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Biblical/Doctrinal Studies:
Walking That Extra Mile: A Slightly Different Twist on Matthew 5:38-48
by Ed Vasicek

I can honestly say that I have been "working" on the above verses for approximately 25 years in the back of my mind. Even while a student at Moody Bible Institute, I kept my eyes open to comments or insights that could help me understand these verses.

The problem with the above verses (if understood apart from the context I will mention below) is simple: they fly in the face of BOTH Old Testament teaching, the latter teachings of Christ, and the Epistles. I am not going to elaborate about these differences here, but Lewis Sperry Chafer does a thorough job of this in his book titled, Grace, The Glorious Theme.  Although I do not agree with Chafer's solution to the conflict between the Sermon on the Mount and the latter teachings of Christ and the Apostles, he at least acknowledges the reality of the conflict.

Of course I believe the conflict disappears when we do what good interpreters are SUPPOSED to do, namely answer these two questions: (1) How did the speaker/writer understand his own words? and (2) How would the original audience have understood these words? 

In light of this, I would like to go into the text with these pre-existing convictions:

  1. What Christ taught did NOT contradict the Law nor the Epistles.
  2. The Law is not some evil entity for childish disciples but is truly the Word of God and, though incomplete, is as pure as the One Who gave it.
  3. Christ did not come to destroy, put down, or devastate the Law, but to fulfill it (properly interpret it).
  4. The Law of Moses was not given to mankind, but to Israel; the Covenant of Noah WAS given for all mankind.
  5. When Christ quotes the OT passage upon which He is commenting, fine; but when He doesn't, it might help to infer the passage and go from there. Since we have perhaps 10% of all that Christ said in this sermon, and since the Sermon on the Mount is a commentary and application of the Law, deducing the texts in question can prove invaluable, though risky.

I have pasted below a bulletin insert I wrote which offers additional thoughts to contemplate:

Jewish Insights Upon the Sermon on the Mount

As I mentioned before, our version of the "Sermon on the Mount" consists of sermon highlights; the actual sermon itself probably lasted two hours. We have perhaps only a dozen "highlight" minutes from which to reconstruct its meaning.

Since Christianity eventually abandoned its Jewish roots, and since gentile believers eventually outnumbered (and later suppressed) Jewish believers, the key to interpreting this sermon was lost. It is only when we remember that the speaker and audience were Jews and that Christ was addressing the hot issues and controversies of the day (including applying the Old Testament Law in light of current circumstances) that the sermon falls in line (not only with the Old Testament but the New Testament epistles as well).

For example, Israel was then under Roman occupation. A Roman solider could legally constrain any non-Roman to carry his supplies for one mile. When Christ speaks of going two miles, He is talking about voluntarily going beyond the requirement of the Roman law. Yet Christ does not say, "as many miles as someone wants." So he encourages us to offer generous but reasonable boundaries.

It is also interesting to note the understanding of the Jews regarding the OT command, "an eye for an eye" in the first century. David Stern comments about how Jews in the first century probably understood this command:

....eye for eye, etc. shows that God was not commanding revenge, but controlling and limiting it. Retribution and punishment must be commensurate with the crime; contrast Cain and Lamech's extraction of multiplied vengeance at Genesis 4:24....

Stern then quotes from an ancient Jewish source, the Mishna, to show that the Jews did not understand "an eye for an eye" literally. Here is the Mishnah quotation:

If anyone wounds his fellow, he becomes liable to compensate the injured party for five different aspects of the injury: damage, pain, healing, loss of time from work, and insult....

Note that the Jews were required to compensate those they insulted.  In ancient Jewish culture (and other cultures, even today), a slap in the face was considered the prime example of a great insult. (We talk about "receiving a slap in the face" or "kick in the pants.")  When Christ is talking about turning the other cheek, He is not addressing the issue of self-defense in general, nor national policy, but He is addressing a debate of the day, namely, did the "eye for eye" command apply to being insulted? Christ made it very clear that individual believers who are insulted for His Kingdom must bear it. Indeed, not availing ourselves of all our rights may provide opportunities for others to see that we are not out to exploit others, that Christians are more concerned with doing right before God than we are with "getting ahead." We are not out to get all the "gusto" we can, but to glorify God.


