The King’s Formal Rejection of Israel (Matthew 23:1–39)

Matthew has recounted Jesus’s final entrance into Jerusalem (20:29–21:17), the unrelenting opposition he faced upon arrival (21:18–22:14), and, now, his rebuke of the faithlessness of the nation’s leadership (23:1–39). To state it another way, the King was formally presented to Israel, formally rejected by Israel, and is now formally rejecting Israel in response. And of all the legitimate reasons the Lord had to condemn that generation of his people, it is their hypocrisy that he highlights. It is their hollow religiosity and resolute sanctimony that Jesus can no longer abide. Why? Because hypocrisy is a poison, as deadly as it is sneaky and as pernicious as it is persistent. But if God’s people can learn to identify its characteristics, its symptoms, and its seriousness, catching exposure early, they can treat it effectively with the antidote of humility.


Over the last few chapters, Matthew has recounted Jesus’s final entrance into Jerusalem and the opposition he faced there. Chapter 23, our text today, records Jesus responding in kind. In other words, the King was formally presented to Israel, formally rejected by Israel, and now is formally rejecting Israel.

And of all the reasons Jesus has to rebuke, abandon, and judge this hardhearted people, it’s their hypocrisy he highlights—their pretend faithfulness, make-believe loyalty, and pseudo-worship. And so, in Matthew 23, Jesus calls out Israel’s leadership, warning the crowds of their treacherous hypocrisy, and pronounces seven woes upon them, verdicts rendered by the Supreme Judge himself.

Hypocrisy is a poison, as deadly as it is sneaky. And by eavesdropping on the King’s formal rejection of Israel, people who had ingested this fatal toxin, you and I going to be reminded of its symptoms and seriousness. But we’re also going to find its antidote: that’s humility.

The Poison of Hypocrisy

Let’s begin with the poison of hypocrisy. It’s all over this chapter (vv. 1–3, 13a, 15a, 23a, 25a, 27–29a). The poison had been ingested. Israel’s leaders were supposed to lead God’s people in righteousness, in covenant faithfulness but had failed because they were hypocrites. They claimed a godliness that they didn’t possess.

Jesus, speaking to the crowds and to his disciples, describes what it looks like. Hypocrisy is characterized by oppression (v. 4). This poison makes others pay, blocks God’s grace to others, and makes others carry the burden of guilt. It’s oppressive.

It’s also characterized by theatrics (v. 5). Phylacteries are boxes containing Scripture tied to the forehead or forearm in supposed fulfilment of passages like Deuteronomy 11:18. Tassels, on the other hand, were worn on garment edges as reminders of the call to holiness (see Numbers 15:37-40).

God had given his people ways to remember the importance of a pure and godly heart but Israel’s leaders used to nemonic devices as publicity tools. The phylacteries got bigger and the tassels got longer, supposedly showcasing their great piety. Hypocrisy is theatrical.

Finally, it’s also characterized by self-promotion (vv. 6–7). Wherever they went, these leaders wanted VIP seating, recognition, and fanfare. They loved their title, Rabbi, not only because it’s a title of respect meaning “my teacher,” but because it distinguished them as superior.

This is what the poison of hypocrisy looks like. It’s oppressive, theatrical, and self-promoting. It’s all about image not substance, about the sizzle and not the steak. It’s selfish, self-serving, and self-glorifying.

This is why, still now, one of the worst things you can call someone is a hypocrite. It’s what many were saying when, amidst COVID lockdowns, some politicians were spotted at house parties and restaurants. Are these restriction actually for our safety or are they more acts of oppression, diplomatic theatrics, and self-promotion? It looked, to many, like hypocrisy. That’s the poison Israel’s leaders had consumed, and it’s the poison you and I need to avoid as well.

Now, let’s see where it leads. First, hypocrisy leads to confusion (vv. 13–15). Israel’s leaders are saying, “this way to the kingdom” and “this way to please God” but the only way they know is the way to hell. So people follow them as knowledgable leaders and guides, but end up finding only dead-ends, disillusionment, and pain. “This isn’t the kingdom! How do we get there? Does it even exist? How do we please God? Does he even exist?” Hypocrisy leads to confusion.

Similarly, read verses 16 through 26. How can people be clear on relating to God through things like swearing oaths, temple procedures and significance, tithing, and the pursuit of holiness when their leaders are too concerned with their own image and prosperity to model and teach them. They can’t. Hypocrisy leads to confusion.

And, tragically, confusion often leads to apostasy, or, a falling away from the faith (vv. 15b, 33). Imagine a new convert, not knowing anything other than Jesus saved them, finds themselves in a church that teaches God’s grace but is legalistic in dress code, tithing, behaviours modification, and church involvement. They hear of the exclusivity of the gospel but see the cultural dogma of inclusivity of worship. Where are these hypocritical, mixed messages going to lead? Best case scenario, immaturity, discouragement, and apathy. Worse case, apostasy. This is where hypocrisy leads.

Finally, it also leads to self-deception (vv. 29–30). It’s not only that hypocrites confuse others, they do it to themselves as well. In the case of these leaders, they proclaimed piously that, if they had been there, they would have listened to Jeremiah, Hosea, and Elijah. They would have repented. Eventually, hypocrites start buying what they’re selling, believing their own lies, and give in to self-deception. This is where hypocrisy leads: to confusion, apostasy, and self-deception.

