Jesus speaks the first of eight woes to the scribes and Pharisees. It is issued because they refuse to enter God’s kingdom or to allow anyone else to enter it.
The parallel account of this remark is found in Luke 11:52.
As Jesus was speaking to the crowds and His disciples (Matthew 23:1) He warned them to not be like the scribes and Pharisees (Matthew 23:2-3). He described their false righteousness as pitiless (Matthew 23:4) and image-obsessed (Matthew 23:5). Their lust for power made them jealous of God (Matthew 23:6-10). Instead of exalting themselves as the Pharisees did, Jesus told His disciples to seek true greatness by pleasing God, through serving others in humility to God (Matthew 23:11-12).
Next Jesus began chastising the scribes and Pharisees, who were likely represented in the listening audience among the crowds, with a series of prophetic and grievous interjections. This series is often known as “The Eight Woes” (Matthew 23:13, 14, 15, 16, 23, 25, 27, 29).
A woe is a spoken interjection or sudden exclamation that interrupts the speaker’s flow of communication. It was commonly used in the ancient world. In Biblical language it conveys deep sorrow or despair. It describes the opposite state of Blessed or (in Greek, “Makarios”). And while the Eight Woes are a type of linguistic parallel it is unlikely that they are direct contrasts to the poetic eight Beatitudes that open Jesus’s Sermon on the Mount (Matthew 5:3-12). (The negative parallels to the Beatitudes are found in Luke 6:24-26). The Eight Woes do, however, provide a glimpse of the Beatitudes’ alternatives.
Today’s modern uses of the term woe are typically a humorous or a playful ironic expression of concern over our first-world problems, (i.e. “woe is me, my wifi has a slow connection”). But we should not allow our contemporary lingo to blind us from the grave warnings, the painful lamentations, or the profound sense of hopelessness that the woes of the ancient world and Bible conveyed. There was nothing playful or sarcastic about them.
The Bible typically uses woe one of two ways.
The first way the Bible uses woe is by a sufferer despairing over his disastrous circumstances. One example of this usage was when the Philistines feared the power and presence of God when the Israelite army brought the ark of the covenant into their camp: “Woe to us! Who shall deliver us from the hand of these mighty gods?” (1 Samuel 4:8a). Another example was when the prophet Isaiah became painfully aware of his sin when in the presence of God, “Woe is me, for I am ruined! Because I am a man of unclean lips, And I live among a people of unclean lips; For my eyes have seen the King, the LORD of hosts” (Isaiah 6:5).
A second way the Bible uses woe is as a prophetic warning against calamitous consequences. The majority of woes found in the Bible were warnings.
“Woe to those who call evil good, and good evil.”
“Woe to him who builds his house without righteousness
And his upper rooms without justice,
“Woe to the foolish prophets who are following their own spirit and have seen nothing.”
“Woe to the earth and the sea, because the devil has come down to you, having great wrath, knowing that he has only a short time.
The eight woes that Jesus said about the scribes and Pharisees in Matthew 23 were all prophetic warnings. At least some of these eight woes were said by Jesus on other occasions—including once when Jesus ate lunch with a Pharisee (Luke 11:37-52).
Based on what Jesus said following each woe, it is clear that He said them with great emotion. Christ’s display of emotion is another way we see that the Son of God is human. This is not meant to imply that God apart from being man is devoid of emotion such as joy or grief—only that this is one more example of how Jesus fully partook in our human likeness (Hebrews 2:17).
The emotions Jesus displayed in these eight woes appear to be anger and sadness. God cares deeply for true justice (Psalm 33:5; Isaiah 61:8). True justice is when a community cares for one another, and gives dignity and worth to each person. In order to have true justice, those in authority must care for the welfare of others. And Jesus was angry that Israel’s religious leaders were abusing His laws to act wickedly, taking advantage of those they were supposed to serve. God identifies with the suffering of the innocent, and He understands their pain (Psalm 34:18; Psalm 147:2-6; Isaiah 49:13). And Jesus lamented the great harm the Pharisees were inflicting upon His people.
The first (of eight) prophetic woes in Matthew 23 was: Woe to you, scribes and Pharisees, hypocrites, because you shut off the kingdom of heaven from people; for you do not enter in yourselves, nor do you allow those who are entering to go in.
In Luke’s gospel, Jesus said a similar woe. It chastised the “lawyers” (scribes):
“Woe to you lawyers! For you have taken away the key of knowledge; you yourselves did not enter, and you hindered those who were entering.”
This woe (like seven of the eight woes in Matthew 23) was addressed to you, the scribes and Pharisees.
The scribes were religious lawyers. They were meticulous about the moral codes prescribed by the Law (the Old Testament scriptures, especially the Books of Moses) and the Tradition (the Jewish “Mishnah” a written record of the oral teachings of Rabbis extending to Moses that was developed and codified after the Babylonian exile). The scribes searched the Law and the Tradition to create loopholes for themselves while simultaneously creating a litany of rules which they applied to control the people.
