Jesus Crossed Boundaries: The Religious and the Righteous

Jesus Crossed Boundaries: The Religious and the Righteous

Jesus Crossed Boundaries: The Religious and the Righteous.

“Then Jesus said to the crowds and to His disciples, ‘The scribes and the Pharisees sit on Moses’ throne as the authorized interpreters of the Law. So listen and follow what they teach, but don’t do what they do, for they tell you one thing and do another. They tie on your backs an oppressive burden of religious obligations and insist that you carry it, but will never lift a finger to help ease your load.” (Matthew 23:1-4, TPT).

Woe unto you: What sorrow awaits you; alas for you; distress is headed your way; you’re asking for trouble; grief is coming for you; how unfortunate you are; your destiny will involve nothing but suffering; you’re hopeless.

Hypocrite: Pretender; fraud; phony; imposter; play-actor; fake.

Scribe: ‘Men of Letters,’ since the Greek word for scribe is “gramma,” the source for our word “grammar;” religious scholar; teacher of religious law; lawyer; interpreter of Torah; member of Temple leadership; associated with the Pharisees because most of the scribes belonged to the Pharisee party.

Pharisees: A popular religious party operating in 1st century Israel. They were respected for their scholarly knowledge of Scripture and for their interpretation of the written word and oral law. They were highly influential in the local synagogues. They were laymen, not priests, and came from all classes of people. They believed in the bodily resurrection of the dead and eternal life, which was earned by good works according to Mosaic Law. They emphasized extreme detail regarding observance to the Jewish law, which made them separatists from anything non-Jewish. They were committed to righteousness and obeying all of God’s laws, but often found themselves following the letter of the law at the expense of the spirit of the law, blind to the law’s true intent.

Number Seven: This number signifies wholeness, perfection, completeness. It is St. Matthew’s favorite number, for example there are seven petitions in the Lord’s Prayer, forgiveness not 7 but 77 times, there is a natural division of his gospel into seven sections, and now there are seven woes from Jesus.



  1. Opening Salvo.
  2. The Seven Woes.

III. The Closing Lament.

  1. The Pharisee in Me. 



Jesus wanted dearly to purify the religious establishment of the Temple during His time. He wanted to cross that boundary and bring true righteousness to what constituted keepers of the Law of Moses. In seeking the purification of the religious, He had no choice but to confront it head-on. With the seven woes in Matthew 23, Jesus was living into His OT prophetic style of communication. And He enjoyed the perfect backdrop for the Woes… the Temple. Isaiah was the best-known prophet in the Hebrew Bible who employed a “woe unto you” confrontation. In Isaiah’s case, he was calling the people of Judah to task for their exploiting of others, their drunkenness, their pride and arrogance, their confusing of moral standards, and their perverting of justice. Jesus used this “woeful” prophetic formula to critique not the people of Israel but the Temple leadership for their mean-spirited hypocrisy and their superficial, self-righteous ambition. There are actually eight woes technically in this Matthew passage, but one of them wasn’t in the original manuscripts, and so scholars say it was added to the gospel after first being written. So this eighth woe (“you devour widows’ houses“) is not considered an official woe of Jesus. He proclaimed seven woes, the perfect number, the complete number. This passage, Matthew 23, is Jesus’ most famous attack on the scribes and Pharisees, and has been called “the Grand Critique.” He didn’t mince words, He didn’t hold back in His stinging accusations of the Temple leadership. He basically excoriated them, and straightforwardly told them, I’ve had it with you! I’ve lost my patience with you! You are headed for disaster if you keep leading my people astray!

