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Woe, Woe, Whoa!

Jesus talks to the crowd about the Pharisees.

Written by David Steltz on .



‌We are getting right back into Matthew today, after a quick shift last week to focus on Easter.

We’re in chapter twenty three of Matthew now, and the discourse we see here is situated after Jesus arrives in Jerusalem, and before the weekend of his arrest, execution, and resurrection.

‌That is, the week between Palm Sunday and Easter.

I believe we’ll be spending several more weeks of our time together here studying this one last week leading up to Passover. 

In these few chapters, Jesus drops some hard truths, and makes some piercing accusations. He passionately prophecies for repentance, shining a light on the hopelessness of a lost generation and the calamity which will befall it, while providing hope of redemption through the source of light: himself.


To make sure we read this in the right context, I want to quickly recap what’s led up to this section of teaching.

‌In Jerusalem’s Temple

‌After a long journey with his disciples, Jesus has finally arrived in Jerusalem. While he was received with a very warm welcome from the crowds, he is still very unpopular with the religious leaders and authorities.

Jesus soon made it clear that he was not in town to rub shoulders and gain favor with the elite, nor advance himself politically or financially. In fact, he caused quite a scene when he went straight to the temple and kicked out all the merchants from selling there, before settling in to teach.

Confrontations to Silence

‌And that’s where we are, that’s where we’ve been for the last few weeks of Matthew…in the temple, in Jerusalem, seeing Jesus teaching and interacting with the people around him. He’s dealing with questions of his authority, and tests design to trap him in his words, while also telling parables about the Kingdom of God and the Messiah.

We last left off with three confrontations; three conversations with Jesus, each beginning with a question from the Pharisees or Sadducees, attempting to catch Jesus in a scandal.

Of course, every one of those three conversations ends when Jesus replies with incredible wisdom and authority, completely astounding his listeners and attackers, until they have nothing left to say. 

Chapter 22 ends with the statement that after nobody could answer him, nobody dared ask him any more questions.

Woes of Judgment

Chapter 23 now launches us headlong into an uninhibited section of teaching - the last major stretch of teaching in Matthew, which will take us all the way through the end of chapter 25.

Passage (Matt 23)

‌And, beginning with today’s passage, a lot of the teaching to come is NOT heartwarming, nor is it meant to be. 

Although the message ultimately brings us to the wonderful good news of salvation through Christ, it also highlights the depravity which led us away from it in the first place. 

In traditional prophetic fashion, there is a strong thread of hope woven into a frightening patchwork of chaotic reality.

It’s a long passage, but I want us to read the whole chapter together, because it’s a kind of finale to his time spent teaching there in the temple.

