Woe is Me! False Shepherds Guarding the Door

Matthew 23 is not gentle. Jesus is not smoothing over confusion. Jesus is confronting rebellion, naming the scribes and Pharisees, naming their sin, and pronouncing woe. The word woe carries horror, anguish, coming judgment, and sorrow. Amos 5 helps give the word its weight, because God spoke woe over people who thought the day of the Lord would mean safety for them, when their sin meant darkness instead of light.

Matthew 23 does not let the warning stay at a safe distance. The warning turns from “woe to you” toward sober self-examination. False shepherds do not merely refuse Christ. False shepherds block the way for others. The passage warns the church to ask both questions, who is shepherding a soul, and where is that soul shepherding others?

Jeremiah and Ezekiel show that God has always taken false shepherding personally. Jeremiah says, “Woe to the shepherds who destroy and scatter the sheep of my pasture.” Ezekiel says the shepherds fed themselves instead of feeding the sheep. God says, “I am against the shepherds,” because the sheep belong to him. The scribes and Pharisees stand in that same terrible line. They have the Scriptures, but they do not use them to point to Christ. They have influence, but their influence is destructive.

Jesus says they shut the kingdom of heaven in people’s faces. The image is devastating. The kingdom has a door, and these men stand in front of it. They do not enter themselves, and they do not allow those entering to go in. Religious position does not open the kingdom. Christ does.

Paul gives the right picture of influence when he says, “Be imitators of me as I am of Christ.” Paul is not gathering disciples around himself. Paul is a signpost. The Pharisees are a roadblock. True discipleship labors until Christ is formed in people, not until people become copies of another person’s preferences.

Verse 15 makes the warning even sharper. False shepherds are not always lazy. Sometimes they are zealous. They cross land and sea to make a convert, but zeal detached from Christ does not produce life. It reproduces death. Romans 10 says Israel had zeal for God, but not according to knowledge, because they sought to establish their own righteousness instead of submitting to God’s righteousness.

The gospel is not moral improvement, religious performance, or self-made righteousness. The gospel is Christ crucified and risen for sinners. “Nothing in my hand I bring, simply to the cross I cling.” Christ is the door. The false shepherds shut the door, but Christ opened the way by his own blood.

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Key Takeaways

• 1. Woe carries grief and judgment The word “woe” is not petty frustration or religious name-calling. Jesus speaks judgment with sorrow, because spiritual danger is real and mercy still calls before judgment falls. A warning that severe is not coldness from God, but grace refusing to flatter people on the road to destruction. [27:02]
• 2. Influence can become a roadblock The scribes and Pharisees were not only outside the kingdom. Their influence stood in front of the door and made Christ harder to see. Every form of spiritual influence either clarifies Christ or puts something else in the way, even when that something is religious language, tradition, personality, or personal preference. [35:37]
• 3. Zeal without Christ reproduces death The Pharisees crossed land and sea to make converts, but Jesus did not call their zeal faithfulness. Zeal detached from Christ can make people more confident in error, more defensive in self-righteousness, and more hardened against mercy. Energy for religion is dangerous when it trains sinners to build a resume instead of come empty handed to God. [47:56]
• 4. The gospel has one door Jesus does not close the door by saying, “I am the way.” Jesus stands at the door and calls sinners to mercy through the only Savior God has given. Any gospel that removes repentance, mixes grace with merit, or makes Christ less than sufficient leaves sinners outside with religious confidence instead of salvation. [55:48]
• 5. Christ gathers what false shepherds scatter Jeremiah’s woe against false shepherds also carries a promise of a righteous Branch from David. False shepherds burden, scatter, and feed themselves, but Christ carries the burden, gathers his sheep, and gives himself. The only safe response is to enter through Christ and spend a life pointing others to him. [62:13]

Youtube Chapters

• [00:00] - Welcome
• [24:25] - Reading Matthew 23
• [25:49] - Why Verse 14 Is Skipped
• [26:13] - Jesus Confronts Rebellion Directly
• [27:02] - The Weight Of Woe
• [30:01] - Guarding Against False Shepherding
• [31:43] - False Shepherds In The Old Testament
• [35:11] - Standing In Front Of The Door
• [37:29] - Imitating Christ, Not Personal Image
• [43:31] - The Key Of Knowledge
• [46:23] - Zeal That Leads Away From Christ
• [54:48] - Softening The Gospel
• [57:27] - The One True Gospel
• [61:43] - The Door Is Still Open
• [63:53] - Closing Prayer

