A Sermon from Jesus
Weak Preaching
Unqualified observation: There is a lot of “fluff” being preached from current-generation pulpits. You are free to disagree, and if that is not the case where you gather with the saints, then I am pleased and happy for you. But as an observer of the church, as a former pastor, as a contender for the kingdom, that is what I see.
There are myriad reasons underlying this reality, ranging from pastors wanting to protect their own standing with a congregation to wanting to build seeker-sensitive Sunday gatherings, but the confirming material for the fluff-sermon reality is abundant. Those of you who are non-fiction authors, or aspiring authors, can latch onto this idea and run with it. It hasn’t grabbed my heart just yet.
What I do find fascinating is that there is nothing fluffy about Jesus’ material. The contrast between Jesus’ teaching and what flows from many contemporary pulpits is astonishing. Indeed, at one point, Jesus’ teaching was so bold, so strong, so non-seeker-sensitive that huge crowds of people stopped following him. Rather than chase after them with impassioned apologies and assurances that he would do better, Jesus turned to his disciples and said, “You want to leave too? Here’s your chance.”1
Eight Woes From Jesus
Jesus reserved his strongest cannon volleys for the religious leaders—the Pharisees, the Saducees, the scribes. We see just such an assault in Matthew 23, and that is where we land this week.
Blocking Entrance to the Kingdom
Woe to you, scribes and Pharisees, you hypocrites! You shut the kingdom of heaven in men’s faces. You yourselves do not enter, nor will you let in those who wish to enter.
– Luke 10:29, ESV
In his sermon on the mount, Jesus said the kingdom belongs to the poor in spirit. Here, the kingdom is inaccessible to the proud and arrogant. Not only do they not enter the kingdom, but they prevent others from entering. It’s bad enough to not enter the kingdom myself, but woe to me if I block the way for others who seek it. Luke’s gospel records Jesus delivering this same strong message to the scribes, telling them, “You have taken away the key of knowledge. You did not enter yourselves, and you hindered those who were entering.”2
What is truly fascinating to me regarding Jesus’ interactions with the religious elites is that he stood in verbal opposition to all three prominent groups of his day. In contrasting himself with the Pharisees, the Saducees, and the scribes, Jesus stood apart from the conservatives, the liberals, and the legalists. All three groups held to scriptural inspiration and prided themselves on knowledge of the scrolls. Yet they distorted the truth of scripture with such self-serving effectiveness that it earned them this woe from the King.
Greater Condemnation
Woe to you, scribes and Pharisees, you hypocrites! You defraud widows of their houses, and for a show make lengthy prayers. Therefore you will receive greater condemnation.
– Matthew 23:14, ESV (footnote 13c)3
This is an exceedingly strong condemnation of the religious leaders of Jesus’ day, and it serves as a clarion call for any today who would misuse their office as a means of abusing their flocks. The apostle James also cautioned those who would be teachers, saying they would be judged more strictly.4 The apostle Paul wrote to his pupil, Timothy, describing leaders who put on a show of godliness while worming their way into the homes of “weak-willed women” driven by their lusts. They are ever learning but never able to come to a knowledge of truth.5 These men are to be avoided.
Sons of Gehenna
Woe to you, scribes and Pharisees, you hypocrites! You traverse land and sea to win a single convert, and when he becomes one, you make him twice as much a son of hell as you are.
– Matthew 23:15, ESV
This is not theatrical rhetoric from a lively Broadway play. This is God incarnate in the person of Jesus speaking his heart and mind, and he just called the protégés of these religious leaders “double sons of hell.” Elsewhere Jesus told these same people that they were sons of the devil.6 They resisted the truth with such ferocity that they were ready to kill, if doing so would silence their opposition.
Do not be fooled. Using the clearest of language, Jesus said those who hate truth and hate God will hate you as well. The world hates you. The same world that persecuted Jesus will persecute you.7 We are fast approaching the 250th anniversary of the United States, a country where we have enjoyed freedoms centered on godliness and righteousness, but forces of secularism and atheism have eroded those foundations and found boldness to spew messages of unprecedented filth and hatred. May we exude even greater boldness advocating for truth.8
Sons of Gehenna
Woe to you, blind guides! You say, “If anyone swears by the temple, it means nothing; but if anyone swears by the gold of the temple, he is bound by his oath.”
– Matthew 23:16-22, ESV
It is dangerous to follow a guide who does not know where they are going, but sheer folly to follow a blind guide. Jesus says that when the blind lead the blind, both will fall into a ditch.9
I remember, as a child, having to “swear” to this or that. Maybe I had to swear I would give back a toy I borrowed, or that I wouldn’t reveal a secret.
You swear you won’t tell?
Yeah, I swear.
You double swear you won’t tell?
Yeah, yeah, I triple swear!
You swear on the Bible?
Yeah, on a whole stack of Bibles, a mile high!
When I am in some sort of negotiation and the other party asks me to promise or swear I’ll do something, I refuse to do so. This may seem silly to you, but I take Jesus seriously when he says, “Let your ‘yes’ be a ‘yes’ and your ‘no’ be a ‘no,’ because anything beyond that comes from evil.”10 As a Christ-follower, your integrity is intact and your word is sufficient. No grandiose oaths are needed. Anything else is blindness.
Weightier Matters
Woe to you, scribes and Pharisees, you hypocrites! You pay tithes of mint, dill, and cumin. But you have disregarded the weightier matters of the law: justice, mercy, and faithfulness. You should have practiced the latter, without neglecting the former. You blind guides! You strain out a gnat but swallow a camel.