Matthew 23 NLT
1 Then Jesus said to the crowds and to his disciples, 2 “The teachers of religious law and the Pharisees are the official interpreters of the law of Moses. 3 So practice and obey whatever they tell you, but don’t follow their example. For they don’t practice what they teach. 4 They crush people with unbearable religious demands and never lift a finger to ease the burden. 5 “Everything they do is for show. On their arms they wear extra wide prayer boxes with Scripture verses inside, and they wear robes with extra long tassels. 6 And they love to sit at the head table at banquets and in the seats of honor in the synagogues. 7 They love to receive respectful greetings as they walk in the marketplaces, and to be called ‘Rabbi.’ 8 “Don’t let anyone call you ‘Rabbi,’ for you have only one teacher, and all of you are equal as brothers and sisters. 9 And don’t address anyone here on earth as ‘Father,’ for only God in heaven is your Father. 10 And don’t let anyone call you ‘Teacher,’ for you have only one teacher, the Messiah. 11 The greatest among you must be a servant. 12 But those who exalt themselves will be humbled, and those who humble themselves will be exalted. 13 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you shut the door of the Kingdom of Heaven in people’s faces. You won’t go in yourselves, and you don’t let others enter either. 15 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you cross land and sea to make one convert, and then you turn that person into twice the child of hell you yourselves are! 16 “Blind guides! What sorrow awaits you! For you say that it means nothing to swear ‘by God’s Temple,’ but that it is binding to swear ‘by the gold in the Temple.’ 17 Blind fools! Which is more important—the gold or the Temple that makes the gold sacred? 18 And you say that to swear ‘by the altar’ is not binding, but to swear ‘by the gifts on the altar’ is binding. 19 How blind! For which is more important—the gift on the altar or the altar that makes the gift sacred? 20 When you swear ‘by the altar,’ you are swearing by it and by everything on it. 21 And when you swear ‘by the Temple,’ you are swearing by it and by God, who lives in it. 22 And when you swear ‘by heaven,’ you are swearing by the throne of God and by God, who sits on the throne. 23 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you are careful to tithe even the tiniest income from your herb gardens, but you ignore the more important aspects of the law—justice, mercy, and faith. You should tithe, yes, but do not neglect the more important things. 24 Blind guides! You strain your water so you won’t accidentally swallow a gnat, but you swallow a camel! 25 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you are so careful to clean the outside of the cup and the dish, but inside you are filthy—full of greed and self-indulgence! 26 You blind Pharisee! First wash the inside of the cup and the dish, and then the outside will become clean, too. 27 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you are like whitewashed tombs—beautiful on the outside but filled on the inside with dead people’s bones and all sorts of impurity. 28 Outwardly you look like righteous people, but inwardly your hearts are filled with hypocrisy and lawlessness. 29 “What sorrow awaits you teachers of religious law and you Pharisees. Hypocrites! For you build tombs for the prophets your ancestors killed, and you decorate the monuments of the godly people your ancestors destroyed. 30 Then you say, ‘If we had lived in the days of our ancestors, we would never have joined them in killing the prophets.’ 31 “But in saying that, you testify against yourselves that you are indeed the descendants of those who murdered the prophets. 32 Go ahead and finish what your ancestors started. 33 Snakes! Sons of vipers! How will you escape the judgment of hell? 34 “Therefore, I am sending you prophets and wise men and teachers of religious law. But you will kill some by crucifixion, and you will flog others with whips in your synagogues, chasing them from city to city. 35 As a result, you will be held responsible for the murder of all godly people of all time—from the murder of righteous Abel to the murder of Zechariah son of Barachiah, whom you killed in the Temple between the sanctuary and the altar. 36 I tell you the truth, this judgment will fall on this very generation. 37 “O Jerusalem, Jerusalem, the city that kills the prophets and stones God’s messengers! How often I have wanted to gather your children together as a hen protects her chicks beneath her wings, but you wouldn’t let me. 38 And now, look, your house is abandoned and desolate. 39 For I tell you this, you will never see me again until you say, ‘Blessings on the one who comes in the name of the Lord!’”

‌His Addressees (vs 1)

‌Let’s start with verse 1, which simply tells us who Jesus is now addressing. Whereas in the previous passage, Jesus was conversing with the Pharisees and others, he is now speaking to the crowds, and to his disciples.

And he does talk about the Pharisees, whether or not they are still there to hear it, he talks about them, but not to them. He’s bold, and direct, and it’s genuinely for the sake of his listeners. 

‌Bear in mind, that as has been the case throughout the whole story of Jesus’s arrival in Jerusalem, everything Jesus does and says comes out of a deep love for his people, born out of unity with the Father.

This final discourse is going to be pretty heavy-handed at times!

It starts with Jesus speaking out against the Pharisees in the beginning and includes judgment against Jerusalem as a whole by the end.

But the goal of Jesus saying these things was not simply to besmirch the reputation of the pharisees, or to publicly shame and humiliate them out of spite.

He turns to his disciples, and anyone else who will listen, to warn them not to draw their example from that of their hypocritical leaders, but rather to follow him instead.

‌Scribes & Pharisees (vs 2-8)

‌He warns them, and says NOT that they should ignore what the Scribes and Pharisees teach, but rather that they should ignore the example the Pharisees set.

