Down to Earth But Heavenly Minded

What Does Matthew Chapter 23 Mean?

Other than the introductory sentence, this passage is entirely the words of Christ, as with John chapter 17. This begins a stretch in Matthew’s gospel running through the beginning of chapter 26, which 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 begins to describe various ways in which the scribes and Pharisees have failed in 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. Rather, He warns 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, however, since they do everything for the wrong reasons. Their motive is not sincere, humble service to God, but to be seen and approved of by other people. 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 bluntly condemns these attitudes and tells His followers not to make the same mistakes (Matthew 23:4–12).

At this point, Jesus pronounces God’s judgment on these men. This 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!” English speakers might image Jesus shaking His head while saying “ooh…this is bad,” to capture the feel of this term. 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. 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, and those who follow their example will be lost, as well (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 12:40 and 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,” since they’re following false teachers and following a false faith (Matthew 23:15).

Third Woe

Jesus now calls the Pharisees and scribes “blind guides.” This is a criticism He has used before (Matthew 15:12–14; John 9:39–41). Blindness is often used in Scripture to symbolize those who reject God’s message, making 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 imply that some oaths can easily be broken, a practice Jesus has also condemned (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, even the tiniest herbs. 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, while 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. Echoing His other teachings on the subject (Matthew 15:11), Jesus tells them to clean inside first and 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 era were often covered in lime, and some 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 used pious outward actions to cover 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, but they are just as guilty as their own forefathers who persecuted and killed messengers from God. God’s measure of wrath eventually reaches a tipping point. For that reason, Jesus declares that this generation of Israel’s religious leaders will suffer the consequences of the many righteous people unjustly killed throughout their history. Far from changing 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 (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 (Matthew 24:1–2). The next time the people of Jerusalem will see Jesus, openly, will be when He returns (Revelation 19:11–15) as a conquering Judge and King (Matthew 23:37–39).

Chapter Context
Matthew 23 concludes Matthew’s multi-chapter account of all of Jesus’ interactions in the temple during the last week before His arrest and crucifixion. After silencing the religious leaders with parables and brilliant responses (Matthew 21—22), He pronounces God’s judgment on the scribes and Pharisees in a series of seven “woe to you” statements. Jesus mourns for the judgment that will come on Jerusalem for her rejection of God. This leads Jesus to leave the temple, sadly remarking on its impending destruction (Matthew 24:1–2). As the disciples ask about this, Jesus begins an extended teaching on the end times in chapter 24.

Verse By Verse

Verse 1 Then Jesus said to the crowds and to his disciples,

Matthew has been reporting on Jesus’ conversations and teaching in the temple for much of the previous two chapters (Matthew 21—22). Christ’s main topic has been the spiritual corruption of Israel’s religious leaders. That exposition has included several parables and taking questions from representatives of the various groups of religious rabbis and officials. In this passage, He begins describing even more forcibly the consequences for the failings of the scribes and Pharisees.

He is speaking both to the crowds gathered at the temple for the Passover celebration, as well as to His own disciples. Perhaps some of the religious leaders are continuing to listen to Jesus, as well, though they are not mentioned. It’s possible they have left after being so thoroughly dismantled in debate (Mathew 22:46), or they might be lurking around and listening without interacting.

Verse 2 “The scribes and the Pharisees sit on Moses ‘ seat,

Jesus will soon deliver a series of “woes” to the scribes and Pharisees, describing their failings and corruption in the harshest of terms. Since it is coming from Jesus, this condemnation of Israel’s religious leaders is delivered as the condemnation of God Himself (John 5:30; 10:30; 14:9).

He begins, though, with a statement of respect for the positions occupied by these two groups. Jesus describes them as sitting “on Moses’ seat.” Some scholars suggest Jesus is referring to a literal chair occupied by religious leaders while teaching. More likely, Jesus is speaking of the authority given to the scribes and Pharisees by God, as it was given to Moses. That authority would be used to teach the people from the Scriptures and to lead them in the way they should go.

The group referred to as “scribes” were experts in Jewish Scriptures. They were educated and intelligent men often occupying official teaching positions in Jewish religious life. Pharisees were more likely to teach the theology and meaning of the Scriptures than the basic content. Pharisees had much influence over the religious lives of the everyday people. Likely, some overlap existed between these two groups.

Verse 3 so do and observe whatever they tell you, but not the works they do. For they preach, but do not practice.

Matthew has been clear that Jesus is speaking to the crowds gathered in the temple who are listening to Him, as well as to His own disciples (Matthew 23:1–2). What He says in this verse seems surprising, given His overwhelming condemnation of the scribes and Pharisees throughout the rest of the chapter. These men occupy “Moses’ seat,” meaning they were responsible for teaching the people of Israel how to properly understand and apply the Scriptures. Jesus tells His audience to do “and observe” what they teach, but not to follow the example of their actions.

In other words, Jesus is careful not to invalidate the role given to these men by God. He also endorses the heart of their teaching from the Torah, the Jewish Scriptures, though He will reject their teaching about matters beyond the Scriptures. He is not giving His listeners permission to turn their backs on the teaching of God’s Word. Nor is He invalidating all spiritual authorities. On the contrary, Jesus is condemning the religious leaders of His era for failing to meet their very reasonable obligations.

Though He accepts the idea of religious leaders and teachers, Jesus bluntly tells those listening to not follow the example of that generation of scribes and Pharisees. He will call them hypocrites repeatedly (Matthew 23:13, 15, 23, 25, 27, 29). Here Jesus previews that idea, though not using that exact word: “They preach, but do not practice.” This matches the Greek word hipokritēs, which literally means “an actor.” These spiritual guides live in a game of “make believe,” or “let’s pretend.” The people of Israel should not live as these men do.

Verse 4 They tie up heavy burdens, hard to bear, and lay them on people ‘s shoulders, but they themselves are not willing to move them with their finger.

Jesus has stated bluntly that the scribes and Pharisees, Israel’s primary religious leaders for everyday life, do not practice what they preach. He has told His disciples and the crowds to obey their teaching about the Scripture itself, since God has established the idea of spiritual authorities and teachers (Matthew 23:2–3). However, those same men live in contradiction to what they claim to believe. They say one thing yet do something else. They are pretending, which is the essential meaning of the Greek term hipokritēs (Matthew 23:13).

Here, that hypocrisy is being explained. Jesus is referring to the massive, complicated religious rules added to the law of Moses over time. These rules began with a good intent: to help people apply the law to everyday circumstances, and especially to help them avoid breaking it. Unfortunately, those traditional rules, created by mere human beings, had gradually been elevated until they were considered equal to the law itself.