Hypocrisy is poison and Jesus is reminding us of what it looks like and where it leads. But, lastly, he warns about what it brings. In other words, what’s its endpoint? And, as you can guess, it’s not good.

First, it brings guilt (vv. 32–36). The trajectory of hypocritical rebellion has been set and is irreversible. “Because you are like this, here’s what’s going to happen,” Jesus says. “I’m going to send more messengers”—the apostles, for example—“but you’re going to kill and torture them.” While the leaders had just been claiming they are better than their forefathers who opposed God’s prophets, Jesus tells them that’s not the case. They’re going to do the same thing and, because of that, the guilt is going to descend like an avalanche upon this generation. Hypocrisy brings guilt.

It also brings judgement. As I mentioned earlier, the pronouncement of woe is just that, a pronouncement, not a prediction, of judgement (vv. 13, 15, 16, 23, 25, 27, 29). Add to all that, verse 38. I think this is likely referring to more than just temple although certainly that as well. This is the final statement of the King’s rejection of Israel. I think your house refers to the temple, the city, and all those dwelling there. It was all about to be left desolate, barren, empty. Why? Because of hypocrisy.

Finally, hypocrisy brings self-condemnation (vv. 31, 37). All this that is happening, all the confusion, apostasy, guilt, and judgment, it’s all their fault. God wanted to provide for them, protect them, love them. But they were unwilling.

Hypocrisy is an oppressive, theatrical, and self-promoting poison that leads to confusion, apostasy, and self-deception and that brings with it guilt, judgement, and self-condemnation. It’s not to be trifled with, as first century Israel learned, and God wants us to learn as well.

I don’t care what non-Christians say about the church. They don’t know what they’re talking about. But those who belong to the household of God, should, with an open Bible, be willing to criticize the church—not to destroy but to reform and protect.

And, as Christians, I think we can agree that churches are not immune from the poison of hypocrisy. Church scandals, pastoral moral failings, false teaching, and political posturing all evidence our susceptibility. We’ve seen what hypocrisy looks like, where it leads, and what it brings. And when we do, Oakridge should take those as cautionary tales, motivation to make sure our house is in order. There’s too much at stake! Are we striving to practice what we preach, or are we saying one thing and doing another? And to bring it closer to home, are we, as individual members of this church, rooting out hypocrisy in our lives?

The Antidote of Humility

Hypocrisy is a serious issue, a poison we don’t want to ignore and one which many can ingest without knowing it. So, when we realize it’s there, what’s the solution? Let’s look now to the antidote of humility.

Like with hypocrisy, Jesus gives us a glimpse as to what humility looks like, that it’s characterized, at the very least, by obedience to God’s word (vv. 2–3). The leaders were hypocrites. But, Jesus points out that what they were saying, that which was consistent with Moses’s writings, was still right.

Humility in action looks like obedience to God’s word, not necessarily God’s servants. As we know, his servants can fall. His word will stand forever. Follow that which is sure. The antidote to hypocrisy in our lives and in the church is a humility that manifests itself in obedience to God’s self-revelation not to fallen humanity.

And where does this humility lead? When God’s people are humbled to obedience to God’s word they find equality in God’s family (vv. 8–10).

Jesus is speaking to the crowds but I suspect he’s making eye-contact with his disciples. When he leaves, they are going to be the teachers, father-figures, and leaders that Israel’s current leadership failed to be. But they were not to love those roles and titles. That’s drinking the poison of hypocrisy. Instead, taking the antidote of humility, they were to understand they shared one Teacher, Father-figure, and Leader.

Jesus isn’t erasing all distinctions (see Eph 4:11; Heb 13:7, 17). But he is condemning the desire of prominence and recognition within the body. Leadership positions should never be a goal in-and-of themselves, but always viewed as opportunities to serve equals. We’re siblings in Christ, the same before God. Humility leads to equality in God’s family.

Finally, Jesus describes what humility brings. The first thing is exaltation in God’s economy (vv. 11–12). Jesus has taught this same lesson to his disciples before (see 20:20–28). This reversal of fortunes will take place when the earthly kingdom begins. Jesus himself is the greatest example (see Phil 2:5-11). Humility brings exaltation in God’s economy.

It also brings hope in God’s kingdom (v. 39). There’s judgement in this verse. The generation of Israel that rejected their King is now being rejected by their King. The offer has been rescinded.

But not forever! There’s hope! Notice, “until you say.” While the crowds along the street chanted the same words now long ago, the nation as a whole kept silent. However, there is coming a generation when Israel will see their Messiah again and, that time, together will declare in humble acceptance without a hint of hypocrisy, Blessed is he who comes in the name of the Lord! Humility brings hope in God’s kingdom. That it’s coming, certainly.

You see, hypocrisy only grows in the absence of humility. The poison only does its damage when we forget to or refuse to take the antidote God himself has prescribed.

When God’s people do what this generation of Israel failed to do, that is humble ourselves before God, obeying his word and not people, we will experience equality and unity, eventual exhalation and present hope. 


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Josiah has served the Oakridge Bible Chapel family as one of its elders and one of its pastoral staff members since September 2018, before which he ministered as an associate pastor to a local congregation in the Canadian prairies. Josiah's desire is to be used by God to help equip the church for ministry, both while gathered (edification) and while scattered (evangelization). He is married to Patricia, and together they have five children—Jonah, Henry, Nathaniel, Josephine, and Benjamin.

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