In fact, he starts off by acknowledging that they are very well-versed in the Torah, that they are filled with head knowledge…valuable knowledge that should still be listened to.

But warns that their actual lives, their lifestyle and attitude, their treatment of others, none of that was a good demonstration of understanding the Torah, or of a person who spends time in close fellowship with Yahweh, allowing his spirit to transform them.

Rather, they are like actors, pretending to be something they are not…corrupt and rotting faces underneath a mask of piety and righteousness. Hypocrites.

Jesus literally says “do as they say, but not as they do.”

He criticizes their strict and burdensome teachings…rules they imposed in the name of following God’s law, but missing the intent of the law while doing so.

He describes them as pompous, vain, and puffed up. Concerned with being seen, being impressive, and feeling important. Of being held in high esteem and treated with respect.

In a way, they were seeking a form of worship from others…worship of their status, their divine authority and power, and of their unsurpassed knowledge and righteousness.

Verse 5 describes the physical accessories they would wear, to literally show off how godly and important they were. 

I guess it makes sense…everyone knows that you get extra godliness points for attending a church service if you do so while carrying a bible!

The specific traditions they had may seem foreign to us, but the underlying trap, the temptation that any of us can face, is to assign more value and priority to outward, and self-centered performances of worship rather than the genuine, personal, and God-centered expression of love and surrender. 

Siblings of No Rank (vs 7-10)

In verse 7, Jesus gives an example which is symptomatic of a deeper heart issue, and it’s how much they love being called “Rabbi” or “Teacher” by others.

At face value, the word “teacher” is simply descriptive and harmless, but in this context, it was used as a title of veneration, and pride.

It’s not that their position is not worthy of respect. In theory, what the scribes and pharisees do is incredibly important to the Jews, and worthy of honor and respect. But they had come to love the respect itself more than the underlying privilege of being able to study God’s word and share it with others.

‌Today, we don’t use the title “teacher” very often as a way to directly address someone, do we? 

Perhaps more relatable to “church” culture today would be the title of “Pastor.”

There’s certainly nothing wrong with that title; it’s used in the New Testament, that’s where we get it!

But there is certainly some baggage, some associations with that word, whether for some people it means putting anyone with that title of “Pastor” up on a pedestal, or for others associating all pastors with egotistical, perverted jerks.

In reality, pastors are the same as anyone else, in that we are all sinners in need of a savior, and have all been gifted and called in different ways to serve each other as brothers and sisters in the body of Christ.

We should all view each other with respect, as fellow image-bearers, and recognize everyone and what they do…whether it’s teaching, or cooking, or babysitting, or praying, or singing, or fixing cars…they all can and should be used for the edification and unification of the church. 

What we shouldn’t do is view any one person as being more holy, or latch on to any one teacher as being the one person you align yourself with, UNLESS that one person, that one teacher, is Jesus Christ himself. 

That’s what Jesus is getting at here, and Paul will get into the weeds with this later one, when people were aligning themselves wither with Peter or with Paul or with whoever it was that baptized them.

We have all been baptized into ONE body, one faith, one authority over all, and that’s the authority of Christ.

‌It’s good to learn from each other, and from those who went before us. For those of you in the Ephesians class, you’re getting to know one of my favorite teachers, Tim Mackie. I’ve learned so much from him over the years, and can relate really well to his teaching style. I’m so grateful for the ministry he helped start and for how much it’s helped me grow in my faith and understanding of scripture. 

However, I’m also not going to start calling myself a “Mackian” or “Bible Projectist!” Wouldn’t it be ridiculous if the people of NCF were divided between “Biolsians” and “Steltzists?” And yet, throughout church history, from the beginning, that has been the human tendency, the temptation to focus more on one teacher, one writer or theologian, one pastor, or evangelist, and putting all our stock in everything they say, while not ever going straight to the source ourselves, and letting the holy spirit teach us directly.