The scribes and Pharisees insisted every follower of the law was expected to keep all these rules to be pleasing to God. Jesus notes these leaders won’t make the slightest effort to ease that burden. This does not mean the scribes and Pharisees did not keep those same rules themselves. Rather, these teachers were not willing to lighten the burden of man-made and man-controlled rules. Not even a little bit. They were not trying to help the people live out God’s Word in a way that reflected God’s heart. They only made the lives of the people more and more difficult by making religion more and more legalistic and restrictive.

Verse 5 They do all their deeds to be seen by others. For they make their phylacteries broad and their fringes long,

The scribes and Pharisees, Israel’s religious leaders, fail to practice what they preach. Jesus is describing the hypocrisy behind their very religious public appearance (Matthew 23:1–4).

Here, Jesus addresses their motives. They may do what is right or religious, according to their own interpretations, but they do so to be seen by others. They want approval and recognition of the people: to be heralded as good and religious men. One way they exhibit this is by their outward appearance. These included religious emblems such as phylacteries and fringes.

Phylacteries are known today as “tefillin.” They are small leather boxes containing pieces of parchment with Scripture written on them. The phylactery boxes were strapped to the left arm or forehead in literal obedience to Deuteronomy 11:18. The Scriptures inside were from Exodus 13 and Deuteronomy 6.

Fringes, or tassels, are dangling bits of thread, with a blue cord, attached to the four corners of a Jewish man’s garment in obedience to Numbers 15:38–39: “Tell them to make tassels on the corners of their garments throughout their generations, and to put a cord of blue on the tassel of each corner. And it shall be a tassel for you to look at and remember all the commandments of the Lord, to do them.”

It’s important to note that Jesus does not condemn the wearing of phylacteries or fringes. The objects are not wrong, and neither is their use. Rather, He calls out religious leaders for making an excessive show of those objects: wearing large, broad phylacteries and extended fringes so everyone will notice them. Their intent is not primarily to honor God; it’s to get credit from other men for being extra religious and good. They had lost sight of the proper motive for these religious objects: a reminder of the law.

Verse 6 and they love the place of honor at feasts and the best seats in the synagogues

The motive behind the public image of the scribes and Pharisees is selfishness, says Jesus. They do their good deeds to be seen and applauded by others. The actions are good, in and of themselves, but are done to gain the approval of men. To be noticed for their religiosity, they make sure the required articles of worship they wear are oversized (Matthew 23:1–5).

Further, these religious leaders love being recognized for their religiosity, including special privileges. The most honored seats at banquets were those closest to the host. Similarly, the esteemed positions in the synagogue were probably those closest to the scrolls of the law, or the most visible. At another time, Jesus responded to some who were jockeying for the most honored seats at a banquet by telling the people this in Luke 14:8–11:

“When you are invited by someone to a wedding feast, do not sit down in a place of honor, lest someone more distinguished than you be invited by him, and he who invited you both will come and say to you, ‘Give your place to this person,’ and then you will begin with shame to take the lowest place. But when you are invited, go and sit in the lowest place, so that when your host comes he may say to you, ‘Friend, move up higher.’ Then you will be honored in the presence of all who sit at table with you. For everyone who exalts himself will be humbled, and he who humbles himself will be exalted.”

The Pharisees looked for ways to exalt themselves, rather than for ways to express humility.

Verse 7 and greetings in the marketplaces and being called rabbi by others.

Jesus is describing the hearts and motives of some of the most respected men in Israel: the religious leaders known as scribes and Pharisees. He is exposing them as men who crave attention and honor; they only do good deeds to receive the praise of other men. In every way, these religious men serve their pride above all else. Status and position drive their actions (Matthew 23:1–6).

These self-important men also love the public attention brought by their positions as holy men. They love to be given grand greetings and deference in public places. They love the title that comes with their status: “rabbi,” meaning “teacher.” This was a title of respect and sometimes affection for the religious men who taught the law to the people.

Titles, themselves, are not necessarily wrong. But placing undue emphasis on them—or insisting on them—is arrogance and hypocrisy for a follower of Jesus. Christ will instruct His disciples to avoid using names and titles in ways meant to elevate one person over another (Matthew 23:8).

Verse 8 But you are not to be called rabbi, for you have one teacher, and you are all brothers.

In painful detail, Christ has been describing how the scribes and Pharisees are driven by their own pride. They seek status and respect from the people above everything else. This—not devotion to God—is their true motive for doing good works. They love special privileges, the deference of other people and so forth. They covet the title that comes with their position: “rabbi,” given to those who have been designated as Israel’s teachers of the law (Matthew 23:1–7).

Jesus pauses His condemnation of the Pharisees and scribes to warn His disciples against this practice. He commands them not to call each other “rabbi” for two reasons. First, Jesus insists they have only one teacher, meaning Him. Jesus is the only rabbi among them. Second, they are all brothers. Jesus forbids them from taking titles meant to elevate one of them over the others.

This is not a condemnation of all spiritual authority, or all titles, of any kind. Nor is Jesus’ comment in the next verse meant to forbid all use of the word “father” (Matthew 23:9). Rather, Jesus does not want His followers to be driven by pride of position or the arrogance of power. He wants us to remain humble as we serve each other in love. Seeking or proclaiming a title, for the sake of personal honor, is contrary to the humility expected of Christians.

Verse 9 And call no man your father on earth, for you have one Father, who is in heaven.

Jesus has paused from exposing and condemning the Pharisees and scribes to command His disciples to do one thing differently in the future. He has said that these official “teachers” of Israel love the title of “rabbi.” It means they have achieved a level of status in Judaism that comes with power over others. It feeds exactly what drives them: their own thirst for recognition and honor. In contrast, Jesus has told the disciples not to call anyone “rabbi.” For one thing, they have only one teacher: Jesus Himself. For another, they are all brothers. He does not want them taking positions of status and authority above each other.

In addition, Christ tells His disciples not to address anyone as “father” on earth. This is because they have a Father in heaven, meaning God, Jesus’ own Father. Jesus does not mean no one may refer to a parent as “father.” He is specifically addressing the practice of referring to religious leaders and mentors as “father” in any formal or official sense. What’s forbidden is an attempt to give one of Jesus’ followers a spiritual status above that of others.

It’s suggested that great teachers or rabbis of the past, along with the patriarchs of Israel, were sometimes called “the fathers” during Jesus’ era. Jesus wants that name—and more importantly, that reverent attitude—to be reserved for God alone.

This does not forbid anyone from occupying positions of authority in the church. In fact, Jesus has given and will continue to give great authority to His disciples, who will become known as the apostles. The danger being condemned is in using titles as the Pharisees used them: to draw praise and honor to themselves and to buttress their own authority. Jesus emphasized to His disciples repeatedly that, in His kingdom, leadership always takes the form of servanthood (John 13:12–16; Matthew 23:11).

Verse 10 Neither be called instructors, for you have one instructor, the Christ.

