Matthew Chapter 23 – Commentary and Explanation Bible Study
Matthew 23 is one of those chapters in the gospel where Jesus doesn’t hold back. He speaks with authority, with boldness, with that sharp edge of truth that cuts through pretension. If you’ve ever read it, you probably remember that tone – it’s fiery, it’s passionate, it’s almost like a thunderstorm rolling over a city. And it is directed mostly at the scribes and the Pharisees, the religious leaders of His day, who had turned what should be a living, breathing faith into a performance, a burden, and often a stage to show off.
When I read this chapter, honestly, it stings a little. Because it’s not just about Pharisees two thousand years ago. It’s about me, it’s about us, about the human tendency to drift into appearances rather than heart, into rules rather than love, into being seen rather than actually living rightly. Jesus’ words are harsh, yes, but also strangely freeing if we let them settle.
Let’s go step by step, story by story, almost like we’re sitting with a warm cup of tea or maybe coffee, maybe you like yours sweet or bitter, whichever, and we let Jesus’ words sit with us, challenge us, and maybe even make us squirm a little.
Verses 1–4: Jesus Speaks to the Crowd and His Disciples
“Then Jesus said to the crowds and to his disciples: ‘The scribes and the Pharisees sit in Moses’ seat. So you must be careful to do everything they tell you. But do not do what they do, for they do not practice what they preach. They tie up heavy, cumbersome loads and put them on other people’s shoulders, but they themselves are not willing to lift a finger to move them.’”
Right from the start, Jesus sets the scene. He’s speaking to two groups: the crowds (ordinary folks like fishermen, mothers, kids running around with dusty feet, farmers with calloused hands) and His disciples (those following Him more closely, learning, sometimes confused, sometimes bold).
He acknowledges the scribes and Pharisees have authority. “Moses’ seat” was like saying they are the teachers, interpreters of the law. They’re not nobodies. They’re the experts. And Jesus doesn’t say “ignore them” – He says listen to what they teach, but don’t copy how they live.
That line “they do not practice what they preach” – we throw it around in our culture a lot, don’t we? It’s become almost cliché, but here it’s deadly serious. It’s one thing to have knowledge, another to live it. And then, the image He gives… they pile up heavy burdens. Think about it: imagine someone stacking sacks of grain on your back, one after another, until you can barely stand. That’s what these leaders did with rules and rituals, endless details that suffocated instead of giving life.
And worst of all, they wouldn’t help. No compassion. No reaching down to lift the load. Just commands shouted from above.
I remember once when I was a teenager, a leader in church gave us such strict rules about how to pray, almost like a checklist – “do this first, then that, don’t forget these words” – that I felt scared to even speak to God in my own way. It felt heavy. But then another older lady in the church told me one night: “Honey, prayer is just talking to Jesus like He’s your best friend.” That’s the difference. One ties burdens, the other lifts them.
Verses 5–7: Doing Things to Be Seen
“Everything they do is done for people to see: They make their phylacteries wide and the tassels on their garments long; they love the place of honor at banquets and the most important seats in the synagogues; they love to be greeted with respect in the marketplaces and to be called ‘Rabbi’ by others.”
Jesus exposes their motives. They’re religious, yes, but it’s a performance. Their phylacteries (little leather boxes with Scripture inside, worn during prayer) they made bigger, more noticeable. Tassels on their garments, which were supposed to remind them of God’s commands, they lengthened just so people would say, “Wow, look how holy he looks.”
It’s kind of like today’s version of showing off your spirituality on social media – the perfect Bible verse with the perfect coffee cup, or making sure everyone sees how many good deeds you’ve done. Nothing wrong with posting Scripture, don’t get me wrong, but when the heart behind it is “look at me” instead of “look at Him,” well, we’re walking in Pharisee shoes.
They loved the spotlight – the special seat at dinner, the respectful greetings, the titles. And honestly, don’t we all crave a little recognition sometimes? It feels nice when someone calls you wise or holy. But Jesus sees through it.
Verses 8–12: True Greatness
Here Jesus flips everything upside down.
“But you are not to be called ‘Rabbi,’ for you have one Teacher, and you are all brothers. And do not call anyone on earth ‘father,’ for you have one Father, and he is in heaven. Nor are you to be called instructors, for you have one Instructor, the Messiah. The greatest among you will be your servant. For those who exalt themselves will be humbled, and those who humble themselves will be exalted.”
It’s radical. He tells His disciples – don’t chase titles, don’t chase recognition. You’re all siblings under one Father. And greatness? It’s not in sitting on top of others but in kneeling down to serve.