Now, I’m not saying you shouldn’t listen to me or Mike at all! Obviously, we believe God wants to use us and speak through us in sharing what he’s shown us in his word. But that doesn’t make us any more or less important than anyone else, and it doesn’t mean that we won’t ever make mistakes, or get something wrong, which is why you should always be checking what we say against Scripture, and even comparing with what other teachers have to say…there are many people much smarter than us who have lots to say, and we have unprecedented access to their wisdom, across the world and across history!

I do hope you can trust in our intentions, and generally find what we say to reliable, but we are not perfect. We don’t know everything.

When Jesus says “Don’t let anyone call you teacher.” and “Don’t call anyone on earth Father” he’s not literally banning the use of those words, nor is he suggesting that we be totally cynical and distrusting of anyone in a position of authority. The church is filled with diversely gifted people, including teachers, and Jesus isn’t negating that here.

He’s simply warning against the tendency that we have of glorifying our human teachers and mentors and relying on their example and testimony so much…building our faith on that one person, rather than Christ. Perhaps the gravest danger in that, is that if our faith is constructed around one person’s teaching, the moment we see them fail, or find an issue with their views, then our faith is at risk of collapsing completely. ‌

Exalted to Servants, Humble to Exalted. (vs 11-12)

In verses 11-12 Jesus makes a statement that, honestly, should sound pretty familiar by now, it’s not the first time he’s said something like it:

​Matthew 23:11–12 LSB
11 “But the greatest among you shall be your servant. 12 “And whoever exalts himself shall be humbled; and whoever humbles himself shall be exalted.

‌It’s that classic upside-down kingdom language we’ve come to expect from Jesus. Basically turning everyone’s expectations and preconceived notions on it’s head.

The pharisees were clearly exalting themselves, rather than exalting God, and helping others do the same. And the next few verses that follow are specific condemnations against the Pharisees and other religious teachers. 

Woes (vs 13-36)

‌You might see them referred to as “The Seven Woes.” There are seven different prophetic pronouncements of judgment aimed at these religious leaders. Instead of extolling their virtues, as they would be more accustomed to, he calls out their hypocrisy and lack of faith.

‌Let’s look at each one of these briefly.

‌1. Unholy Bouncers (13-14)

In verse 13, he says:

‌Matthew 23:13 LSB
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.

‌He’s accusing them of deterring people from the gates of Heaven, like some kind of unholy bouncers…they won’t go in themselves, and they’ll keep everyone else from getting in if they can.

In this case, Jesus IS the true door, the true gate, the path to life, eternal life in the kingdom of God. And they are trying to pull people away from him, from following him.

Beware of anyone who attempts to draw you away from Jesus or sow any seeds of distrust in him.

Verse 14?

‌That’s verse 13, what’s the next verse?

What comes after 13?

‌Well, it depends on your translation…some of you may have a verse 14, while many may skip right to verse 15.

What’s up with that?

Well, verse 14, if you have it, says this:

Matthew 23:14 LSB
14 [“Woe to you, scribes and Pharisees, hypocrites, because you devour widows’ houses, and for a pretense you make long prayers; therefore you will receive greater condemnation.]

‌If you DO have it, you may have it in brackets, or with an asterisk or some other kind of footnote. 

If you include verse 14, then you would actually have an eighth “woe.” And it certainly does not contradict any teachings of Jesus that we find elsewhere. In fact, the gospels record him saying almost these very things elsewhere. However, in the most reliable manuscripts we have of Matthew, this one verse is not included. So, most translations choose not to include it here, or do so with a footnote or some other way of noting the caveat.

Whether or not you include it in this list, Jesus certainly did condemn the mistreatment of Widows and pretentious prayer.

2. Breeders of Hypocrisy (15)

‌Next, we have verse 15, in which Jesus essentially accuses them of being breeders of hypocrisy.

‌They are continuously reproducing amongst themselves…raising up new scholars and “teachers” among them, passing on their own hypocritical ways, and thus enabling a perpetual cycle of corruption and other problems. 

