Woe.

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We are taking a pause from Isaiah. I really feel it is important to understand what the Lord spoke to Isaiah to reveal to the people. Today we look at what Jesus brought against the guides.

 This passage is entirely the words of Christ. This begins a stretch in Matthew’s gospel that runs through the beginning of chapter 26. It is almost entirely words spoken by Jesus. In the prior chapter, Jesus silenced the religious leaders with His astonishing responses to their questions. Here in chapter 23, He starts describing the failures of the scribes and Pharisees. They have not fulfilled their God-given roles in leading the people.

Jesus begins by acknowledging that the scribes and Pharisees carry a certain level of legitimate authority. They sit, metaphorically speaking, on “the seat of Moses.” Jesus does not tell the people to rebel against these leaders. Instead He is warning Israel not to imitate their hypocrisy. This begins a systematic take-down of their heart motives and spiritual blindness (Matthew 23:1–3).

Many people were impressed by the Pharisees’ religious deeds. Christ condemns how the scribes and Pharisees behave. They only did these deeds for themselves. Their motive is not sincere, humble service to God, but to be seen and approved of by other people. We have recently coined the buzz word “people pleasers.” This is who they really where.

Above all, Jesus says, these religious leaders live to be noticed, respected, and praised. They show off by making their wearable articles of worship ostentatious. They jockey for the most prestigious seats at feasts and in the temple. They love to be called by their official titles in the marketplace. Jesus very bluntly condemns these attitudes. His followers are told to not to make the same mistakes (Matthew 23:4–12).

Jesus then pronounces God’s judgment on these men.

We pause a moment for our own self reflection. Can we see a mirrored reflection in ourselves? What Jesus speaks next, should make us sit up a little straighter in our chairs.

God’s judgment comes through a series of seven “woe” statements about their hypocrisy. The term “woe” is more or less kept intact from the Greek ouai. The word is like other exclamations, such as “alas!” or “oh!” To capture the feel of this term, English speakers might imagine Jesus shaking His head. They could think of Him saying “ooh…this is bad.” Just as sounds like “hah!” express triumph, the word ouai expresses grief.

First Woe.

This is the first of many times in the chapter where Jesus calls the scribes and Pharisees “hypocrites.” This is derived from the Greek term hipokritēs, which literally refers to stage actors. These are people who behave in pretending, artificial ways, entirely different from their real thoughts. We like to say they are people who do not walk the talk. In this case, these are leaders who tell people to do something, while they themselves do the opposite. Their faulty leadership slams the door of eternity in people’s faces. Their choices will not lead them to heaven. Those who follow their example will also be lost (Matthew 23:13).

Verse 14, as seen in some translations, is not found in the older manuscripts of Matthew. It repeats a sentiment Jesus expressed in Mark and Luke.

40 They devour widows’ houses and say long prayers just for show. These will receive harsher judgment.”

Mark 12:40

47 They devour widows’ houses and say long prayers just for show. These will receive harsher judgment.”

Luke 20:47

The statement expressed in that verse is true, but not likely original to Matthew’s text (Matthew 23:14).

Second Woe.

Israel’s religious leaders put considerable effort into convincing others of their views. The “proselytes,” referred to here might be Gentile converts to Judaism, or Jewish converts to the Pharisaical set. All this accomplishes, ultimately, is that the converts are also damned. Jesus says such people are “twice the children of hell.” They follow false teachers and false faiths (Matthew 23:15).

Third Woe

Jesus now calls the Pharisees and scribes “blind guides.” This is a criticism He has used before.

12 Then the disciples came up and told him, “Do you know that the Pharisees took offense when they heard what you said?”

13 He replied, “Every plant that my heavenly Father didn’t plant will be uprooted. 14 Leave them alone! They are blind guides. And if the blind guide the blind, both will fall into a pit.”

Matthew 15:12-14

39 Jesus said, “I came into this world for judgment, in order that those who do not see will see and those who do see will become blind.”

40 Some of the Pharisees who were with him heard these things and asked him, “We aren’t blind too, are we?”

41 “If you were blind,” Jesus told them, “you wouldn’t have sin. But now that you say, ‘We see,’ your sin remains.