  1. The Opening Salvo.

If you want to know what makes God angry, read on. Jesus is all fired up after a series of confrontations with the Temple leadership… the scribes, the Pharisees, and the Sadducees. He knows they are plotting to entrap Him, and are trying to figure out ways to stop His ministry dead in its tracks. In Matthrew 23 we find Jesus verbally cleansing the Temple. He did verbally what He had just done physically, clearing the Temple of unworthy riffraff and a host of impurities. Jesus had several pointed criticisms of them here at the start in the first few verses. And He was only getting warmed up! He threw in these zingers even before moving on to His prophetic woes. He accused them of not bothering to practice what they preach, of knowing the Scriptures but not living by them. He accused them of being pretentious, of being impressive at the expense of being spiritual. He accused them of living in a “religious fashion show” (Peterson), of seeking the attention of the people and looking good religiously. Jesus accused them of seeking honor and privilege, of welcoming impressive titles like father, master, and rabbi, titles that are intended to be used for God and not them. He accused them of seeking the admiration of the people instead of directing all the praise to God. Jesus closes this stinging warm-up with accusations of haughtiness, of being vainglorious, of exalting themselves over those who are not as “holy.” Jesus essentially said that, because their eyes are only on themselves, they have lost sight of God. Jesus was worried about the spiritual welfare of the people as well, afraid that the leaders’ spiritual pride and unfruitfulness might spread to the people of Israel. Can anyone dare claim that these accusations are irrelevant to us today? If we are honest with ourselves, we all have at least a little of the pharisee in us.

  1. The Seven Woes.

First Woe: (Matthew 23:13). Woe unto you, scribes and Pharisees, hypocrites and frauds! Your whole religious system doesn’t open the door to God’s kingdom, it shuts the door in people’s faces. Your faulty reasoning of the Law has actually ended up making it impossible to obey. Your legalistic view of the Faith keeps you from entering the kingdom of heaven, and you have kept others from entering as well. The end result of your religious program is that no one is able to enter the kingdom, you or anyone else! Your religious system builds walls, not bridges, and you will be judged for this. 

Second Woe: (Matthew 23:15). Woe unto you, scribes and Pharisees, hypocrites and phonies! Here you are, traveling all over the Roman Empire to persuade even one Gentile to join you in your Faith, but all you’re doing is convincing someone to join a dead religion. When you convert someone to your system, you are drawing them into a religious program in which this convert will focus on the unimportant details like your man-made additional laws and traditions. And your proselyte will miss God, the whole point of Faith! In your propaganda, you will be creating even more hypocrites who don’t make it into the kingdom of God. Your new converts will be fit for the garbage dump outside town, just like you! 

Third Woe: (Matthew 23:16-22). Woe unto you, scribes and Pharisees, hypocrites and pretenders! How can you blindly get all caught up in your own little traditions instead of the Law of the great Moses? Certainly you’re not saying the two are equal! You have added the law about giving an oath that swears by the gold of the Temple. And you have told everyone to swear a promise by the gift at the altar. You blind fools! Make your promises by that which is truly sacred in God’s eyes, not man’s eyes… the Temple, the altar, your own conscience. Obviously, God will hold you to your promise, no matter how it comes about. Don’t do this stupid hairsplitting. It’s laws like this that distract people from God and frustrates their tender faith.

Fourth Woe: (Matthew 23:23-24). Woe unto you, scribes and Pharisees, hypocrites and imposters! Here you go again, playing Temple trivia instead of focusing on the major issues of religion, things like justice, mercy, and faith. You want to make sure everyone pays a tithe on little garden herbs, but then miss the giant matters of the Faith. Go ahead, pay your tithes, big deal, but don’t let them distract you from what’s of more spiritual importance. Once again you are being blind guides for the people, more concerned about minor laws than major religious issues. Do you honestly think you can gain spiritual muscle by lifting these light weights and ignoring the heavy weights? 

Fifth Woe: (Matthew 23:25-26). Woe unto you, scribes and Pharisees, hypocrites and play-actors! You have become so pretentious in your hypocrisy. You are proving yourselves blind once again by being more concerned about ceremonial cleanliness than inner purity. It’s as if you think your job is done when you wash the outside of yourself, ignoring your filthy inside self. You just care about appearances, forgetting that God can peer inside you with perfect vision. And He won’t like what He sees! You want a religion that helps you look good at a superficial level but is unconcerned about things like greed and gluttony at a deeper level. Learn to scrub your insides, purify yourselves, so that it matches the spotless outside, and your religion will really mean something.

Sixth Woe: (Matthew 23:27-28). Woe unto you, scribes and Pharisees, hypocrites and pretenders! You are acting holier than thou so you can hide your sinfulness. You look like saints to the people, but you are corrupted when God scratches beneath the surface. You appear to be law-abiding, but your inner character is committed to lawlessness at the heart of your Faith. You’re like a tomb that is whitewashed so it looks pretty, but walk into that tomb and all you see is a dead man’s bones and the worms eating rotten flesh. You pretend to be pious and full of religious life, but instead you’re self-righteous, dead to God. You holy ones are merely the Great Pretenders. 