Rather than living honestly and humbly before each other…rather than learning from each other and growing together, rather than confessing, and repenting together, they instead developed  a system over time which fed into their ego, their pride, their comfort, and prestige, with each generation becoming even worse than the last.

The result is a group of very intelligent, but very foolish individuals, completely caught up and engrossed by self-righteousness, and ignorant of the truth standing right in front of them.

3. Blind Guides (16-22)

‌In fact, the very next thing he calls them is “Blind” in verse 16. “Blind Guides,” he calls them.

How many of you would get on a bus, or in a taxi, if you knew the driver was blind?!? Nobody! It’s a death wish! That’s what Jesus is saying is happening, by people jumping on board with the pharisees, they are unwittingly jumping aboard a vehicle hurdling towards disaster.

To illustrate their blindness, Jesus draws attention to their teaching on making oaths. Apparently, they placed more emphasis on the physical elements, the gifts that were placed on the altar, the gold in the temple, than on the sacred presence of God which they represented. Blindness!

By drawing distinctions between the physical elements of the temple when making an oath, they’ve demonstrated a complete obscurity to the reality of God himself being invoked as a witness to an oath. That’s what makes an oath binding! In fact, a simple commitment to truth and integrity ought to be all that’s needed to make an oath binding! Let your yes be yes, and your no be no! There’s no need to swear on any object, Let alone trivial distinctions between swearing on one object or another. Blindness!

‌4. Misguided Enthusiasm (23-24)

‌This blindness leads into the misguided enthusiasm we see described in verses 23-24. I think this example is actually pretty funny…he turns as he so often does to the use of hyperbolic imagery to make his point. He describes them as being so meticulous when it comes to details that they would filter out a tiny gnat from their cup, but so blind to the bigger issues that they would swallow a whole camel that was swimming in the same drink.

It’s an absurd image, which illustrates the absurdity of their zealous attention to making sure tithes were paid for every last spice in the spice cupboard, while forgetting all about what really matters: justice, mercy, and faithfulness!

Realize that he’s not saying it’s wrong to filter out the gnat…it’s just ridiculous to filter out the gnat but ignore the camel! 

If we focus primarily on the things that DO matter the most, the smaller things will either fall in place, or we’ll realize they’re not worth spending too much time or energy worrying about.

5. Filthy Sparkling Dishes (25-26)

The next two images are very similar…first he describes them as dishes which have been cleaned and scrubbed meticulously on the outside…and yet remain filthy dirty on the inside.

‌If you had to choose to drink out of a cup that had been washed on the inside or the outside, which would you choose?

Of course when we wash dishes, we try to get the whole thing clean, but if we had to choose, the priority would always have to be the inside, right?

And yet, the pharisees put ALL their priority on the outside, while completely neglecting, forgetting about the inside.

6. Whitewashed Tombs (27-28)

‌Verses 27 and 28 provide a similar image, of “whitewashed tombs.” They are like the outside of a grave, that has been beautifully decorated and painted, but which in reality is just a covering for death and rotting flesh.

Faithlife Study Bible Chapter 23
Jews would paint their tombs white so that other Jews would not become unclean through inadvertent contact with a corpse (compare Num 19:16; Luke 11:44). Whitewashed tombs were especially common during the Jewish festivals, when many travelers visited Jerusalem.

CSB Study Bible: Notes Chapter 23
First-century Jews whitewashed the tombs in Jerusalem to alert people to their location so they would not unintentionally draw too near and thus defile themselves. The whitewash also beautified the tombs. Despite this outer beauty, Jewish purity laws regarded the inside of tombs as defiled. Jesus said this resembled individuals whose outer piety (the whitewash) masks an inner corruption (spiritual defilement).

Jesus is not condemning the practice of whitewashing or even decorating tombs in first century Jerusalem, he’s condemning the resemblance of those tombs to the lives of the Pharisees.