Jesus is forbidding His disciples from using names of honor and authority in the same manner as the Pharisees and scribes. Those prideful men loved to hear themselves referred to as “rabbi” while being greeted in the marketplace. Their pride and hunger for status drove every choice they made. His disciples were told not to be called “rabbi,” because there is only one teacher, meaning Jesus Himself. He has told them to call no man “father” on earth because they have one Father, God Himself, who is in heaven (Matthew 23:1–9).

Beyond that, Jesus adds they should not even be called “instructors,” because they have only one instructor, the Christ. Again, Jesus is referring to Himself. As He continues to near His own crucifixion (Matthew 16:21), He becomes more and more vocal in declaring Himself the Messiah. This time, He boldly declares Himself to be “the Christ.” The word for “instructor” is different from the word for “rabbi,” but both can be understood as teacher.

The point of these commands is that titles should not be used, or demanded, to have status and authority over each other. The point is not that it’s forbidden for Christians to use terms like “teacher” or “father” in any circumstance. Instead, they should continue to seek out roles as humble students to the one true rabbi and instructor, Jesus. Even those who are in authority, or those who do teach, should approach those roles as servants, not as celebrities (John 13:12–16; Matthew 23:11).

Verse 11 The greatest among you shall be your servant.

This repeats something Jesus has said several times to His disciples: that greatness in the eyes of God is different from greatness in the eyes of men (Matthew 19:30; 20:16). In fact, the most godly role to which one can aspire is to be a servant to others (John 13:12–16). This perspective is given in a clear context, and a clear contrast. Jesus has just forbidden His disciples from taking titles for the sake of worldly honor, as the scribes and Pharisees were doing.

Not long before this, Jesus explained this same concept in detail. This was in response to arguments between the disciples about which would take the greatest positions in His kingdom:

“You know that the rulers of the Gentiles lord it over them, and their great ones exercise authority over them. It shall not be so among you. But whoever would be great among you must be your servant, and whoever would be first among you must be your slave, even as the Son of Man came not to be served but to serve, and to give his life as a ransom for many.” (Matthew 20:25–28)

Verse 12 Whoever exalts himself will be humbled, and whoever humbles himself will be exalted.

Jesus has just repeated to His disciples that the greatest among them would be servant to the others (Matthew 20:26). This is the way of His kingdom. They will not find greatness in titles or seats of honor or the respect of other men. Greatness in His kingdom is only to be found in service (Matthew 23:11).

The phrase given here could be read as a proverb: Those who seek prestige will find shame, and those who seek humility will find honor. This is more than a simple command from the Lord to be humble. It is a reminder that God works to humble—to lower, to shame—those who try to exalt themselves. At the same time, God works to lift up—to honor—those who intentionally serve others with a humble spirit.

Peter heard this from Jesus with his own ears. Later, he will write something similar in 1 Peter 5:6: “Humble yourselves, therefore, under the mighty hand of God so that at the proper time he may exalt you.”

As Paul will write to the Philippians, this is exactly what happened to Jesus:

“And being found in human form, he humbled himself by becoming obedient to the point of death, even death on a cross. Therefore God has highly exalted him and bestowed on him the name that is above every name, so that at the name of Jesus every knee should bow, in heaven and on earth and under the earth, and every tongue confess that Jesus Christ is Lord, to the glory of God the Father” (Philippians 2:8–11).

Context Summary
Matthew 23:1–12 begins Jesus’ condemnation of Israel’s religious leaders, summarized with the phrase “the scribes and the Pharisees.” He warns those listening not to follow their example, since they don’t practice what they preach. Their words imply heavy burdens, but their actions don’t reflect the same. They make no effort to help others fulfill those requirements. In fact, everything they do is for show: only to be seen and approved of by others. They make a great show of religious clothes and symbols, jockey for the seats of honor everywhere they go, and take enormous pride in their prestigious spiritual titles.

Verse 13 “But woe to you, scribes and Pharisees, hypocrites! For you shut the kingdom of heaven in people ‘s faces. For you neither enter yourselves nor allow those who would enter to go in.

Over the past few chapters, Jesus has engaged in debates and dialogues with His critics, including the Pharisees and scribes. Pharisees were legalistic Jews popular with the common people for their apparent piety. Scribes were the professional interpreters of Old Testament law and traditional commentary on it. These two groups, collectively, formed the core of Israel’s spiritual leadership in the era of Jesus. After exposing their hypocrisy, Christ now begins to pronounce a series of condemnations on them.

This passage amounts to God’s official rejection of these religious leaders of Israel. Jesus uses the phrase “woe to you” seven times. Those words evoke the Old Testament prophets who pronounced God’s judgment on Israel hundreds of years earlier. The Pharisees who heard Jesus saying “woe to you” would have fully understood the connection to earlier declarations from God’s messengers to Israel.

Jesus begins by calling them “hypocrites.” Hipokritēs is a Greek word originally used for play-actors. In completely literal terms, this means someone who pretends to be what they are not for the purpose of telling a story. Over time, the English transliteration of the word has also come to mean someone who claims to believe one thing, but does the opposite.

The first condemnation is for the scribes and Pharisees shutting the kingdom of heaven in people’s faces. This colorful and descriptive word picture reveals a tragic scenario. The job these men were supposed to do was to show the people the way into the kingdom of heaven. This should have been through faith in and obedience to God. Instead, they built and enforced a mountain of additional rules, while securing their own power and status. Worse, when Jesus arrived as the Messiah to show the way to the kingdom, the Pharisees and scribes rejected Him. This ensured that they and those who followed their teaching would never enter the kingdom.

Those who should have been guides and gatekeepers had come to block the gate, keeping God’s people out instead of welcoming them in.

Verse 14 Woe unto you, scribes and Pharisees, hypocrites! for ye devour widows’ houses, and for a pretence make long prayer: therefore ye shall receive the greater damnation. (KJV)

Scholars report that the earliest and best manuscripts of Matthew do not include verse 14. For this reason, it’s skipped or included in brackets in many modern translations, including the ESV and the NIV. The words of this verse are included in Mark 12:40 and Luke 20:47; both are instances where Jesus was criticizing the hypocrisy of the scribes and Pharisees. That such an occurrence is so rare demonstrates how remarkably consistent the New Testament Scriptures have been preserved from the earliest known manuscripts to those copied later.

The sentiment recorded in some translations of Matthew 23:14 is not false, it is simply out of place. These are words of Christ, as reported by Mark and Luke. Throughout this passage, Jesus pronounces “woe” on the scribes and Pharisees. For their offenses, their condemnation at the judgment would be even greater.

The Pharisees “devoured” the homes of widows by placing large burdens on these famously poor and overlooked members of society. Or, by failing to protect them from the burdens placed on them by others. After losing their husbands, widows were in danger of losing their entire livelihood, if those resources were not carefully managed. Israel’s religious leaders should have stepped in to help these struggling women, rather than taking advantage of them to enrich the temple.