The Pharisees were the keepers and promoters of the Jewish moral culture. They led and taught in the local synagogues. They were seen as the champions and exemplars of the Jewish faith. The Pharisees strictly followed their and the scribes’ interpretations of the Law and the Tradition. And they crushed anyone who failed to follow their rules or dared defy them.
The scribes had legislative and judicial authority. The Pharisees had executive authority and power to impose the scribes’ interpretations of the law upon the people. Both colluded together to become an unopposable and corrupt force of religious malpractice.
Jesus called them hypocrites. Hypocrite comes from the Greek term for “actor.” It is someone who pretends to be one thing but is really another. It describes someone who is fake. Jesus uses this term to brand the scribes and Pharisees as religious frauds.
In His Sermon on the Mount, He used this term to denounce fake religious actions (actions that the Pharisees did) but He did not explicitly identify the Pharisees as hypocrites at that time (Matthew 6:2; 6:5; 6:16; 7:5). Later, when the Pharisees and scribes confronted Jesus about His disciples picking grains on the Sabbath (Matthew 15:7-9) and when they partnered with the Herodians to entrap Him over paying the poll tax (Matthew 22:18), Jesus was not so subtle.
In the first of eight woes, Jesus called the scribes and Pharisees, hypocrites, for how they shut off the kingdom of heaven from people. These religious leaders pretended to follow God, but in actuality they were only interested in promoting their own social fiefdoms. They rejected the Messiah and His messenger (John the Baptist) who preached of the kingdom’s coming (Matthew 3:2; 4:17). They actively strove to shut off the kingdom from the people by slandering Jesus (Matthew 12:24); by plotting how they might destroy Him (Matthew 12:14; Luke 11:53-54); and by kicking out those who confessed that He was the Messiah (John 9:22). Rather than pointing people to God, they usurped God’s place and pointed people to themselves. They usurped God’s position as Father, Leader, and Rabbi to the people.
The kingdom of heaven described the new and perfect social harmony between God and His people that Christ came to inaugurate. This harmony resulted from the reign of King Jesus. And His fundamental rule was to treat others with the same love and respect that you want for yourself (Matthew 7:12). It called people to serve the needs of everyone and to seek their best interest in love (Matthew 22:39)—including one’s enemies (Matthew 5:44), and the weak (Matthew 19:14).
The kingdom of heaven was Jesus’s central message (Matthew 4:23; 6:33; 9:35). He preached and taught kingdom values in His Sermon on the Mount (Matthew 5:3; 5:10; 5:19; 5:20; 6:10; 6:13; 6:33; 7:21). He commissioned His disciples to spread this news (Matthew 10:7; 16:19; 28:18-20). He taught about it in parables (Matthew 13:11; 13:24; 13:31; 13:33; 13:44; 13:45; 13:47; 18:23; 20:1; 22:2. And He discussed it with crowds and seekers (Matthew 8:11-12; 11:11-12; 19:23).
The core theme of Matthew’s Gospel was that Jesus was the promised Messiah who came to redeem Israel by inaugurating His everlasting kingdom.
The scribes and Pharisees rejected Jesus and His kingdom invitation through their persistent denials (Matthew 12:28; 22:3). It was their choice to follow the broad road and to enter by the wide gate, which leads to destruction (Matthew 7:13-14). In this case, the destruction included Israel’s’ opportunity to have their kingdom restored (Acts 1:6,3:19). It was their choice to not cut off things of the world from their life, and enter into fiery Gehenna whole, rather than to enter the kingdom maimed by loss in the world system (Matthew 5:29-30).
God respects everyone’s decision to follow or reject Him and His rewards. But the rejection of the Pharisees reached an elevated level, because they pretended to be close to God and support His kingdom. But Jesus pointed out you do not enter in and participate in it yourselves. This was why Jesus called them hypocrites.
Moreover, they did everything within their power to not allow those who are entering the kingdom to go in to the kingdom. They slandered Jesus and His message. And they actively persecuted those who tried to follow Him. They were stumbling blocks for the faithful.
Elsewhere Jesus warned with another woe to anyone who causes “one of these little ones” to stumble on their way into His kingdom.
“Whoever causes one of these little ones who believe in Me to stumble, it would be better for him to have a heavy millstone hung around his neck, and to be drowned in the depth of the sea. Woe to the world because of its stumbling blocks! For it is inevitable that stumbling blocks come; but woe to that man through whom the stumbling block comes!”
But despite their best efforts to not allow anyone to enter the kingdom, the scribes and Pharisees were unable to stop the work of God. The crowds were shouting, and the children were singing “Hosanna to the Son of David” (Matthew 21:9, 15). The tax collectors and prostitutes were entering the kingdom before their very envious eyes (Matthew 21:31). And the kingdom was being taken away from the scribes and Pharisees and given to a people who would produce its fruit (Matthew 21:43).
It must have seemed to them, as though the very rocks were crying out (Luke 19:40).
13 “But woe to you, scribes and Pharisees, hypocrites, because you shut off the kingdom of heaven from people; for you do not enter in yourselves, nor do you allow those who are entering to go in.
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