7. Proud of a Shameful Legacy (29-36)

‌That said, he does continue on that train of thought, bringing up the tombs of their ancestors, and the prophets of old. In verses 29-36, Jesus essentially accuses them of acting either 

-Proud of a shameful legacy or

-Proud that they are so much better than their ancestors

‌When in reality they are just as bad or worse than their ancestors who murdered the prophets that came before Jesus. And he says they will be held accountable for their sin just as much as their ancestors.


‌These seven “woes” or “judgments” are dire warnings to the religious leaders of Jesus’ day, and should be read primarily within that immediate context. These warnings are specifically for the people Jesus was addressing in that moment. 

But they also serve to warn us against religious hypocrisy today. We are called to true godliness, sincere love, and enduring faith. 

Pretension, affectation, and hypocrisy will only lead to woe. Sorrow.

Lament (vs 37-39)

And it’s with Sorrow that Jesus concludes this section, in verses 37-39.

‌Matthew 23:37–39 LSB
37 “Jerusalem, Jerusalem, who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, the way a hen gathers her chicks under her wings, and you did not want it. 38 “Behold, your house is being left to you desolate! 39 “For I say to you, from now on you will not see Me until you say, ‘BLESSED IS HE WHO COMES IN THE NAME OF THE LORD!’”

Jesus, after having said all this against the Pharisees, is upset…but he’s not angry. He’s moved with grief. Grief for his children, for the city of Jerusalem and everything it could have been but rejected.

Despite the severe judgment he had just pronounced against Israel, he truly longed for them to repent and receive God’s grace!


‌There’s quite a bit in this chapter.

‌Ultimately, the core message is a warning against hypocrisy. Hypocrisy is fueled by pride, greed, and callousness, and it’s a trap that any one of us can easily fall into. 

‌Do your friends, your family, your coworkers know that you follow Jesus? That you “go to church” or, more accurately, are a part of a church? They should! We are not ashamed of the gospel.

‌But those around us shouldn’t just “know” that we are Christians because we say so, or because we wear shirts with churchy puns, or post verses on Facebook. They should also “see” that we are Christians…it should be evident by our lives, in our love for each other and Christ-like humility and service.

‌We must also strive to live in a manner worthy of our calling. If our lives…our attitudes, our language, our actions…if the outward expression of what’s inside doesn’t reflect the transformative power of the Spirit in our hearts, then we’re just pretenders! 

‌Of course, none of us is perfect, and we must be humble and willing to confess and repent to each other, as well as be graceful and forgiving to each other.

‌Even those teachers and leaders who we most respect also have flaws, and we have to recognize that nobody is perfect. Like Jesus pointed out, even with the pharisees, they did say the right things…he said “listen to what they say, just don’t imitate what they do. 

‌One fairly recent and public example that comes to mind is the capstone to the legacy of Ravi Zacharias. Anybody familiar?

‌He was a prominent Christian scholar, apologist, and public speaker. He delivered some incredible speeches and engaged very thoughtfully and logically in many of the most difficult topics and questions that come from those questioning Christianity. Unfortunately, soon after his death in 2020, a disturbing sexual scandal was uncovered, and many people I think were somewhat disillusioned by it.

‌Now, what he did was terrible, but that doesn’t mean that everything he ever said was wrong. But it shows that our salvation is ultimately dependent on God, not the people who he may use to draw us to him.

‌Just because nobody is perfect doesn’t mean God doesn’t still use each of us in his redemptive work. I’m very thankful for the many pastors, teachers, professors, friends and family, theologians and writers, from whom I’ve learned and continue to learn. They are great gifts to the church!

‌Although God has gifted the church with teachers and leaders, nobody is of higher importance in the kingdom than another. Our identity and value does not come from our mentors and guides, but from the one true teacher and guide that we all have in common. Because we would ALL be blind without Him.

‌We should be cautious before offering our lives as an example of Christian living, and yet we ought to strive towards that ideal. And we can learn so much from each other, provide accountability for each other, and sharpen each other. Discipleship…both in leading and receiving, is how we grow and mature in our faith together…but it’s for the sake of unity and growth, not to elevate ourselves or anyone else over another.


Woe, Woe, Whoa!