Charles Simeon writes...

THE explanation which our Lord has given us of the sixth commandment, shews, that we are not to confine the import of the commandments to the mere letter of them, but to regard them as extending to the words of our lips, and the dispositions of our hearts. Nor must we imagine that they are intended solely to prohibit sin: they must be understood as inculcating all those virtues which are opposed to the sin forbidden. This is evident from the connexion in which our text stands with the preceding context. Our blessed Lord had declared, that a wrathful word was in fact a species and degree of murder: and from thence he takes occasion to inculcate the necessity of exercising in every respect a spirit of love, so as, not only to entertain no anger in one’s own heart against others, but so as not to leave room for the exercise of it in the hearts of others towards us. The direction which he gives us respecting it will lead us to shew,

I. The duty of seeking reconciliation with men— Wild beasts are scarcely more prone to injure their own species, than man is to oppress and injure his fellow-man. Indeed, considering what tempers we have, and what tempers exist in others, and what frequent occasions of interference with each other must of necessity arise, it would be a miracle if any of us had so conducted himself on all occasions, that no brother should on any account “have ought against him.” We apprehend that no one who knows any thing of his own heart, would profess himself so perfect, as never to have done towards another any thing differently from what he would have wished to be done towards himself. Supposing then that “a brother have ought against us,” what is to be done? I answer, 1. We should be willing to see our fault...2. We should be ready to ask pardon for it...3. We should be desirous to make reparation for it....Such is our duty towards an offended brother.  (Read the entire sermon - Matthew 5:23,24 The Necessity of Seeking Reconciliation with Men - Goto Page 119)

The setting is worship in the Temple in Jerusalem (or church in our day).

Offering (1435) (prosphero from prós = to, toward + phéro = bring - see Offering, Offerings) means to carry or bring something into the presence of someone usually implying a transfer of something to that person. Here it refers to an offering that can include gifts, prayers, or sacrifices.

Prosphero - 47x in 45v - Mt 2:11; 4:24; 5:23f; 8:4, 16; 9:2, 32; 12:22; 14:35; 17:16; 18:24; 19:13; 22:19; 25:20; Mk 1:44; 2:4; 10:13; Luke 5:14; 18:15; 23:14, 36; John 16:2; 19:29; Acts 7:42; 8:18; 21:26; Heb 5:1, 3, 7; 8:3f; 9:7, 9, 14, 25, 28; 10:1f, 8, 11f; 11:4, 17; 12:7. NAS renders prosphero = bringing to(3), brought(2), brought to(8), brought up to(1), deals with(1), get to(1),make an offering(1), offer(8), offered(12), offering(4), offers(1), present(2), presented(1), presenting(1).

Altar (2379) (thusiasterion from thusia = that which is offered as a sacrifice - see Altar) refers to any type of altar or object where gifts may be placed and ritual observances carried out in honor of supernatural beings. In the NT thusiasterion is employed to refer to a number of different types of altars, including the altar for burnt offerings in the Temple, the altar of incense, the altar which Abraham built, and the heavenly altar mentioned in the book of Revelation.

Thusiasterion - 23x in 21v - Matt 5:23f; 23:18ff, 35; Luke 1:11; 11:51; Rom 11:3; 1 Cor 9:13; 10:18; Heb 7:13; 13:10; Jas 2:21; Rev 6:9; 8:3, 5; 9:13; 11:1; 14:18; 16:7

In the present context "the altar" refers to the one in the inner court of the Temple in Jerusalem. There amidst a background of solemn worship, the worshiper experiences recollection of a brother with something against him (see Mark 11:25) and Jesus says this should  prompt immediate efforts to be reconciled for only then is formal worship acceptable. 

One wonders how many in church each Sunday would be well advised to pay heed to Jesus' instruction in this passage? What would our worship services look like if this principle were diligently practiced (under grace not law)?

The principle is obedience begets genuine worship as Samuel recorded in his address to the disobedient King Saul who had offered to the Lord sacrifices that were to have been destroyed...

And Samuel said, "Has the LORD as much delight in burnt offerings and sacrifices As in obeying the voice of the LORD? Behold, to obey is better than sacrifice, and to heed than the fat of rams. (1 Samuel 15:22)

In Psalm 51 apparently motivated by David's sins of adultery and murder records a similar train of thought...