Here are a few additional thoughts not in the paper. David Daube in his work, The New Testament and Rabbinic Judaism (Hendrickson) devotes a chapter entitled, "Eye for Eye" to discuss the Jewish understanding of Talion (the law of retribution), the subject of the Jewish understanding of the "Eye for Eye" command. To the first century Jew, that expression was more or less synonymous with the idea of financial compensation and litigation. This sets the entire tone for verses 38-42—litigation.  Turning the other cheek, etc., connects to litigation. The only issue that is not about litigation is that of walking the extra mile, which is encapsulated within litigation issues because the principle of walking the extra mile is also the attitude we should take in matters of litigation.

Here is my sermon outline proper:

Walking That Extra Mile (Matthew 5:38-48)


  1. If you have old computer disks from an Apple II computer, they will not work on a Windows based unit without conversion.
  2. Why? Two different operating systems.
  3. Christ demands His followers operate under a different operating system than society at large: a different way of thinking with different values and a different lifestyle.
  4. You must be willing to be different and sometimes radical in the eyes of the world.

MAIN THOUGHT: Being A Disciple of Christ means operating our minds with a different program than most of society, motivated by our relationship with Christ.

That program can be defined by three rules by which to play the game of life.

I. Being Generous With Grace (38-42)
Vs. 38 sets the tone: the matter at hand is litigation and compensation.

  1. Accepting Insults (39)

    The issue here is NOT self-defense, passivity, or non-confrontation. Christ encourages us to confront those who offend us.  The issue is taking an INSULT.

    In almost every culture, the ultimate insult is a slap in the face. At debate in the first century was that fifth point of compensation, namely, for insult. We already noted that quotation from the Mishnah:

    If anyone wounds his fellow, he becomes liable to compensate the injured party for five different aspects of the injury: damage, pain, healing, loss of time from work, and insult....

    Jesus obviously disagreed with this trend (according to Daube, it was being debated in the first century and then solidified into the Mishnah in the 2nd century).

    Jesus was saying "take the insult and ask for more." This is in contrast to the latter Rabbinic ruling in the Talmud:

    "Does he give him a blow upon the cheek? Let him give two hundred zuzees; if with the other hand, let him give four hundred."

    (Bara Kama, cap. 8, hal. 6—quoted by John Lightfoot)

    In contrast to suing a brother for every possible infringement, Christ is saying, "give people space." This has a pragmatic effect, reconciliation (see Proverbs 15:1, "A soft answer turns away wrath."), and it is also WALKING THE EXTRA MILE, giving people the benefit of the doubt.

    Please note Christ is not talking about stabs to the chest, punches to the nose, nor twenty slaps on the cheek. Please pay attention to the MODERATION of this section. You turn the other check for a second slap—but it ENDS there.

    You walk the extra mile, but not an unlimited amount of miles. Once you perceive the absolute moderation of what Jesus is talking about, you realize that things like pacifism are not even being contemplated.

    Jesus is saying, "put up with insult and even a moderate amount of abuse before you take someone to court. Let people have space to be human, to err. Do not take the attitude of an opportunist, perched to exploit every infraction."

  2. Avoiding Litigation

    Again, the main theme of litigation comes into play. Here an example is placed before us; once again, the example is strikingly MODERATE.  A person is wanting to sue another for a tunic. Perhaps there is some disagreement or dispute over a matter, a damage, etc. Rather than go to court, it is better to take loss and settle out of court. This is related to 5:25, so please compare it.

    Rather than fight over ones claim to a tunic (as compensation), the Christian should give it to him (and ones coat as well) if that would preclude litigation.

    It is interesting to note that Christ did not use the example of a house or fortune. Although clothing in the ancient world was more of a commodity back then, the concession is still not THAT major. Better to take a moderate loss and stay on good terms with others than prove your point or win your case. If you won't schmooze, you lose.

    Again, the principle is WALK THE EXTRA MILE, not letting people abuse and exploit us.

  3. Going Beyond Obligation

    I have dealt with the Roman Law and the ability of a Roman solider to constrain any non-citizen to walk one Roman mile (1,000 paces), carrying his supplies. Christ says go beyond—walk two miles.

