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Closing Loopholes: Sermon Text

Text: Matthew 5:27-37
Week 7 in our Rule of Life series
Listen to it HERE. 

Opening illustration

Calvin & Hobbes Loopholes

Loopholes: The ability to feel good about technically obeying the rules, without actually doing anything that would cost you anything.

Some people are very good at finding loopholes, especially children. Tell your son or daughter that they are not allowed to have the cookies in the cabinet after school, and they will find cookies someplace else and consume them. “You didn’t say I could not have cookies,” your little sweetheart will say, “you just said I could not have the ones in the cabinet.” You say, “You know what I meant. Next time…” Yes, you have been bested.

When a youth group member comes to me and asks to go to the bathroom, I sometimes need to say, “Yes, you may go to bathroom here on the lower level, right down that hall and when you are done you must come right back.” If not, I may be giving them permission to go to the upstairs bathroom where they might decide to interrupt the children’s ministry.

At times, we try to find loopholes in our life of faith as well. We look for ways we can be obedient that will not require much of us. Jesus does not let us get away with tacit obedience to a handful of rules. He calls us instead to reorient our lives.

The need for context

Welcome to week 7 of our series called The Rule of Life where we are looking at Jesus’s “Sermon on the Mount.” I want to reiterate what I said a couple of weeks ago. One of the great challenges for Bob and I as we do this series is to not take the Sermon on the Mount apart. It is tempting to take this as a series of proverb-like statements and stories that we can then expound upon out of context. This, like any time one takes a piece while ignoring the whole, is dangerous work. Whenever we take quotes out of scripture without looking at the entirety, we may come up with something that is quite the opposite of what was originally intended.. When we do that, we run the danger of supporting something we do not intend.

So when we come to these verses, specifically about divorce, we hear something that doesn’t seem to fit what we know about Jesus in the rest of the New Testament, and we have heard these verses used to manipulate and hurt people. So what do we do with these verses?

Someone once said, “A text without context is just a pretext for whatever we want it to say.” So we need some context. Throughout this morning’s sermon, I will share several techniques for reading scripture that may be helpful.

Technique 1: Immediate context

The first helpful technique is to look at the context the author gives in the verses around this one and ask how this fits into the rest of the story that surrounds it. To do that we need to pull back to wider shot of this section.

In our passage for this morning we need to look at the whole Sermon on the Mount. When we do, we find at the beginning of this section a group of verses that serve as a type of prologue to this passage – Matthew 5:17-20. Jesus begins this prologue by saying:

Do not think that I have come to abolish the law or the prophets; I have come not to abolish but to fulfill. For truly I tell you, until heaven and earth pass away, not one letter, not one stroke of a letter, will pass from the law until all is accomplished. (Matthew 5:17-18).

Jesus clearly states he is not putting forth a new set of laws. These are not be understood, as the Sermon on the Mount is sometimes referred to, as the Christian Ten Commandments. I believe Jesus would have been offended by that implication. The Law in what we call the Old Testament, was perfectly given by God on Mount Sinai and recorded in Exodus 20. Jesus is not correcting the “old law” as thought it were inadequate, nor is he imposing a new law. Jesus clearly says in this passage that he is not abolishing but fulfilling the law.

So what is he doing here? At the end of this prologue, verse 20, Jesus says what it is about in a sentence that strikes my ears as a bit odd:

For I tell you, unless your righteousness exceed that of the scribes and Pharisees, you will never enter the kingdom of heaven” (Matthew 5:20).

Throughout the gospels the scribes and the Pharisees are criticized by Jesus for their sense of “self-righteousness.” How could our righteousness exceed that of these legal gurus? Does Jesus really want us to out-do the Pharisees and scribes at their own game? If not, what in the world does Jesus mean?

Technique 2 – Author context

That brings me to Bible-reading technique two. We need some clues to understand this statement. To do that we look elsewhere in the book we are reading for clues about what this could mean.

Because I want to be true to not only what Jesus is saying, but also to what Matthew is trying to communicate, I want to stay in Matthew. Remember that originally Matthew was not part of a bound collection of biographies of Jesus, but stood alone. So our best clues will come from within the book we are looking at (or others by this same author if that applies), and not something from somewhere else in the Bible at this stage.

If we turn to a passage much later in Matthew’s story, Matthew 23, we get a clue as to what Jesus means by a righteousness that exceeds that of the scribes and Pharisees. In Matthew 23 we hear Jesus ripping the religion of the scribes and Pharisees in a passage that is sometimes called the “Seven Woes.”

They are called the “Seven Woes” because seven times Jesus uses the word “woe” before giving a scathing remark. Six begin with Jesus saying, “Woe to you, scribes and Pharisees, hypocrites [which should probably would be better translated “actors”]!” The other one begins with “woe to you blind guides” but the implication is certainly that it is also directed at the scribes and Pharisees, as in the other woes he sometimes calls them blind guides.