Verse 15 Woe to you, scribes and Pharisees, hypocrites! For you travel across sea and land to make a single proselyte, and when he becomes a proselyte, you make him twice as much a child of hell as yourselves.

These are some of Christ’ harshest words against the religious teachers of ancient Israel. This is the second of seven statements of judgment made against them by the Son of God. The opening pattern is the same, declaring their impending judgment and labelling them as pretenders: as hypocrites.

The reference to extensive travel might be exaggeration for effect—hyperbole—rather than an indication that the Pharisees went to foreign territory to seek converts. Scribes and Pharisees made extensive efforts to create “proselytes.” These are converts from one religious conviction to another. Some scholars and historians understand this to be a literal form of missionary work in which the Pharisees attempted to convert non-Jews to religious Judaism.

Some interpreters believe Jesus is referring to efforts by the scribes and Pharisees to win over current believers in Judaism. These might have been Gentiles who already believed in the God of Israel. The goal would have been to convince such people of their narrow views of the law, along with their teachings about the extra rules and regulations they required.

In either case, Jesus does not condemn the effort to win converts. He condemns what they are being won to: a belief system built around human regulations and a rejection of Jesus as the Messiah. These hypocritical religious leaders were redirecting people onto a path leading to hell, rather than to God and heaven. Those converted were likely to follow the wrong teachings of the Pharisees even more closely than the Pharisees did themselves!

Verse 16 “Woe to you, blind guides, who say, ‘If anyone swears by the temple, it is nothing, but if anyone swears by the gold of the temple, he is bound by his oath.’

Jesus continues His condemnation of Israel’s religious leaders, specifically the groups known as the scribes and the Pharisees. These were the primary self-professed teachers of Jewish law and spirituality. As the judge ordained by God (John 5:22), Jesus is pronouncing a series of “woes” against them. He now comes to the third such condemnation.

Highlighting their hypocrisy (Matthew 13:13) and false teaching (Matthew 23:15), Jesus repeats His criticism of these men as blind guides (Matthew 15:12–14; John 9:39–41). These religious leaders cannot hope to lead anyone to the correct conclusions since they can’t see the truth themselves.

The specific example Christ gives of this spiritual blindness involves the taking of oaths in binding agreements. Swearing oaths was deeply built into the culture of this time, though it’s not a practice most modern people understand. Under the ancient understanding, the responsibility of an oath was directly related to the power or sacredness of the object—or person—by which the oath was taken. During this period, the Israelites were not allowed to swear oaths on God Himself or even to speak the name of God directly. Instead, they would swear oaths by objects closely connected to God in some way, such as His throne, or the temple, or the altar.

Wallowing in legalism and loopholes, the Pharisees had apparently devised a system separating objects which would “truly” bind someone to their promise from objects not significant enough to require one to keep their word. This allowed a crafty person to swear an oath by something non-binding, leaving room to be deceptive about doing as they said. Jesus’ example is one of those distinctions: If someone swears by the temple, it was not a meaningful oath, but if someone swore by the gold of the temple, he or she was bound to do what was agreed to.

Jesus has already condemned the practice of taking oaths to lend weight to one’s word. During the Sermon on the Mount, He declared such tacked-on promises as unnecessary and as coming from evil. Instead, He insisted that people simply say “yes” and “no” and then do what they said (Matthew 5:33–37).

In these verses, the immediate criticism is how the Pharisees wrongly assign value according to worldly standards, not the standards of God.

Verse 17 You blind fools! For which is greater, the gold or the temple that has made the gold sacred?

Israel’s religious leaders are being condemned by Christ for the practice of using deceptive, layered “oaths” when making promises. As part of that error, these men suggested an oath made on some things related to God were not binding, while oaths made on other things were legitimate. He began with their position that an oath made on the temple is not binding, but an oath made on the gold in the temple is binding (Matthew 23:16).

Jesus now calls them blind fools (Matthew 15:12–14; John 9:39–41) for inventing these distinctions. Asking a rhetorical question, Jesus distinguishes between the gold and that which would make the gold sacred? Do the Pharisees think the gold is more valuable because it is worth more earthly money, or do they see the gold as sacred because it is in the temple? If it’s the latter, that should make the temple itself far more valuable. Jesus condemns their valuation of gold and of the temple.

At the same time, Jesus is repeating an earlier criticism, condemning the practice of offering extra promises on top of one’s sincere word. In this case, the Pharisees even taught that one such oath should be binding, while others were not. Making that distinction could only encourage taking meaningless oaths—a premeditated intent to break one’s word. As Jesus taught in the Sermon on the Mount, the proper thing is to give any promise in simple terms and then keep it, no extra guarantees needed (Matthew 5:33–37).

Verse 18 And you say, ‘If anyone swears by the altar, it is nothing, but if anyone swears by the gift that is on the altar, he is bound by his oath.’

Jesus is revealing the selfish motives and foolishness of the scribes and Pharisees in creating categories of oaths. He has already said that they distinguish between swearing by the temple and swearing by the gold that is in the temple. According to these religious leaders, making a vow on the gold creates a binding agreement, but doing so on the temple alone means nothing (Matthew 23:16–17).

The scribes and Pharisees have made a similar rule about swearing by the altar versus by the sacrifice given on the altar. As they would have it, swearing by the gift is binding, but swearing by the altar itself means nothing. This complicated system seems to have grown from a restriction on swearing on or by God Himself. Religious Jews at this time likely did not even say the name for God. Instead, they began to swear by things related to God when making oaths.

While adding extra “certification” to a promise is bad enough (Matthew 5:33–37), the suggestion that swearing by one thing as binding and another as non-binding reveals the Pharisees’ lack of understanding about the nature of God and what it means to swear an oath. In this way, they are “blind guides” and “blind fools.” They are leading those they teach away from what is wise and true (Matthew 23:13–15).

Verse 19 You blind men! For which is greater, the gift or the altar that makes the gift sacred?

Jesus has called the scribes and Pharisees blind guides (Matthew 23:16), blind fools (Matthew 23:17), and now simply calls them blind. Their ranking of some oaths as binding and others as non-binding shows their complete lack of understanding about what belongs to God and what it means to swear an oath (Matthew 23:13–15).

Using a traditional scheme of loopholes and technicalities, these religious leaders have declared that swearing by the gold of the temple or swearing by the sacrifice on an altar requires a person to keep their word. In contrast, they say, swearing by the temple or altar themselves is somehow non-binding. Jesus has pointed out that the temple that makes the gold sacred, just as the altar makes the sacrifice sacred. The scribes and Pharisees, of all people, should understand that all these things come from God and belong to God. These supposedly learned men don’t have any basis to declare one sacred and another not.