Seventh Woe: (Matthew 23:29-35). Woe to you, scribes and Pharisees, hypocrites and frauds! You impudently declare that you would never harm a prophet or a righteous one like your ancestors did, so you proudly decorate the monuments and tombs of those who have had their blood shed in the past. But the truth is that you would have done the same thing as your fathers, and that you will indeed shed the blood of the prophets and righteous believers in your midst. Don’t fool yourselves. You will indeed turn your self-righteous indignation on those sent by God to speak His Word. You claim to have learned from history, but the fact is that, judging by your current behavior, you haven’t learned anything! You’re one big family of poisonous snakes, and you will not escape God’s judgment. 

III. The Closing Lament.

Jesus finally managed to catch His breath after His seven woes to the scribes and Pharisees. He was speaking all this time in the Temple, and so His mind turned to the lost city of Jerusalem, spiritually lost. Jesus admonished the Holy City at this point for its persecution of the earlier prophets. Jesus sorrowfully noted that the messengers of God were badly mistreated in Jerusalem, even stoned and otherwise murdered. What Jesus most feared had happened… the spiritually unfruitful Temple leadership has unfortunately spread to the people. And the result is that the whole city will soon be abandoned by God and emptied of spiritual life. “O Jerusalem, Jerusalem,” Jesus laments. “I see your plight, I see your lost and confused children, and I want to gather you under my wings like a mother hen. But you wouldn’t let me! And soon I will be another Prophet killed by the Temple authorities, another example of how you have treated your prophets in the past. You won’t see me again until I return at the Last Day, and you will all surely declare, ‘Blessed is He who comes in the name of the Lord!’” (Matthew 23:37-39).

  1. The Pharisee in Me. 

First Woe: Do I mentally make a long list of rules not found in Scripture, for everyone who wants to be a part of God’s kingdom? Do I think that these rules must be obeyed if we want to follow Jesus? Do I give other believers the impression that they won’t make it to heaven if they fail to obey this long list? Do some believers simply give up trying after they attempt to follow this list?

Second Woe: When I try to invite new members to my church, do I just use propaganda to bring them into a religious system, or do I engage in a persuasive conversation to help usher them into the kingdom? Which comes first when I spread the Word, my church program or the Gospel? Am I more concerned about my church’s membership or the kingdom’s? Am I aware of potential problems with my own theology when I share the Good News?

Third Woe: Do I tend to give undue importance to church expectations? Have I become nitpicky with principles that aren’t even in Scripture? Have I begun to equate some of our church policies with what is found in the Bible? Do I invest too much emotional energy into church politics, or too much spiritual focus on that which is not of spiritual importance?

Fourth Woe: Am I forgetting what is really important in my Christian faith? Have I started missing the forest for the trees, being more concerned with minor matters than things like showing mercy, doing justice, and walking humbly with God? Am I using good judgment with regard to putting first things first? Am I able to discern what God thinks is most important and top priority in following Jesus?

Fifth Woe: Do I care too much about appearing squeaky clean to others, and not giving enough attention to my inner character? Is my clean image, my spotless reputation, more important than the status of my heart? Why do I focus so much on appearances, on being impressive, and not on how God sees me? Am I more concerned with outer purity than inner purity? Do I deep down believe that I am earning my salvation with good behavior?

Sixth Woe: Am I a holy-roller, someone who wants everybody to think of me as some kind of saint? Do I make myself sound holier when I pray in public? Is it important for me to appear pious at church, at public gatherings? Do I go to prayer meetings to pray, or to be seen as a holy prayer warrior? Does my private devotional life match up with my public persona?

Seventh Woe: Do I delude myself into thinking that I won’t make the same mistakes as earlier believers? Am I somehow made of purer stuff than Christians in the past? Do I actually think I am above it all? Do I subtly take pride in my own righteousness? Do I dare pretend to be invulnerable to the temptations common to everyone else? Do I honestly think I am better than everyone else, all the while knowing that I can make the same mistakes in weak moments?