Legalism does not work. It never has and it never will. Legalism is the pursuit of good works — obedience to God’s law and the ethical commands of the Bible (and beyond) — abstracted from faith in Christ in order to be acceptable before God. The legalist approaches the Bible as a law-centered document rather than a Christ-centered one. Legalism attempts to domesticate the law of God and exacerbates sin rather than killing it because it feeds the flesh.

Legalism always produces two kinds of people: Those who know they do not measure up to God’s standards; and those who pretend that they measure up to God’s standards. I have often asked people, “What are your personal standards for what a person should say and do? Have you, in every instance, lived up to your own standards?” The answer is always no. If we haven’t lived up to our own standards, then we can be certain we have not lived up to God’s standards either.

The problem with the righteousness of the Scribes and Pharisees

The Sermon on the Mount turns on Matthew 5:20: “For I tell you, unless your righteousness exceeds that of the scribes and Pharisees, you will never enter the kingdom of heaven.” Jesus’s assertion would have been startling to his hearers. Who could enter the kingdom of heaven then? The hearers would have been wondering: “How can anyone have better righteousness than those experts in the law?” At the end of the next section (Matt. 5:21-48), Jesus clarifies, “You therefore must be perfect, as your heavenly Father is perfect” (Matt. 5:48).

In Matthew 5:21–48, there are six sections addressing various examples of the better righteousness: (1) murder (5:21–26); (2) adultery (5:27–30); (3) divorce (5:31–32); (4) oaths (5:33–37); (5) vengeance (5:38–42); and (6) love of enemies (5:43–48). Each of these begins “You have heard that it was said” (vv. 21, 27, 31, 33, 38, 43), and then “But I say to you …” (vv. 22, 28, 32, 34, 39, 44).

Jesus’s teaching in this section is often described as “antitheses,” but that is a poor description of his instruction. After all, Jesus had already clarified, “Do not think that I have come to abolish the Law or the Prophets; I have not come to abolish them but to fulfill them” (Matt. 5:17).

A close reading of this section reveals three common words and phrases that Jesus uses throughout this section. These three formulas hint at Jesus’s primary takeaway for his disciples:

  1. The gospel according to the legalist: “You have heard that it was said”

Using this phrase, Jesus refers to a particular Old Testament law and exposes the way a legalist would wrongly interpret and apply the command.

  1. The gospel according to Jesus: “…But I say to you”

Next, Jesus explains the way the law is rightly to be understood and applied in light of deeper kingdom dynamics because, in him, the kingdom of heaven was at hand.

  1. Don’t pit Old Testament vs. New Testament: “If,” “so,” or “then”

Jesus also, with one exception, provides examples of how one could take steps that would demonstrate the obedience of faith — the better righteousness.

Some wrongly pit the Old Testament against the New Testament, asserting that the OT is law-focused and external while the NT is heart-focused and internal. Even a cursory reading of the OT makes clear that true righteousness always involved internal faith and a transformed heart.

You shall love the LORD your God with all your heart and with all your soul and with all your might. And these words that I command you today shall be on your heart (Deut. 6:5-7).

Rend your hearts and not your garments (Joel 2:13).

The legalist abstracts the biblical command from the canonical gospel narrative. Thus, according to the legalist, if you have not murdered, committed adultery, and have not given a deceptive oath, then you are righteous; if you have, then you are unrighteous. The legalist also concludes, since they are righteous, they have a right to give a certificate of divorce, administer vengeance, and hate their enemies. Their focus is on the self.

The citizen of the kingdom of heaven hears the commands of God as embedded in the biblical gospel narrative. This is why the beatitudes do not make sense to the legalist but they do make sense to kingdom citizens. The Bible is not law-centered (another way of saying man-centered), but it is Christ-centered and gospel-focused.

Contrasting patterns of thought

Consider below and contrast the pattern of thinking of the legalist and the kingdom citizen. They can read the same laws and come to opposite conclusions because they have opposing starting points. The fundamental issue with Jesus’ six examples in Matthew 5:21-48 is that they are not abstractions, they exhibit the way kingdom ethics work. The examples should be considered as a part of the same gospel cloth and not as independent abstract commands.

The pathway of legalistic thinking is:

  1. Me
  2. The law
  3. Their righteousness
  4. How much their righteousness will please God and others

The pattern of the kingdom citizen’s thinking is:

  1. God in Christ.
  2. Christ’s righteousness and law-keeping for me.
  3. Others.
  4. How can I serve God in Christ and others by rendering the obedience of faith?

With the first way of thinking, a legalistic approach to applying the “You have heard it said” commands make sense, yet Jesus’s responses (“But I say to you”) do not. The kingdom citizen reverses the focus, trusts in Christ’s righteousness, and walks in line with the gospel.