While not stated directly, this “woe” also underscores Jesus’ prior criticism of using oaths to enhance a promise. Why encourage anyone to take an oath, to swear by something sacred, for any reason? Why not just teach people to keep their plain word when they say “yes” or “no?” Anything more than that, as Jesus taught in the Sermon on the Mount, comes from evil (Matthew 5:33–37).

Verse 20 So whoever swears by the altar swears by it and by everything on it.

When people swear an oath, they are making a binding agreement to do what they say they will do. It is binding in the sense that both parties are held to their agreement according to the worthiness of what they swear on. That’s why some informal modern oaths, at least in the English language, have included “swearing on your mother’s life” or “swearing on a stack of Bibles.” These were thought to be the most solemn and valuable things to which a person could attach such an agreement.

Religious leaders of Jesus’ era, such as the scribes and Pharisees, taught the people of Israel to swear oaths on sacred things, like the gold in the temple or the gift on the altar. But they taught them not to swear on the temple or the altar themselves, as if some oaths were more binding than others. Jesus taught the people not to swear oaths, at all. Instead, they should simply be known for their integrity: to do what they say they will do (Matthew 5:33–37).

The point Christ makes in this criticism is not that there really are different levels of oaths. Rather, it’s that it’s absurd to separate one sacred thing from another. To swear by the altar of God in the temple is to swear by whatever is on the altar. The altar makes the gift or sacrifice sacred, because the one the gift is being offered to is holy. The Pharisees’ teaching fits the caricature of a “blind guide” (Matthew 23:16) leading people in bizarre directions (Matthew 23:15).

Verse 21 And whoever swears by the temple swears by it and by him who dwells in it.

Jesus continues to show just how foolish the teaching of the Pharisees is when it comes to the issue of swearing oaths to create binding agreements. It’s more than merely unwise: Jesus has declared “woe” upon them in judgment for leading the people of Israel astray in this way (Matthew 23:15–20).

Swearing by the temple of God amounts to the same as swearing by God Himself, since He “lives” in the temple. The Pharisees had declared that swearing by the temple was meaningless. Jesus is showing that swearing by the temple would be the same as swearing by God Himself. No oath could be more binding, or more dangerous for the one making it.

It’s important to understand that Jesus is not teaching people to swear by the temple. He has taught people not to use such “added on” enhancements to their promises, at all. Instead, Christ taught His followers to let their “yes” or “no” stand on its own (Matthew 5:33–37). What Jesus does here is prove that the scribes and Pharisees have neither a spiritual nor a logical basis for their teaching on oaths.

Verse 22 And whoever swears by heaven swears by the throne of God and by him who sits upon it.

During this passage, Jesus has warned of judgment coming upon the scribes and Pharisees for foolish teachings about taking oaths. The danger of taking an oath on the God of heaven is that if a person is unable or unwilling to keep the oath, they will be breaking their word to God. Instead, Jesus has taught that people should simply say “yes” or “no” and then do it (Matthew 5:33–37). Adding “enhancements” to a promise suggests a faulty view of what it means to be trustworthy.

Traditional teachers of that era, however, used a system in which a person might be able to swear an oath by something that is sacred without directly swearing by God Himself. They have told the people to swear by the gold of the temple, or by the gift on the altar, without swearing by the temple or alter themselves. Jesus has shown this is ridiculous. You cannot separate the sacredness of altar from the sacrifice or the temple from the gold inside of it.

In the end, everything is God’s. Everything a person might swear by, in truth, leads back to God. To swear an oath of any kind by anything connected to God in any way is to swear an oath to God, making the one who swears it vulnerable to God’s judgment for breaking it.

Jesus now returns to a point that may have prompted the Pharisees to make these rules in the first place. Apparently, some had decided that swearing by God’s throne was acceptable, while swearing by God was not. Others thought that maybe swearing by heaven would be better than swearing by God’s throne. Jesus shows that swearing by any of them is the same as swearing by God. To teach that these things are separate from Him is foolishness (Matthew 23:16–21).

Verse 23 “Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cumin, and have neglected the weightier matters of the law: justice and mercy and faithfulness. These you ought to have done, without neglecting the others.

Jesus launches into the fourth or His seven “woes” against Israel’s religious leaders, the scribes and Pharisees. These are more than just a performance review, or a debate-style attack against Jesus’ opponents. These are pronouncements of judgment. They come from the Son of God against those entrusted by God with the religious and spiritual leadership of His people.

After calling them hypocrites once again (Matthew 23:13, 15), Jesus describes what may be the heart of the Pharisees’ problem when it comes to their practice of Judaism. Over time, Jewish leaders developed a system of intricate details meant to “protect” people from accidentally breaking one of God’s commandments. Men like scribes and Pharisees pour intense energy into obeying the smallest details of these traditional, manmade rules. At the same time, they are missing the point of the actual God-given laws which inspired their traditions. They are blind to the heart of God for His people.

The Israelites were commanded to tithe—give ten percent of—certain specific crops. This included oil, grain, and wine (Deuteronomy 14:22–29). Leviticus 27:30–32 goes a bit further, specifying seed of the land, fruit from trees, and animals from the herds. The Pharisees had chosen to apply this requirement to even the tiniest of the garden plants, including mint, dill, and cumin. Jesus does not condemn their choice. In fact, He says that aspect of their obedience is legitimate. At the same time, it is an example of the exacting lengths the Pharisees went to—and imposed on the people—to try to be legalistically perfect.

In focusing on these details, the Pharisees became insensitive to the greater point of those laws. Obedience was important, of course, but just as important is to know the purpose the regulations given by God. Only by knowing the purpose can a person rightly judge (John 7:24) how to apply those laws. The Lord intended for His people to live in justice, mercy, and faithfulness. Without those end goals, all the rules became mere religious exercise instead of a way to accomplish the will of God for His people.

Verse 24 You blind guides, straining out a gnat and swallowing a camel!

This passage illustrates the central problem of the scribes and Pharisees, both in their practice of Judaism and how they imposed it on the people. They went to the trouble to give the required ten percent of the smallest of the garden “crops,” even tiny herbs. That was fine, but they obsessed over these details, while missing the big reasons behind God’s law for His people: justice, mercy, and faithfulness (Matthew 23:23–24).

In other words, these spiritual leaders did not interpret the law to the people in a way that emphasized what God really cared about. To use a common English expression, they “missed the forest for the trees:” they forgot that details are meant to form a larger picture. They focused on wooden, legalistic religious performance in a way that ultimately only served their own pride, power, and glory. Jesus once again calls them blind guides (Matthew 23:16–17), meaning they have no understanding of where they are leading God’s people.

This obsession with legalistic details is compared to someone who uses a screen to keep insects out of their drink, while failing to notice a massive animal floating in there. It’s a humorous and devastating line. Both gnats and camels were unclean for the Israelites to eat. To avoid even accidentally eating something ritually unclean, Pharisees would use cloth to strain their drink. Like tithing from their herb crop, this was exacting work performed to be religiously perfect.