John 9:39-41

Blindness is often used in Scripture to symbolize those who reject God’s message. This rejection makes it impossible for them to perceive what is spiritually true. In this case, Christ points to their irrational approach to vows. Logically, swearing by any of the sacred objects would amount to swearing by God in heaven. Instead, the scribes and Pharisees suggest that some oaths can be easily broken. Jesus has also condemned this practice.

33 “Again, you have heard that it was said to our ancestors,

You must not break your oath, but you must keep your oaths to the Lord. 

34 But I tell you, don’t take an oath at all: either by heaven, because it is God’s throne; 35 or by the earth, because it is his footstool; or by Jerusalem, because it is the city of the great King. 36 Do not swear by your head, because you cannot make a single hair white or black. 37 But let your ‘yes’ mean ‘yes,’ and your ‘no’ mean ‘no.’ Anything more than this is from the evil one.

Matthew 5:33-37

Attempting to create loopholes in one’s integrity is not only dishonest, but also foolish (Matthew 23:16–22).

Fourth Woe.

These religious leaders carefully give ten percent of their crops. This was not wrong, as it means applying the law of Moses to the tiniest details of their lives. However, the other details of the scribes and Pharisees’ teachings left enormous aspects of God’s law unresolved. Their emphasis was on legalism, technicalities, and wooden literalism. Instead, they should have put equal emphasis on justice, mercy, and faithfulness. This error is as absurd as using a screen to clear insects out of drinking water. It is like swallowing a massive animal (Matthew 23:23–24).

Fifth Woe.

The scribes and Pharisees are committed to their public image. They go to great lengths to “look good” to other people. However, their spiritual state is one of hypocrisy and death. This is like wiping the outside of cups and dishes while leaving the insides filthy. Jesus echoes His other teachings on the subject (Matthew 15:11). He tells them to clean inside first. Then the outside will follow (Matthew 23:25–26).

Sixth Woe.

Using a second, even more graphic analogy, Jesus contrasts the Pharisees’ and scribes’ outer appearance with their inner spirits. Grave sites in that time were often covered in lime. Some even had decorative objects. These were appealing to the eye but did not change the decay and death under the surface. In the same way, the hypocrites in Israel’s religious leadership performed pious outward actions. They covered their inner hypocrisy and lawlessness (Matthew 23:27–28).

Seventh Woe.

Jesus concludes the “woes” by showing that the Pharisees claim to honor the prophets of old. However, they are just as guilty as their own forefathers. Those forefathers persecuted and killed messengers from God. God’s measure of wrath eventually reaches a tipping point. For that reason, Jesus states that this generation of Israel’s religious leaders will experience consequences. They will suffer due to the many righteous people unjustly killed throughout their history. They will not change their ways. This hateful persecution will continue in the years after Jesus is crucified and raised from the dead (Matthew 23:29–36).

Matthew 23 ends with Jesus’ lament over Jerusalem. Speaking from His divine perspective, He mourns over how He would have protected the people, but they refused.

39 You pore over the Scriptures because you think you have eternal life in them, and yet they testify about me. 40 But you are not willing to come to me so that you may have life.

John 5:39-40

This is the end point of Jesus’ public ministry. The following chapters contain extensive teachings given to the disciples, but no more public lessons or encounters. There will be no more opportunities for the people to hear directly from Him. Worse, the city will soon experience horrific wrath as the protection of God is removed.

24 As Jesus left and was going out of the temple, his disciples came up and called his attention to its buildings. He replied to them, “Do you see all these things? Truly I tell you, not one stone will be left here on another that will not be thrown down.”

Matthew 24:1-2

The next time the people of Jerusalem will see Jesus openly will be when He returns. He will come as a conquering Judge and King (Matthew 23:37–39).

SO how do we put this together?

Look back over yesterday’s list of God’s charge over the guides and today’s scripture over what Jesus charged against the guides.

Consider the guides in our lives. Are they godly or worldly. Who’s advice are you listening to? Is it godly or worldly.

Consider who you are a guide to. It does not have to be a formal teacher/student relationship. Think about the relationships of influence.

IS the Holy Spirit convicting you of anything in the ways that you are lead or in the way you lead and guide others.

What warning does God give to the blind guides?

© Kimberlee Smith 2025 http://www.itstartssmall.com All rights reserved. 
 


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