– Matthew 23:23-24, ESV
I’m going to confess that I struggle with this one, because obedience matters. Jesus is King, and I am a subject of the King. The King issues edicts and rightfully expects his subjects to obey—to comply. That said, the same King is declaring here that the letter of the law does not override the spirit of the law. I find a minor comfort in the fact that Jesus confirms we should practice the spirit of the law while not neglecting the letter of the law. Let me give you an example.
I once saw a woman being baptized into Christ, nose pinched, eyes closed, and laid back into that watery grave. It was a beautiful thing, and I was thrilled for her. But what seemed silly to me was that she was immediately baptized again because one of the onlookers observed that her left hand didn’t go completely under the water, so technically she was not “fully immersed.”
Okay. Technically, that’s true. But in the spirit of the law, the woman submitted to being baptized as obedience to an edict from the King. What’s the weightier matter of the law here? The technicality that her left hand was above the water, or that her heart was obediently bowed before the King of majesty? Be as obedient to the King as you can be, but walk knowing he is also the King of grace and mercy.
Undoubtedly part of Jesus’ objection to these men is that they made a public show of their obedience,11 while harboring hearts of stone. The yielded heart is the heart that quietly feeds the hungry, waters the thirsty, shelters the stranger, clothes the naked, visits the sick andthe imprisoned.12
Polished Exteriors
Woe to you, scribes and Pharisees, you hypocrites! You clean the outside of the cup and dish, but inside they are full of greed and self-indulgence. Blind Pharisee! First clean the inside of the cup and dish, so that the outside may become clean as well.
– Matthew 23:25-26, ESV
As a new Christ-follower in the 1980s, I learned quickly that the tangible sins were easy to overcome. It was the intangible ones that took time, effort, and willingness to surrender to the mind of Christ. It’s easy to change what you do. Discipline and self-control can master those things. Even the world knows that. What’s both more difficult and more impactful is surrendering and allowing Jesus to change who we are, the intangibles, the heart, the conscience, the will.
Jesus taught that “Out of the abundance of the heart the mouth speaks.”13 Paul taught that circumcision of the Spirit is circumcision of the heart,14 and that the Law once inscribed on tablets of stone is now written on our hearts.15 One of the most challenging lessons for any Christian to learn and master is that Christianity is not a matter of hands and feet, but hearts. It is not about what I do, but about who I am. And to drive this important truth home, Jesus will say it again, differently.
Woe to you, scribes and Pharisees, you hypocrites! You are like whitewashed tombs, which look beautiful on the outside but on the inside are full of dead men’s bones and every kind of impurity. In the same way, on the outside you appear to be righteous, but on the inside you are full of hypocrisy and wickedness.
– Matthew 23:27-28, ESV
One of the most off-putting human characteristics for me is pretense. Pretense, of course, is just a more pleasant word for hypocrisy—pretending to be something or someone I am not. The core of pretense is the intent to deceive, to use my actions, words, and appearance to persuade you of what is not true about me. For us in the body of Christ, this is the attempt to look like and talk like disciples of Jesus while inwardly being full of dead men’s bones. It is the ravenous wolf who wants to look like a shepherd of the sheep.16 God cautioned the prophet Samuel, saying, “Don’t be impressed by outward appearance. Man looks at outward appearances, but Yahweh looks at the heart.”17
Self-Condemnation
Woe to you, scribes and Pharisees, you hypocrites! You build tombs for the prophets and decorate the monuments of the righteous. And you say, ‘If we had lived in the days of our fathers, we would not have been partners with them in shedding the blood of the prophets.’ So you testify against yourselves that you are the sons of those who murdered the prophets. Fill up, then, the measure of the sin of your fathers. You snakes! You brood of vipers! How will you escape the sentence of hell?
– Matthew 23:29-32, ESV
I’ve heard it said, “Oh, if I were there in the garden at the beginning, I would not have bitten the fruit.” Oh, of course you would have. So would I. In the passage above, the same hypocrites who claim, “Oh, we would never have murdered the prophets of God,” were actively planning to murder the one standing in front of them.
Building on the previous woe, this woe declares the ultimate outcome of duplicitous behavior—complete separation from God, separation from all that is true and holy and loving and good. That should send a chill up all our spines. Jesus said that what comes out of our mouths proceeds from our hearts and that condemns and defiles us.18 You want to know what is in your heart? Listen to your mouth. What dominates your speech? That’s the truest barometer of where your heart is.
For out of the abundance of the heart the mouth speaks.
I tell you, on the day of judgment people will give account for every careless word they speak, for by your words you will be justified, and by your words you will be condemned.
– Matthew 12:34b, 36-37, ESV
Guard your heart with all diligence, brothers and sisters, for it is the wellspring of life.19
1. John 6;66-67
2. Luke 11:52
3. The earliest manuscripts (such as Codex Sinaiticus and Codex Vaticanus) do not contain Matthew 23:14. The identical concept, however is found in both Mark 12:40 and Luke 20:47.
4. James 3:1
5. 2 Timothy 3:5-7
6. John 8:44
7. John 15:18-2
8. Acts 4:29
9. Matthew 15:14
10. Matthew 5:33-37, James 5:12
11. Matthew 6:1-4
12. Matthew 25:35-36
13. Matthew 12:34
14. Romans 2:29
15. 2 Corinthians 3:3
16. Matthew 7:15
17. 1 Samuel 16:7
18. Matthew 15:18
19. Proverbs 4:23