The scribes and Pharisees could not—or would not—see they were missing the much more important reasons behind God’s regulations for His people. Obeying specific commands is important, but details are not meant to override the broader message being given by God.

Verse 25 “Woe to you, scribes and Pharisees, hypocrites! For you clean the outside of the cup and the plate, but inside they are full of greed and self-indulgence.

Jesus continues His devastating description of the practices of the scribes and Pharisees as Israel’s religious leaders (Matthew 23:13–24). This is the fifth of the seven “woes” in Matthew account of this confrontation. Jesus again calls these men “hypocrites” (Matthew 23:13, 15, 23), which is from a Greek term literally referring to stage actors. They are pretenders who say one thing but do something else.

This new criticism comes in the form of a powerful word picture. Jesus captures exactly how the Pharisees live and lead God’s people. Their emphasis on legalism, appearances, and worldly honor is like washing the outside of the cups and plates instead of the insides. No matter how clean they might look, these utensils would be filthy in all the ways that matter. The only reason someone would do such a foolish thing would be if they only cared about how they looked and cared little for actual cleanliness. The Pharisees wanted everyone to see them as clean, religiously perfect, and the most spiritual men of all.

Like dishes only washed on the outside, the insides of these religious pretenders were full of greed and self-indulgence. The Pharisees and scribes used details of the law as a cover up for their sin. They were not practicing it in humility, seeking to reject their own sinful attitudes and ideas. In short, their religion served themselves. It sought to satisfy their own desires as much as possible without ruining their prestigious reputations.

Verse 26 You blind Pharisee! First clean the inside of the cup and the plate, that the outside also may be clean.

Yet again, Jesus calls the Pharisees blind (Matthew 23:16–17, 19). He has condemned them for putting on a show of religiosity while having selfish hearts. This is as absurd and disgusting as cleaning the outside of cups and plates while the insides are filthy. Jesus’ continual description of them as “blind” reveals they lacked even the ability to see the truth for what it was. They did not have the capacity to lead the people well because they refused to see what was right in front of them (John 5:39–40).

Instead of trying to appear pious while letting selfishness run unchecked in their hearts, they should clean themselves up on the inside. A clean-minded person will naturally act in clean ways (Matthew 15:11). If the Pharisees sincerely rejected greedy attitudes and appetites, they would naturally become known as selfless, servant-hearted men. Instead, they pretended to be holy while continuing to serve themselves in every way they could get away with.

The imagery of something pretty on the outside, but repugnant on the inside, will be given an even more dramatic use in the next verses (Matthew 23:27).

Verse 27 “Woe to you, scribes and Pharisees, hypocrites! For you are like whitewashed tombs, which outwardly appear beautiful, but within are full of dead people ‘s bones and all uncleanness.

Jesus continues to pronounce judgment on Israel’s religious leaders: the scribes and the Pharisees. In this next “woe” statement, He describes them as tombs that have been painted over. Under Old Testament law, anyone who came into contact with a dead body became ceremonially unclean (Numbers 19:11). The Pharisees avoided this at all costs.

Despite outward appearances, these hypocrites (Matthew 23:13, 15, 23, 25) have hearts which are disgusting. In this era, the caves or rock piles used for tombs were regularly painted or washed white with lime. Some had artful memorials built over the graves. Outwardly, they look clean and neat. And yet, beneath those clean, attractive exteriors were rotting corpses. Beautiful though they may have been, they were full of death and as unclean as anything a faithful Jew could imagine.

In the same way, the Pharisees appeared to be the most unstained of all the Israelites. Inwardly, though, Jesus describes them as full of death. In this way, they are like the cups Jesus described in the previous “woe”–clean on the outside and filthy inside (Mathew 23:26).

Verse 28 So you also outwardly appear righteous to others, but within you are full of hypocrisy and lawlessness.

Burial sites that are painted or covered in artwork are only beautiful on the outside. Under the surface, they’re literally full of death. This is the analogy Jesus is using for the religious leaders of Israel: the scribes and Pharisees. Their legalism and reputation give the appearance of life, but underneath it all is spiritual death (Matthew 23:13–27). Now the Lord drives His point home.

Outwardly, the Pharisees and scribes appear righteous. They seem to be keeping all the commands of Scripture, and the added rules and regulations they have imposed on the people. Inwardly, though, they are liars and rebels (Luke 12:1). Jesus again brings up the idea of “hypocrisy,” which is derived from the Greek word for stage actors. No matter the scribes’ and Pharisees’ commitment to the public-facing rules of the law, their hearts remain unchanged. The most seemingly lawful of Israel’s people are deeply unlawful in the place that matters most, their inner lives.

Jesus has called them hypocrites repeatedly (Matthew 23:13, 15, 23, 25, 27). He now emphasizes they are full of this hypocrisy. It’s coming from the inside out (Matthew 15:11, 18).

Verse 29 “Woe to you, scribes and Pharisees, hypocrites! For you build the tombs of the prophets and decorate the monuments of the righteous,

Jesus delivers another resounding condemnation or “woe” against the Pharisees and scribes. For their hard-hearted rebellion against God, they become participants in the same crimes as their forefathers. Israel’s religious leaders of old persecuted and killed the prophets sent by God with hard messages for the people of Israel (Acts 7:52; Matthew 23:27–28). Those prior generations openly rejected God’s messengers.

The Pharisees and scribes of Jesus’ generation are just as guilty, even though they build memorials and monuments to those same prophets tormented by their forefathers. Jesus is offering yet another example of hypocrisy: presenting one picture of themselves when the opposite was true. In this passage, Jesus has shown how these religious leaders focus on appearances, and legalism, while missing or contradicting the actual intent of God (Matthew 23:23–24).

Verse 30 saying, ‘If we had lived in the days of our fathers, we would not have taken part with them in shedding the blood of the prophets.’

It’s extremely common for people to look at prior generations and claim “I would not have made that mistake.” This applies to cultural as well as religious ideas. Many Christians believe if they had been born and raised in the era of Jesus Christ, they would have seen the truth, leaving behind the entire religious system of their day to follow Jesus. In this way, we deny that human nature is to be as sinful and blind as those who rejected Jesus in the first place. While it’s possible we might have been among those who believed, it’s also possible we’d have been participants in those same sins.

The Pharisees and scribes were guilty of this very failure; they did not see their own rejection of God’s messengers. While their rebellion was well disguised (Matthew 23:27), they were actively repeating the disobedient error of their ancestors. They are sure that if they had lived in the days of their own forefathers, they would not have rejected God’s prophets and joined in killing them.

