In the final few days of Jesus’ life on earth, He did not hold anything back. Time was limited before He was to be crucified and sacrifice Himself for the sins of all men for all time. Realizing that His time was near, on Sunday He enters Jerusalem and was accepted by the crowd, and on Monday curses a fig tree establishing Himself as the final judge. Now, On Tuesday, He preaches as a prophet of old scribing “woe” after “woe” condemning the attitudes and behaviors of the established religious leaders. His warnings in Matthew 23:13-36 contain seven or eight “woes” depending on your translation. These eight “woes” serve as a warning against hypocrisy and false religious piety. Eight times Jesus says to them, “Woe to you, scribes and Pharisees, hypocrites.” More than any other group, the scribes and Pharisees were false teachers. While some were sincere and true such as Nicodemus, the majority had traded in the truths and wisdom of God for the traditions and wisdom of men.
Jesus’ language was not from personal irritation but from divine godly warnings of condemnation. A series of “woes” was common from the Old Testament prophets. Isaiah lays down woe after woe to those who were wicked and evil (Isaiah 5:8-20). Habakkuk sharply criticizes those who cheat and hurt others with the word, “woe”, again and again (Habakkuk 2:6-19). For Jesus, the greatest prophet to have ever preached, it only seems natural for Him to have moments when a “woe”, or two, or eight would be appropriate. These “woes” are to be heard because He is the Messiah!
The word “woe” (ouai) is used in several ways. Most often it is a loud guttural outcry of pain, fear, or anger. The prophet might cry out, “WOE!” with a growling gruff voice. It could also be used as an expression with gentleness showing grief, despair, or sorrow, as in, “Woe is me”. It seems most appropriate to interpret the “woe” here in Matthew 23 as one of judgment mixed with regret. Perhaps Jesus is saying “woe” with this guttural outcry. Jesus is not using it as an exclamation, but rather as a declaration of divine judgment convicting sinful men who will not turn from their evil, hypocritical ways.
Jesus calls them “hypocrites” (hupokritis) at each “woe”. This word, hypocrite, has been used to describe someone who speaks or acts under a false part. The hypocrite takes on an assumed character. The hypocrite is a stage player; dissembler; or a pretender. A hypocrite is a person who lives the lie, for they are not what they seem to be to others. The word had been used by Greek actors who placed a mask over their faces as they played their parts. From that usage, the word developed a meaning of someone who pretended to be something they were not, and specifically, someone better than they really were. Outwardly appearing in public to be of high virtue, but inwardly and in private proving to be immoral. This was an accurate description of most of the scribes and Pharisees. Jesus is exposing the underlying corruption covered by the spiritual image of these “religious leaders”.
As Jesus begins this series of “woes” He is calling out and correcting the attitudes and actions of those scribes and Pharisees who have hypocritical tendencies. H. Leo Boles says, “The dark clouds begin now to gather around the great central truth of Jesus’ teaching — His crucifixion; He concludes His teaching with these sublime wails over the wickedness of the world as is personified in the scribes and Pharisees.” His message is relevant for the church today as well.
Hopefully, it serves as a warning for us too, to watch our attitudes and actions and steer clear of hypocritical Christianity.
Let me encourage you to take the time to read and study this passage on your own time and reflect on this as one of Jesus’ final lessons before this death. If these are some of Jesus’ final words it must have been important for it to have been said and for us to read and heed today.