In verses 23 and following, we get a clue that informs today’s passage when Jesus says:

“Woe to you, scribes and Pharisees, hypocrites! For you tithe mint, dill, and cummin, and have neglected the weightier matters of the law: justice and mercy and faith. It is these you ought to have practiced without neglecting the others. You blind guides! You strain out a gnat but swallow a camel!” (Matthew 5:23f)

I don’t know if you picked up on it, but that is supposed to be funny. Jesus uses humorous images to make his point. First, he paints a picture of the scribes and Pharisees going through their spice rack at the end of the week to grab 10% of each spice to give. Second, he pictures them straining out a gnat – commonly considered the smallest animal by Jesus’s contemporaries – but swallowing a camel – commonly understood as the largest animal. It is similar to us saying, “you pick off ants but swallow an elephant.” He is accusing the scribes and Pharisees of missing the forest for the trees.

Between those images we find our clue about what he means back in 5:20 that our righteousness must exceed that of the scribes and Pharisees to enter the kingdom of heaven. He says that these religious leaders have “neglected the weightier matters of the law: justice and mercy and faith. It is these you ought to have practiced without neglecting the others.” There is the exceeding – exercising justice, mercy, and faith as one keeps the Law.

Justice and mercy take me back to the Beatitudes, the “preamble” (as Pastor Bob has called it), of the Sermon on the Mount. There Jesus says, “Blessed are those who hunger and thirst after righteousness” which is better translated “justice”; and “blessed are the merciful.” A picture is starting to emerge. This morning’s passage is talk about exceeding the law with justice, mercy, and faith as hinted at in the Beatitudes.

Like Calvin, we sometimes look for loopholes – ways to obey the letter of the law and justify ourselves without requiring much change or investment from us. We want to obey God without being inconvenienced. What is the least I can do. Justice, mercy, and faith, on the other hand, require something from us – a change of heart, a change of attitude, a change of focus.

So let’s dig into the specifics of this passage with new eyes that understand that Jesus is pushing his hearers from minimal obedience to the law, toward living the law with justice, mercy, and faith.

It has been said… But I say…

Following the prologue in Matthew 5:17-20 is a section of the Sermon on the Mount that follows a pattern Bob introduced in his sermon on last week’s passage. The pattern continues through this week’s passage, and will conclude  in next week’s passage at the end of chapter 5.

The pattern starts with says something like, “You have heard that it was said…” and then shares a point in the Law, usually one of the 10 Commandments. He follows that up with something like, “But I say to you…” and gives what many people hear as a stricter interpretation of that Law. But don’t go there. That is not what Jesus is doing here. Remember, he is not offering a new law. As we just showed, each of these is instead an illustration of righteousness EXCEEDING that of the scribes and Pharisees – through justice and mercy and faith.

To get started let’s take a quick look at the passage Bob preached on last week. Jesus says, “You have heard that it was said to those of ancient times, ‘You shall not murder’; and ‘whoever murders shall be liable to judgment.’ But I say to you that if you are angry with a brother or sister, you will be liable to judgment” (Matthew 5:21-22). Jesus takes the commandment about murder, and turns it to talk about anger.

It is as if Jesus is saying, “Hey, do you think you are OK with God because you haven’t killed anyone? Well, don’t be so smug. If you have been angry and lashed out at another (which I would imagine we all have done), you have sinned because that is not an act of justice or mercy or faith.”Â  He takes a Law we can follow without a whole lot of effort, change, or investment on our part, and reminds us that is not enough. We have often broken this law by not obeying the justice and mercy behind it.

Adultery and Lust

Next Jesus follows the pattern to address adultery: “You have heard that it was said, ‘You shall not commit adultery’” (Matthew 5:27) – one of the ten commandments. Most can feel pretty confident they have been obedient. Then Jesus clarifies using the measuring stick of justice and mercy. He says, in my words, “Hey, if you think you are OK in the eyes of God because you haven’t committed the physical act of adultery, look out. Without the act, you have broken the intent of God’s law every time you have looked lustfully at a woman.”

It does specifically say “woman” – I looked it up. The Greek word is a form of gune, the root of our word gynecology. This is directed at the guys. Not to say that women don’t have an issue with lust, but for the guys it is far more prevalent.

I have read statistics that say as many as 50% of males over age 18 have an issue with pornography. In fact, most listings of the top addictions in our country will have an addiction to porn or sex as the number 2 addiction after alcohol. I want to encourage any of the guys here who have that secret account on their laptop that streams those movies, or whose greatest embarrassment would be to have us put their web-browsing history up on the screen, to find a way to cut that out of their lives. That’s what I think Jesus is talking about when he says to pluck out your eye or cut off your hand. Get that out of your life. Find an accountability partner. Get that software that sends your browsing history to someone you trust. Get this addiction out of the dark and into the light. Do not continue to allow this addiction to control you. If you need help with that, please email me and I will put you in touch with the right people to help with that. OK?