Those present to hear Jesus say these words, however, actively rejected the prophet John the Baptist. He came to point the world to Jesus and the Messiah (Matthew 21:23–27). Within the week, these same groups—the scribes and Pharisees—would participate in condemning Jesus, the Son of God, and seeing Him executed by the Romans at their urging (Matthew 16:21; 27:24–26). Their sin is every bit as great as the sins of their ancestors who rejected and killed the prophets sent to Israel by God.

Verse 31 Thus you witness against yourselves that you are sons of those who murdered the prophets.

Jesus is exposing yet another form of hypocrisy practiced by the scribes and Pharisees. The term “hypocrite” is transliterated from the Greek word hipokritēs, which literally meant stage actors. Those who say one thing, but live something else, are pretenders. Christ has already criticized these men for claiming to honor God, when their actions are legalism and self-honoring (Matthew 23:1–7).

The next form of pretense comes in how these men speak about God’s messengers from prior generations. The Pharisees and scribes claimed to honor and celebrate Israel’s prophets of old. They believed they would never have joined those who rejected and killed these messengers sent from God to His people Israel. Jesus refutes their arrogance with a rhetorical point which can be hard for modern readers to follow.

As Christ frames it, when the scribes and Pharisees admit their forefathers persecuted God’s messengers, they put themselves into the same category of guilt. In that culture, society often placed a sense of guilt on the children of criminals. Jesus points out that these leaders are, by their own admission, the sons of the killers of God’s messengers. In a rhetorical sense—by the standards of the day—these men are identifying themselves with enemies of the Lord.

At the same time, Jesus knows that these men are “spiritually” the sons of those murderous ancestors. Their attitudes towards the Son of God prove their spiritual condition (John 8:43–44). The same religious leaders who claim they would have listened to ancient prophets have already rejected John the Baptist (Matthew 23:21–27). Even now they are plotting to have Jesus murdered (John 11:53; Mark 3:6; Luke 22:2).

Verse 32 Fill up, then, the measure of your fathers.

The Pharisees and scribes of Christ’s day are the literal sons of those who persecuted God’s messengers in the past (Acts 7:52). They are also the spiritual sons of Satan: those who reject and defy God and His Son (John 8:43–44). Their own claims prove this (Matthew 23:31), since they have rejected John the Baptist (Matthew 23:21–27) and are plotting to have Jesus killed (John 11:53; Mark 3:6; Luke 22:2).

Christ’s biting command here can be interpreted in two simultaneous ways. Since these men frequently make claims to their heritage (Matthew 3:9), Jesus is harshly telling them to follow through fully: to live up to the example of their predecessors who killed the prophets. At the same time, He is dismissing them to continue in sin until God’s wrath has built up in anticipation of judgment. In either sense, these men are close to the “tipping point.” Christ’s words here are both condemnation and contempt.

Verse 33 You serpents, you brood of vipers, how are you to escape being sentenced to hell?

The idea that Israel’s most righteous people, the religious leaders known as the scribes and Pharisees, might be damned by God would have been mind-blowing to everyone in Israel. This would have been especially true for those religious leaders themselves. Yet Christ does not hesitate in His ongoing condemnation of them (Matthew 23:13–32). He even calls them harsh names: serpents and a brood of vipers. Snakes served as a symbol of evil throughout Israel’s history (Matthew 3:7; 12:34).

The question asked here is rhetorical: Jesus is not “asking” so much as He is declaring that these men are doomed. This is not mere argument and debate. Jesus is the Judge and the King (John 5:26–27). The Pharisees do not realize it, but they stand condemned before God already, as they physically stand before the Messiah. Instead of bowing before Him in humility to request mercy, they are plotting to kill Him (John 11:53; Mark 3:6; Luke 22:2).

Jesus spoke often of hell and eternal judgment for those who rejected God’s Savior and Son, the Messiah, even among God’s chosen people (Matthew 22:13; 23:15).

Verse 34 Therefore I send you prophets and wise men and scribes, some of whom you will kill and crucify, and some you will flog in your synagogues and persecute from town to town,

Jesus has declared the Pharisees and scribes of His day as equal in guilt to their forefathers. Those predecessors killed God’s prophets of old (Acts 7:52). They have repeated the pattern of their fathers in rejecting John the Baptist’s work and message and in rejecting and plotting to kill Jesus (Mathew 23:21–27; John 11:53; Mark 3:6; Luke 22:2). Far more important than their heritage, these men are proving their spiritual family is that of Satan (John 8:43–44).

After soundly condemning these hypocritical leaders (Matthew 23:13–28), Jesus speaks about the future. Sadly, this is exactly what happens to the apostles and evangelists of Christ during the years of the early church. What He describes here will begin immediately after His death, resurrection from the dead, and return to heaven (John 16:1–4). They are persecuted, jailed, and killed by the Jewish religious leaders working in conjunction with the Roman Empire. In doing this, Jesus establishes that they will be repeating exactly the pattern of their ancestors, who killed the prophets whom God sent to warn Israel of His coming judgment.

God’s plan will include sending more messengers, summarized by Christ here as “prophets and wise men and scribes.” This provides further opportunity for the world to hear the gospel (Matthew 23:19). Also, it provides further evidence against those who reject God’s truth. The scribes and Pharisees of Jesus’ era will persecute and murder many of these future messengers. They will even pursue them when they try to flee persecution (Acts 8:1–3).

Verse 35 so that on you may come all the righteous blood shed on earth, from the blood of righteous Abel to the blood of Zechariah the son of Barachiah, whom you murdered between the sanctuary and the altar.

God’s wrath is something which can be stored up until sin reaches a tipping point; then God begins to pour out judgment (Matthew 23:29–34). The Pharisees and scribes of Jesus’ era will reach that tipping point with their own sinful actions. As predicted by Christ, these men will continue to murder and oppress those who believe in Jesus (Acts 8:1–3). In a chilling metaphor, Jesus speaks of that generation experiencing a reckoning for thousands of years of sin.

The “righteous” ones listed here are those who followed God in humility and sincerity. Abel was the victim of humanity’s first murder, killed by his brother, Cain, in a jealous rage (Genesis 4:4–8). Zechariah’s murder, as an act against God’s messenger (2 Chronicles 24:20–22), is also connected to the sin of these scribes and Pharisees. These two incidents occur early in the book of Genesis and late in the book of 2 Chronicles. In the Jewish Scriptures of that time, those were considered the first and last books, respectively. In a literary sense, this implies all prophets and messengers martyred in the Old Testament.

Skeptics sometimes note that Jesus mentions Barachiah as Zechariah’s father. The name given for the father of a man named Zechariah in 2 Chronicles chapter 24 is Jehoiada. Jesus might possibly be referring to the prophet mentioned in Zechariah 1:1. Or, the Zechariah of 2 Chronicles was the descendant of a man named Barachiah, not necessarily his immediate son.

