, and seventh woes, Jesus further illustrated the different aspects of hypocrisy that characterized the religious leaders. In the fifth woe, Jesus likened them to dishes that were scrupulously cleaned on the outside but left dirty inside. Their religious observances made them appear clean and virtuous, but inwardly their hearts were full of “greed and self-indulgence” (Matthew 23:25).
In the sixth woe, Jesus compared them to “whitewashed tombs, which look beautiful on the outside but on the inside are full of the bones of the dead and everything unclean” (Matthew 23:27). The rotting corpse inside a tomb was like the hypocrisy and lawlessness in the hearts of the scribes and Pharisees. They appeared righteous on the outside, but they were just beautified tombs; inwardly, they were spiritually dead.
The hypocrisy Jesus addressed in the seventh woe was directed to those who erected monuments and decorated the tombs of the prophets of old. Jesus points out that those prophets had been slain by the Pharisees’ own ancestors. They imagined themselves much better than their fathers, saying, “If we had lived in the days of our ancestors, we would not have taken part with them in shedding the blood of the prophets” (Matthew 23:30). But in that very statement they acknowledged their lineage: Jesus says they were truly their fathers’ sons; they had inherited their ancestors’ wickedness and were following in their steps. Jesus knew their evil hearts, which would soon plot to murder Him (Matthew 26:4) just as their ancestors had murdered the righteous men of old.
The seven woes of Matthew 23 were dire warnings to the religious leaders of Jesus’ day. But they also serve to warn us against religious hypocrisy today. We are called to true godliness, sincere love, and enduring faith. Pretension, affectation, and hypocrisy will only lead to woe.