For those who don’t have that issue, let’s get back to understanding this in the broader context of what Jesus is saying. Lust objectifies and dehumanizes the other. The one being lusted after ceases to be a person in our eyes, and become a collection of body parts. The justice and mercy issue is to see every person as a sister or brother in Christ – a full human being. When we see people with justice and mercy we treat them better, we look out for their needs, or to put it quite simply – we care about what happens to them.


Jesus then goes on to talk about divorce and says,

“It was also said, ‘Whoever divorces his wife, let him give her a certificate of divorce.’ But I say to you that anyone who divorces his wife, except on the ground of unchastity, causes her to commit adultery; and whoever marries a divorced woman commits adultery” (Matthew 5:31-32).

Technique 3: Historical context

This is the biggie today that people have questions about. Here is another Bible reading technique that you should employ – historical context. Here is some of what we know about divorce in Jesus’ day.

According to the Law of Moses in Deuteronomy 24:1-4, it was acceptable for a man to divorce his wife, as long as he gave her a certificate of divorce. This was intended to be a protection for the women, but in the time of Jesus was being interpreted as you could divorce for any reason, so long as you gave the certificate of divorce. By that understanding a husband (and it was only the husbands) could decide one morning he wanted to divorce his wife because she burned the toast for breakfast. That was considered by many to be acceptable if he gave her a “certificate of divorce.” He had obeyed the law and was “good” in the eyes of the Temple and, by extension, God.

Divorce, as you can probably imagine, was devastating to women in the first century. They could not, for the most part, honorably support themselves on their own. In the patriarchal culture of the day, women needed a man in their lives to support them financially. A divorce was almost certainly a life-sentence of crushing poverty for the woman.

So Jesus says to the men (again, my words), “Don’t think it is OK to devastate a woman in your life because you do it in the “right way.” Your action of divorce isn’t just about you, but is also about her. Think about the consequences to her, not to mention the children, extended family, and everyone else involved.” I’m sure you hear the justice and mercy in this statement.

Jesus goes on to say a couple of things that in my opinion have been misused for a very long time. One, he says that the only reason to get divorced is infidelity/adultery. Then, secondly, he says anyone who marries a divorced woman commits adultery (Matthew 5:32). What do we do with these verses?

For a detailed understanding of this passage and its parallel in Matthew 19 (which I do not have time to work through today), I have had placed in your bulletin an article from John Ortberg that gives a different way of looking at this passage that I think is valuable. Jesus may be addressing a much larger conversation in the culture of his day than this scripture gives us insight into, and I offer the handout especially to those who struggle with the fact of their divorce and/or remarriage.

But there are a couple of things I can say here:

First, recognize that in the previous section Jesus used a literary technique known as hyperbole to make his point. No sane person reads Jesus’s words of self-mutilation – plucking out your eye or cutting off your hand if they cause you to sin – literally. All can agree this is hyperbole.

Knowing that, we must at least consider that Jesus is using the same technique in the passage about divorce. When he says the ONLY acceptable reason for divorce is infidelity, that might also be hyperbole. And when he says that marriage to a divorced person constitutes adultery, that too may be hyperbole.

Based on the evidence I see in this congregation alone, I have to lean that way. There are many whose second marriage after a divorce is an incredible blessing. Their first marriage was a mess, but the second one is godly and they are growing together in Christ. All the evidence seems to point to the fact that God is blessing this 2nd marriage and doesn’t see it as something outside of his will. We need to take that evidence seriously.

Remember this is an issue of adding justice, mercy, and faith to the law. So, by extension, let me say this as clearly as I can:

If you are being hurt in your marriage, it is not a sin for you to get out. If you are being physically or emotionally harmed, it is not the “right thing to do” to allow another to treat you that way. Protect yourself. Get out.

I was talking to a counselor this week who said this verse is sometimes used by husbands to keep their wives in the home and prevent them from filing for divorce. While they continue to inflict abuse, they quote this verse saying that they have not committed adultery. Do not let that happen to you. Jesus does not what you to subject yourself to physical or psychological violence. That is not what this verse is about.

But don’t take this as an excuse for an “any reason” divorce. If Jesus is using hyperbole here, he is also saying that we need to take our marriages seriously. If your marriage is going through a rough spot, it is not OK to bail. It may be legal, but it is not right. We need to exhaust every possible means of reconciliation (short of getting hurt) before we walk away.