Bible Reading

Matthew 23:13,15
“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. 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.” [25:00]

Jeremiah 23:1-2
“Woe to the shepherds who destroy and scatter the sheep of my pasture! declares the Lord. Therefore thus says the Lord, the God of Israel, concerning the shepherds who care for my people: ‘You have scattered my flock and have driven them away, and you have not attended to them. Behold, I will attend to you for your evil deeds, declares the Lord.’” [32:15]

Ezekiel 34:2-4
“Son of man, prophesy against the shepherds of Israel; prophesy, and say to them, even to the shepherds, Thus says the Lord God: Ah, shepherds of Israel who have been feeding yourselves! Should not shepherds feed the sheep? You eat the fat, you clothe yourselves with the wool, you slaughter the fat ones, but you do not feed the sheep. The weak you have not strengthened, the sick you have not healed, the injured you have not bound up, the strayed you have not brought back, the lost you have not sought, and with force and harshness you have ruled them.” [33:51]

Romans 10:1-3
“Brothers, my heart's desire and prayer to God for them is that they may be saved. For I bear them witness that they have a zeal for God, but not according to knowledge. For, being ignorant of the righteousness of God, and seeking to establish their own, they did not submit to God's righteousness.” [49:04]

Amos 5:18
“Woe to you who desire the day of the Lord! Why would you have the day of the Lord? It is darkness, and not light.” [27:38]

Observation questions

1. In Matthew 23:13, what two things do the scribes and Pharisees refuse to do in relation to the kingdom of heaven? [41:31]
2. In Jeremiah 23 and Ezekiel 34, what are some specific ways false shepherds fail the sheep?
3. According to Amos 5:18, how is the word “woe” connected to darkness rather than safety? [27:54]
4. In Matthew 23:15 and Romans 10:1-3, what is observed about religious zeal when it is separated from the righteousness God gives in Christ? [49:47]

Interpretation questions

1. Jesus says the scribes and Pharisees “shut the kingdom of heaven in people’s faces.” What does that image suggest about how religious influence can actively keep people from Christ, not just fail to help them? [41:01]
2. God says, “I am against the shepherds,” because the sheep belong to him. What does that reveal about how personally God takes false shepherding and spiritual misuse of people? [34:31]
3. Paul can say, “Be imitators of me,” while Jesus condemns leaders who gather people around themselves. What is the difference between influence that acts like a signpost and influence that becomes a roadblock? [38:52]
4. Romans 10 says people can have zeal for God while still seeking to establish their own righteousness. Why is self-made righteousness so dangerous, especially when it looks sincere and serious? [50:36]

Application questions

1. Every person has some spiritual influence somewhere. In what relationships or settings does that influence show up most clearly right now? Does that influence make Christ clearer, or does it tend to put personality, preference, or pressure in the way? [36:23]
2. A person can live a very religious life and still make Christ harder for others to see. Have there been times when Christianity was presented more as rule-keeping, culture, or appearance than as coming to Christ empty-handed for mercy? How has that affected the way faith is lived out? [42:38]
3. False shepherding is not always loud or obvious; sometimes it softens hard truths. What kinds of teaching or instincts are most tempting to accept right now: removing repentance, adding merit to grace, or making Jesus seem less exclusive than he is? [56:17]
4. Zeal alone is not proof of truth. Where is there a tendency to mistake passion, activity, confidence, or strong religious language for faithfulness to Christ? How can that be tested carefully by Scripture? [56:54]
5. The warning turns inward with the question, “What am I reproducing in the people around me?” In family, friendship, or church life, are others being shaped toward honest repentance, deeper trust in Christ, and love for the gospel, or mainly toward habits and preferences? [54:15]
6. Christ is the one door, and sinners enter through him alone. Is there present trust in Christ himself, or is there still some quiet dependence on church involvement, moral effort, knowledge, or a spiritual resume? [45:05]
7. Christ gathers what false shepherds scatter and gave himself for the sheep. What would it look like this week to spend ordinary moments pointing someone more clearly to Christ rather than to self? [01:03:23]