For Thou dost not delight in sacrifice, otherwise I would give it; Thou art not pleased with burnt offering. The sacrifices of God are a broken spirit; A broken and a contrite heart, O God, Thou wilt not despise. (Psalm 51:16-17) (Spurgeon's comments - Verse 16; Verse 17) Spurgeon on verse 17 - The sacrifices of God are a broken spirit. All sacrifices are presented to thee in one, by the man whose broken heart presents the Saviour's merit to thee. When the heart mourns for sin, thou art better pleased than when the bullock bleeds beneath the axe. "A broken heart" is an expression implying deep sorrow, embittering the very life; it carries in it the idea of all but killing anguish in that region which is so vital as to be the very source of life. So excellent is a spirit humbled and mourning for sin, that it is not only a sacrifice, but it has a plurality of excellences, and is preeminently God's sacrifices. A broken and a contrite heart, O God, thou wilt not despise. A heart crushed is a fragrant heart. Men contemn those who are contemptible in their own eyes, but the Lord seeth not as man seeth. He despises what men esteem, and values that which they despise. Never yet has God spurned a lowly, weeping penitent, and never will he while God is love, and while Jesus is called the man who receiveth sinners. Bullocks and rams he desires not, but contrite hearts he seeks after; yea, but one of them is better to him than all the varied offerings of the old Jewish sanctuary.

How are you doing in this area? Is your worship perfunctory? hypocritical? devoid of obedience and a brokenness over your sin?

AND THERE REMEMBER THAT YOUR BROTHER HAS SOMETHING AGAINST YOU (Ge 41:9; 42:21,22; 50:15, 16, 17; Lv 6:2, 3, 4, 5, 6; 1Ki 2:44; Lam 3:20; Ezek 16:63; Lk 19:8)

Remember (3403) (mnaomai) means to recall information from memory. Why would one "remember"? Undoubtedly the convicting ministry of the Holy Spirit plays the key roll in prompting such a recall. And when you remember act on that truth. Don’t wait for your angry brother or sister to take the first step. You take it, and take it quickly before things get worse!

Mnaomai - 23x in 23v - Mt 5:23; 26:75; 27:63; Lk 1:54, 72; 16:25; 23:42; 24:6, 8; John 2:17, 22; 12:16; Acts 10:31; 11:16; 1 Cor 11:2; 2Ti 1:4; Heb 2:6; 8:12; 10:17; 13:3; 2Pe 3:2; Jude 1:17; Rev 16:19

Brother (80) (adelphos from a = denoting unity + delphus = womb) refers to one from the same womb, and in this case is used by Jesus more generally to refer to one of the same nature, for all men are born into Adam. So here Jesus refers to a fellow man as a brother

Jesus is calling for the offender to take the initiative in this process. That is, even if we hold nothing against him, if he is angry with or hates us, we should do everything in our power to be reconciled to him. We might have expected Jesus to focus primarily on the offended party, since they are the most likely to feel anger towards another. Instead, in these verses it is the offender who initiates the process of reconciliation. Elsewhere Jesus urges the offended party to make the first move (Mt 18:15). Both share an obligation to work for resolution when there has been a conflict. Ideally, the two would meet en route to one another and settle their differences “on the way.”

How important is it to deal with enmity, disagreements, animosity, or anger? Reconciliation is so important that it takes priority over everything else. It even takes precedence over worship. God would rather see us resolve our differences than receive our offerings!

Let's get practical for a moment. Do you know someone who is angry with you? Is there someone who has offended you? How can you take the initiative in each case to reconcile with that person? Before attempting to reconcile, take some time to think through your strategy. For example, reconciliation may be better attempted face to face rather than over the phone. You may even want to write out what you will say in advance. Note that there is no way to guarantee how the other person will respond, but you can be certain of God’s help as you “make every effort” to be at peace with all men.

Luke gives us an excellent example of a new citizen of the Kingdom of heaven who put this into practice...

And Zaccheus (a chief tax gatherer) stopped and said to the Lord, "Behold, Lord, half of my possessions I will give to the poor, and if I have defrauded anyone of anything, I will give back four times as much." And Jesus said to him, "Today salvation has come to this house, because he, too, is a son of Abraham. For the Son of Man has come to seek and to save that which was lost." (Luke 19:8-10)

The Preacher's Commentary has the following illustration of reconciliation (albeit it deals with anger in the one who remembers)...