It appears that some today do not work hard enough to save their marriage. They get bored, or life gets rough, or they think they can do better, or they find someone who makes them feel good in the moment – and they are quick to dissolve a commitment they made “until death do us part.” We need to take our marriage commitments must more seriously, which includes the lust bit in the first part above.

Finally, I think it is also implied in all this passage that when divorce happens, we need to treat our ex-spouse with justice and mercy and faith. I am surprised to hear stories about men and women who after a divorce want nothing to do with their former partner. Men who don’t pay the alimony and child support until the courts get involved, that is wrong. Women who withhold visitation with the children until they are forced to do so, that is wrong. Even in divorce we need to continue to treat one another with justice and mercy and faith.


Finally for today, Jesus turns his attention to oaths and I need to be very brief here.

Jesus follows the patters, “Again, you have heard that it was said to those of ancient times, ‘You shall not swear falsely, but carry out the vows you have made to the Lord” (Matthew 5:33f). The interpretation of this became that if you “swore to God” you would do something, you had better do it, but if you swore by something else, you could break the oath. So people created a loophole by swearing by other things – Jesus mentions heaven, earth, or your own head. It appears that was the equivalent of crossing your fingers behind your back on the grade school playground.

Jesus says, “Really? You think this makes a difference?” His exact words were, “But I say to you, Do not swear at all” (Matthew 5:33f). “Let your words be ‘Yes, Yes’ or ‘No, No’” (Matthew 5:37). He calls us to exceed the letter of the law by being people of our word. Doing what we say we will do, and saying No to that which we will not do.

Again it comes down to respect – or Jesus might say justice and mercy and faith. Don’t take advantage of the other, or try to pull something over on them by crossing your fingers when you make a promise. Take the promise seriously. Put yourself in their shoes. Honor your oath by doing what you are expected to do.

These three passages are related. They all deal with our selfishness.

Lust and adultery are selfish. When we look at another as simply an object of desire, whether or not we go through with the act, we are thinking only about ourselves and not about the other as a person of God.

Divorce for a bad reason is selfish. You hear these kinds of things all the time when it comes to divorce. “I am just not in love anymore”; “things aren’t what they used to be for me”; or “I feel like we have grown apart.” There are spouses, kids, parents, friends, and lots of other people involved in a marriage and you need to work hard to keep that oath and not be selfish.

Breaking an oath is selfish. We just don’t want to do it anymore and so we look for a loophole to walk away. Follow through. The other is counting on you.

Don’t be selfish. Treat others with justice and mercy and faith.


I need to offer one last piece. Maybe you hear these verses and you think, “Man, I have messed up pretty bad.” Maybe you have had an affair, struggle with pornography, have used loopholes to get out of business contracts, or maybe you walked away from a marriage without really trying.

Technique 4: Biblical context

I want to offer you a story – one of my favorites. It comes from John 4 – based on the techniques I have been telling you about, not the best text because it is outside of Matthew, but I think is extremely relevant.

It is noon and Jesus and his disciples stop in a little town named Sychar. The disciples go off to buy lunch while Jesus, exhausted from the journey, decides to take some alone time. He sits down by a well that had been dug by Jacob, one of the people by whom God identifies himself in the Old Testament – the God of Abraham, Isaac, and Jacob.

A woman comes to draw water. Odd that she would come at noon, the heat of the day. Most of the women came nearer to sunrise in the morning and sunset in the evening, enjoying the shade of their homes in the brightest part of the day. She probably does this to avoid the rest of the women in town.

We learn later that she is divorced. In fact, she has been married five times and is currently living with a guy who is not her husband. Sounds like she has a history of divorce, and lust, and maybe even breaking oaths.

Head down, I imagine, she goes about her business of drawing water from the well. Jesus doesn’t avoid her. Rather, he strikes up a conversation with her, probably for the sole purpose of drawing her out. In the process he offers her “living water,” what we might call “salvation” or “a living relationship with God through Jesus Christ.”

Then something remarkable happens that is often missed (John 4:25-26):

The woman said to him, “I know that Messiah is coming”…”When he comes he will proclaim all things to us.” Jesus said to her, “I am he, the one who is speaking to you.

This is the first and clearest statement Jesus makes in the Gospel of John declaring himself to be the messiah. He fully reveals himself to her.

I just want those of you who feel so out of it to recognize that you are not outside of the love of Jesus because of mistakes that you have made. He is still here for you. Ready to show you who he is, and to welcome you into the fold.

As we go forth from this place, may we not be just “keepers of the law,” looking for loopholes that make it easy to obey. May we instead go above and beyond the letter of the law, exceeding the righteousness of the scribes and Pharisees by being people of justice and mercy and faith with our family, our friends, our classmates and coworkers, and anyone else we share the world with.


Unless otherwise noted, all quotations of Scripture are from the New Revised Standard Version available online at

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