It is interesting that the Zechariah described in 2 Chronicles 24:20–22 said, “May the Lord see and avenge!” as he was dying. Jesus predicts that very vengeance will be delivered upon the scribes and Pharisees of His own day.

Verse 36 Truly, I say to you, all these things will come upon this generation.

Jesus has been clearly and harshly pronouncing God’s condemnation and coming judgment on Israel’s religious leaders: the scribes and Pharisees (Matthew 23:13–32). Most recently, Christ said that God would deliver judgment for all the murders of godly servants from Abel (Genesis 4:4–8) to Zechariah (2 Chronicles 24:20–22) on these modern leaders of Israel.

In this statement, Jesus takes the pronouncement of judgment even further. This coming judgment of God for these sinful actions and murder will come upon this generation. God’s angry retribution for the rejection of Jesus and God’s messengers will not be limited to Israel’s religious leaders. All of Israel will be judged: both the leaders and those who willingly follow them. Many scholars believe Jesus’ prediction of this judgment came to pass, at least in part, during the devastating Roman destruction of Jerusalem in AD 70.

Context Summary
Matthew 23:13–36 contains seven layers of condemnation, from Jesus, towards the religious leaders of His era. Each of these is introduced with the word “woe,” which is an exclamation like “oh!” or “alas!” Pronouncing God’s judgment on these men, He repeatedly describes them as “blind” and “hypocrites.” Convincing others of their views only adds victims to hell. They follow the letters of manmade law to the tiniest detail but miss the real meaning of Scripture: God’s heart for justice, mercy, and faithfulness. Their outer appearance of righteousness hides inner lives full of greed, self-indulgence, hypocrisy, and lawlessness. Those in Jesus’ generation will pay for many of the righteous people unjustly killed in the past.

Verse 37 “O Jerusalem, Jerusalem, the city that kills the prophets and stones those who are sent to it! How often would I have gathered your children together as a hen gathers her brood under her wings, and you were not willing!

So far as the gospel of Matthew is concerned, these are the last words Jesus will speak to Jerusalem in a public setting. He has more yet to teach, and the two chapters will contain extensive records of those words. This, however, is the point where Jesus’ public ministry ends (Matthew 23:39). Prior to this, Jesus has been condemning Israel’s failed religious leadership (Matthew 23:1–3). Those words were delivered with a cutting, direct mood. Here, Christ’s words are significantly more mournful. Looking ahead to the disaster that will come on the city, Jesus speaks with a tender and longing tone.

Despite being the chief city of God’s chosen people, Jerusalem has earned a sad legacy over the generations (Acts 7:52). This city of David has become known as the city that kills prophets and stones the messengers God sends to her. That legacy will be emphasized eternally within the week as Jesus Himself is condemned and killed in Jerusalem (Matthew 26:1–5).

Jesus describes the role He would have rather held in relationship to the city and the people of Israel. Speaking from the perspective of God, as a member of the Trinity, Jesus notes how often He would have stepped in to protect Jerusalem and her children. The symbolism here is unique in Scripture and carries an almost maternal sense. Jesus, the Son of God, describes His heart motive to protect His people.

Of course, since God is omnipotent, that raises the question of why God did not, in fact, offer that level of protection. Why did they suffer so much judgment and death? Why will the city be exposed to the destruction yet to come (Matthew 24:1–2)? The answer is not complex, though it can be hard to accept: the people were not willing to receive His protection. They rejected God, and His messengers, and His message (John 5:39–40). And so, judgment fell, and would soon fall again.

Verse 38 See, your house is left to you desolate.

Mournfully, Jesus declared that He would have protected the people of Jerusalem, much as a hen would shield chicks under her wings (Matthew 23:37). Jerusalem, through her own people and their religious leaders (Matthew 23:1–3), rejected the protection of the Lord and has now rejected Jesus as the Messiah. That rejection will soon result in Jesus being unfairly condemned and executed (Matthew 26:1–5).

One consequence of this tragic rejection (John 5:39–40) is that God’s protection will be entirely removed. Like a building abandoned and empty, there will be nothing left able to prevent disaster. These words echo those of the prophet Jeremiah (Jeremiah 12:7), speaking about Israel’s prior experiences with judgment. They also point forward to the dire prediction Christ will make in the opening verses of the next chapter: “There will not be left here one stone upon another that will not be thrown down (Matthew 24:2).” This seems to be a reference to the huge temple in Jerusalem, perhaps a parallel meaning for the word “house” in this verse.

History records that within a few decades of Jesus’ death and resurrection, tensions between Israel and Rome resulted in disaster. The Roman army was set loose on the city in AD 70, annihilating much of the population and literally tearing the temple apart brick-for-brick.

Verse 39 For I tell you, you will not see me again, until you say, ‘Blessed is he who comes in the name of the Lord.’”

In this chapter, Jesus has warned of impending judgment on Israel’s religious leaders (Matthew 23:1–3) and on her people (Matthew 23:38). Speaking from His perspective as God, and looking into Israel’s past, Christ mourned Jerusalem’s rejection of Him (Matthew 23:37). Now, through the actions of their religious leaders, they have fully and officially rejected Him as the Messiah. Without His protection, Jerusalem and its temple will be left as vulnerable as an abandoned building, with no One to protect them.

In that context, Jesus says that He will not be there to protect Israel. Further, His public ministry is now complete. The people, in a public sense, will not see Him again until He returns as the conquering King (Revelation 19:11–15). He cites Psalm 118: “Blessed is he who comes in the name of the LORD (Psalm 118:26).” When Jesus comes to Israel again, He will not come as a sacrificial Savior (Matthew 16:21), but as the Judge (Hebrews 9:28). At that time, the people of Israel will finally acknowledge His true position as their King.

Context Summary
Matthew 23:37–39 contains Jesus’ cry of mourning over Jerusalem’s unfaithfulness and impending ruin. He describes a devastating legacy of killing prophets and stoning God’s messengers. Christ speaks from His divine perspective as a member of the Trinity. He expresses the longing God shows, in both the Old and New Testaments, to protect Jerusalem’s children. Yet they have rejected Him. Now He will withdraw, and God’s judgment will come. Jesus’ public ministry in Jerusalem is now over: the city at large will not see Him again until they are ready to apply the words of Psalm 118: “Blessed is he who comes in the name of the Lord!”

Chapter Summary
After thoroughly dismantling scribes, Pharisees, and Sadducees in debate, Jesus even more thoroughly condemns these religious leaders for their religious hypocrisy. They do all their religious acts and works to be seen and approved of by other people. Jesus pronounces God’s judgment on the scribes and Pharisees in a series of seven “woe to you” statements. He repeatedly calls them “blind” and “hypocrites.” He concludes with a lament for Jerusalem and her children who rejected His protection. God’s judgment is coming.