    Again, the attitude is that of being gracious, going BEYOND what is REQUIRED.  Once again, note the moderation. The text does not say, "Go as many miles as he wants you to go." Christ is exhorting us to an attitude of service, grace, letting people have space, and generosity. But NOT to the extreme. There is still plenty of space for tough love, not being exploited, knowing how to set boundaries.

    If you think about it, Christ IS advocating setting boundaries. But He does not want us to be concerned about others going over the line as much as he does those who CLEARLY go indisputably way over that line. We give others the benefit of the doubt, but we have our limits.

  4. Practicing Responsible Generosity

    I believe the part of the Law Christ was addressing was Deuteronomy 15:9-11:

    Be careful not to harbor this wicked thought: "The seventh year, the year for canceling debts, is near," so that you do not show ill will toward your needy brother and give him nothing. He may then appeal to the LORD against you, and you will be found guilty of sin. Give generously to him and do so without a grudging heart; then because of this the LORD your God will bless you in all your work and in everything you put your hand to. There will always be poor people in the land. Therefore I command you to be openhanded toward your brothers and toward the poor and needy in your land.

    Christ was not talking about giving handouts to every stranger or pan-handler around. He was saying that we do have a responsibility to loan money or offer help to responsible people (destitute because of circumstances beyond their control) we know whether we will be paid back or not.

    Whether "asking" and "borrowing" are merely parallel terms or not is a matter of debate. We should feel under no obligation to give money to anyone who asks us for handouts. If you thought otherwise, a five minute trip to Chicago would find you completely cleaned out.

    Remember, Christ spoke at great lengths about these matters, we have only sermon highlights. Do not confuse truth with whole truth.

    If I am right, that Christ was addressing Deuteronomy 15, then we can see what was at issue: not the worthiness of the destitute person; it is assumed that he is worthy; what is at stake is the uncertainty of being paid back. Folk wisdom is true: do not loan out money you cannot do without. On the positive side, we cannot let responsible people we know go hungry.

II. Being Stingy With Hatred (43-48)

  1. Hatred and love can co-exist—see Psalm 5:5—a time to love and a time to hate

    Based on Psalm 5:5 and other texts, God both hates (is angry at, has wrath stored up toward) sinners and yet loves them (John 3:16).

  2. Loving an enemy means choosing to let our love OVERRIDE our feelings of disgust.

    Not all forms of love are the same. The secret is NOT the Greek word, but the context

  3. This love is in the form of duty, not feeling
    1. note vs. 45
    2. Exodus 23:4-5
    3. Romans 12:18-21

    We do not love our enemy the same way we love God, our spouse, our children, our brethren, or our neighbor.

  4. Love includes greeting others (46-47)
    1. important way to show love; we must change habits
    2. including new people (not just greeting our friends.)

    It is great to have a circle of friends; it is horrendous to never include others or expand ones relationships; Greeting people is IMPORTANT and crucial toward LOVING PEOPLE. Let me say it again: if you don't schmooze, you (and they) lose.

III. Valuing Godliness Above Earthly Status (48)

  1. Even though none of us CAN be perfect, that should still be our aim.
  2. Bow and Arrow—can't always hit bull's eye, but can try
  3. Our models, icons, and heroes influence us more than we think
  4. Television sets the "status"—causing great financial stresses.
  5. Aiming to be like God, not some upper middle class singles on TV

You can aim for designer clothes, a house in that exclusive neighborhood, that brand of car which shouts, "prestige" or you can aim to be like God. You cannot aim at both.


  1. You cannot follow Christ and use society's operating system.
  2. You cannot be out to take advantage of or regulate others.
  3. Christ calls you to be generous with grace, stingy with hatred, and to aim at the right target: knowing God and being godly.

You may also like to see Interpreting the Sermon on the Mount: Special Considerations as well as A Hermeneutical Procedure To Best Interpret The Sermon on the Mount.

Pastor Ed

Reprinted from the February 2002 Body Builder, a publication of Highland Park Church.

Highland Park Church   516 W. Sycamore St. Kokomo, Indiana, 46901 USA   (765)452-1779    church@highlandpc.com    Main Service: Sun 10:30 a.m.