I remember washing dishes once after a church potluck. Nobody wanted that job. The food was eaten, laughter was loud in the fellowship hall, but the kitchen was a mess. And I grumbled at first, hot water burning my hands. But in that quiet corner, scrubbing pans, I suddenly felt a weird joy – like Jesus was there beside me, saying “This is greatness. This is serving.” It wasn’t glamorous, but it was real.
That’s the kingdom Jesus teaches.
Verses 13–36: The Seven Woes
This is the heart of the chapter. Jesus pronounces seven “woes” – basically laments or judgments – against the scribes and Pharisees. And each one is like a lightning strike. Let’s walk through them.
Woe 1: Shutting the Door of the Kingdom (v. 13)
“You shut the door of the kingdom of heaven in people’s faces. You yourselves do not enter, nor will you let those enter who are trying to.”
Instead of opening doors, they slammed them shut. Religion became a gatekeeping tool. I wonder how many people today feel shut out of church because of hypocrisy, judgmental attitudes, or endless rules. That’s still Pharisee behavior.
Woe 2: Devouring Widows’ Houses (v. 14 – some manuscripts)
They took advantage of the vulnerable, using religion as cover. That’s exploitation, and God sees it.
Woe 3: Making Converts Twice as Bad (v. 15)
“You travel over land and sea to win a single convert, and when you have succeeded, you make them twice as much a child of hell as you are.”
Harsh words! But Jesus is saying: what’s the point of evangelism if you’re just passing on a toxic, empty religion?
Woe 4: Blind Guides (vv. 16–22)
They made silly rules about oaths – swearing by the temple meant nothing, but swearing by the gold of the temple mattered. Jesus calls them blind. They valued objects more than God’s presence.
Woe 5: Straining Out a Gnat, Swallowing a Camel (vv. 23–24)
This one always makes me smile. They obsessed over tithing tiny herbs like mint and dill, but ignored justice, mercy, and faithfulness. Picture someone straining their soup to make sure no tiny bug is in it, then gulping down a whole camel by mistake. That’s absurd, but it’s how misplaced priorities look.
Woe 6: Clean Outside, Filthy Inside (vv. 25–26)
They cleaned the cup’s outside but inside it was dirty. Jesus is pointing at hypocrisy again – outward appearance of holiness but inner greed and self-indulgence.
Woe 7: Whitewashed Tombs (vv. 27–28)
“You are like whitewashed tombs, which look beautiful on the outside but on the inside are full of the bones of the dead and everything unclean.”
Wow. That’s vivid. Tombs were painted white to look nice, but inside? Rotting death. Same with Pharisees – outward beauty, inner decay.
Woe 8: Killing the Prophets (vv. 29–36)
They honored prophets from the past but were about to kill the greatest prophet – Jesus Himself. Their fathers killed the messengers of God, and they would continue that legacy.
Verses 37–39: Jesus Weeps Over Jerusalem
At the end, His tone shifts. It’s no longer thunder; it’s sorrow.
“Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, and you were not willing.”
What an image – a mother hen spreading her wings, trying to protect her chicks from danger, but they scatter. That’s Jesus’ heart. He wanted to gather, to shelter, to love. But they refused.
And so He says, “Look, your house is left to you desolate.” The temple, the city, would face judgment. Yet He leaves a door open: “You will not see me again until you say, ‘Blessed is he who comes in the name of the Lord.’”
Reflections for Us Today
Reading Matthew 23 is like holding up a mirror. It’s easy to point fingers at Pharisees, but I see pieces of them in me too. Don’t you?
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When I crave recognition instead of quietly serving.
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When I care more about rules than people.
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When I polish my outside while ignoring my inside.
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When I make faith feel like a burden instead of a joy.
And yet, Jesus’ harsh words are also merciful. He’s shaking us awake, pulling us out of dead religion and into living relationship.
I think of that hen imagery again – wings spread wide. That’s still His heart for us. Not to crush us with burdens, not to shame us into performance, but to gather us close, safe, real.
Closing Thoughts
Matthew 23 is heavy, yes, but it’s necessary. It reminds us that God isn’t fooled by appearances. He cares about the heart. He calls out hypocrisy, not to destroy us, but to free us from it.
Sometimes, we need to hear the thunder. Other times, we need to feel the hen’s wing brush against us. This chapter gives us both.
So maybe next time you’re tempted to show off spiritually, or maybe when you’re tempted to judge someone else for not living up to some “religious standard,” remember: greatness is serving. True holiness is love. And Jesus’ arms are wide, still calling us to come under His wings.
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