Only Matthew records this scathing denunciation of these religious leaders of the Jews. These woes, in contrast to the Beatitudes, denounce false religion as utterly abhorrent to God and worthy of severe condemnation. No passage in the Bible is more biting, more pointed, or more severe than this pronouncement of mashiach ישו נוצרי (Christ) upon the Pharisees. It is significant that He singled them out, as opposed to the Sadducees, who were more liberal, and the Herodians, who were the politicians. The Pharisees, while attempting to honor the Word of God and manifesting an extreme form of religious observance, were actually the farthest from God.
His first condemnation, in 23:13, related to the fact that they did all they could to shut out others. False religion and pretense are always the worst enemies of the truth and are far more dangerous than immorality or indifference. As the religious leaders of the Jews, they were held guilty before God of blocking the way for others seeking to enter into the Kingdom of God.
In verse 14, the first woe is indicated, in which the scribes and Pharisees were charged with devouring widows houses and making long prayers to impress others. The verse, however, is omitted in most manuscripts and probably should not be considered as rightly a portion of this Scripture. It may have been inserted from Mark 12:40 and Luke 20:47. If it is included, it would bring the total woes to eight instead of seven.
In Matthew 23:15, the second woe is mentioned. In this one, the Pharisees were described as extremely energetic on both land and sea to make proselytes of the Jewish religion. But when they were successful, Yeshua charged, Woe to you hypocritical Torah-teachers and Prushim! You go about over land and sea to make one proselyte; and when you succeed, you make him twice as fit for Gei-Hinnom as you are!" In referring to hell, Christ used the word Geenna or Gehenna, a reference to eternal damnation, rather than to Hades, the temporary abode of the wicked in the intermediate state. The Pharisees and their proselytes both would end up in eternal damnation.
A third woe is mentioned in verse 16, based on the trickery of the Pharisees, who held that swearing by the gold of the temple bound the oath. Yeshua denounced them as both fools and blind, as obviously the gold was meaningless unless it was sanctified by the temple, and the gift on the altar was meaningless unless it was given significance by the altar. Repeating His accusation, He declared in verse 19, "Blind men! Which is more important? the sacrifice? or the altar which makes the sacrifice holy?" Accordingly, Yeshus concluded that an oath based on the temple was binding, just as an oath based on heaven carried with it the significance of the throne of God and God who sits on the throne.
The fourth woe, mentioned in verse 23, has to do with hypocrisy in tithing. While they were so concerned in paying the tithe down to the smallest spice or seed, they omitted the really important matters: obeying the law and manifesting mercy and faith. He repeated His charge that they were blind, straining out a gnat or a small insect, but swallowing a camel. He was, of course, speaking figuratively of their dealing with minutiae but omitting the really important things.
The fifth woe is pronounced in verse 25, where He repeated the charge that they were hypocrites, merely actors acting a part. He charged them with cleaning the outside of the cup and the platter but being unconcerned about what was inside, where cleanliness really matters. He meant by this that they were concerned with ceremonial cleanliness, that which men observed, but not really concerned with holiness. While observing ceremonial rites of cleansing, they were not above extortion and excess.
In verse 27, Yeshua mentioned the sixth woe. In this one, He described them as whited sepulchres, graves that had been made beautiful and white on the outside but within were full of dead mens bones. This illustrated that the Pharisees were outwardly righteous but inwardly full of hypocrisy and iniquity.
Yeshua concluded with the seventh woe, in verse 29, in which He charged them with building tombs of the prophets and garnishing them with decorations and claiming that they would not be partakers with their fathers in martyring prophets. Yeshua called their very witness to account, that they were the children of those who killed the prophets, and He told them, in verse 32, "Go ahead then, finish what your fathers started!" In other words, do what your fathers did and even do worse. Yeshua was, of course, referring to their intent to kill Him and to their later persecution of the church.
In the severest terms, in verse 33, Yeshua addressed them, You snakes! Sons of snakes! How can you escape being condemned to Gei-Hinnom?" He described the scribes and Pharisees as poisonous snakes, destined for terrible judgment which would be theirs in hell, specifically Gehenna, the place of eternal punishment. Yeshua declared, in verse 34, that He would send to them prophets, wise men, and scribes who were also believers. Some of them they would persecute, some they would scourge and drive out of the synagogue, and others they would kill and crucify. Their works would justify bringing upon them the just condemnation coming from all the righteous blood shed upon the earth from the time of righteous Abel, killed by Cain (Gen 4:8), to the martyrdom of Zacharias, the son of Barachias (2 Ch 24:20-22). Zacharias, mentioned as the son of Jehoiada in 2 Chronicles 24:20, probably was the grandson of the priest and Barachias was his actual father.
The sad chapter in the days of Israels apostasy was the climax of the religious rulers long rejection of the things of God. Yeshua solemnly pronounced that all these acts of rejection of God and His prophets would cause judgment to come upon this generation, which they would bring to culmination by their rejection of Gods only Son. This prophecy was tragically fulfilled in the destruction of Jerusalem and the scattering of the children of Israel over the face of the earth. Jerusalem, the city of God, and the magnificent temple, the center of their worship, were to lay in ashes as an eloquent reminder that divine judgment on hypocrisy and sin is inevitable.