At a communion service in the South Pacific Islands, a man kneeling at the altar to receive the emblems suddenly got up and moved to the back of the auditorium with an agitated expression. Later he rejoined the communicants and participated in the sacrament. When asked, following the service, about his action, he revealed that he had seen the man kneeling at the other end of the altar rail who had killed his father. He was so angry in his spirit that he could not partake of the emblems until God enabled him to experience a forgiving spirit. Just so, Jesus elevates reconciliation with one’s brother to a greater importance than religious rites. And the ministry of reconciliation was ultimately expressed by the Master who, while we were enemies, died for us. (Augsburger, M. S., & Ogilvie, L. J. Vol. 24: The Preacher's Commentary Series, Volume 24: Matthew. Nashville, Tennessee: Thomas Nelson Inc) (Ed note: see the serious warning regarding taking communion in an unworthy manner in 1Cor 11:27-34 )

Today in the Word has the following devotional on Jesus' teaching in Mt 5:23-24...

LEAVE YOUR OFFERING THERE BEFORE THE ALTAR AND GO: aphes (2SAAM) ekei to doron sou emprosthen tou thusiasteriou kai hupage (2SPAM) (Mt 18:15, 16, 17; Job 42:8; Proverbs 25:9; Mark 9:50; Romans 12:17,18; 1Corinthians 6:7,8; 1Timothy 2:8; James 3:13, 14, 15, 16, 17, 18; 5:16; 1Peter 3:7,8)

Spurgeon comments that...

It is said that, in Hindostan, there is a complete divorce of religion from morality, so that a man may be supposed to be eminently religious even while living in the utmost filthiness and vice; but it must never be so among us. We must never imagine that God can accept an offering from us while we harbor any enmity in our hearts. Perhaps, after reading this passage, you say, “If I had anything against my brother, I would go to him at once, and seek to be reconciled to him.” That would be quite right; but you must go further than that, for Christ says, “If thou bring thy gift to the altar, and there rememberest that thy brother hath ought against thee.” It is much more easy to go to the man who has wronged you than to the one whom you have wronged. Yet the second is evidently the clearer duty, and should be attended to at once: neither can we expect the Lord to attend to us unless we attend to this duty.

Leave (863) (aphiemi [word study] from apo = prefix implies separation + hiemi = put in motion, send) conveys the basic idea of an action which causes separation and means to send from one's self, to forsake, to hurl away, to put away, let alone, disregard, put off. It conveys the basic idea of an action which causes separation and refers to total detachment, total separation, from a previous location or condition. It means to send forth or away from one's self. It refers to the act of putting something away or of laying it aside. In secular Greek aphiemi initially conveyed the sense of to throw and in one secular writing we read "let the pot drop" (aphiemi). From this early literal use the word came to mean leave or let go.

This verb presents the interesting picture - "Let go of your offering".

Offering (1435) (doron) a gift offered to God (eg, to honor Him, Mt 2:11). A present. An offering (used to support gift to maintain divine service, Lk 21:4 ~ the "offering box") .

Doron - 19x in 17v - Matt 2:11; 5:23f; 8:4; 15:5; 23:18f; Mark 7:11; Luke 21:1, 4; Eph 2:8; Heb 5:1; 8:3f; 9:9; 11:4; Rev 11:10. The NAS renders doron as  gift(1), gifts(8), given(2), offering(8).

Before (1715) (emprosthen) in front of.

Emprosthen - 48x in 45v - Matt 5:16, 24; 6:1f; 7:6; 10:32f; 11:10, 26; 17:2; 18:14; 23:13; 25:32; 26:70; 27:11, 29; Mark 2:12; 9:2; Luke 5:19; 7:27; 10:21; 12:8; 14:2; 19:4, 27f; 21:36; John 1:15, 30; 3:28; 10:4; 12:37; Acts 10:4; 18:17; 2 Cor 5:10; Gal 2:14; Phil 3:13; 1 Thess 1:3; 2:19; 3:9, 13; 1 John 3:19; Rev 4:6; 19:10; 22:8. The NAS renders it as ahead(3), before(30), higher rank(2), in front(1), in front of(3), in the presence of(4), in the sight of(3).

Jesus' point is that anger and hatred affect our relationship to God. As long as there is internal sin, outward acts of worship are not acceptable to God. Reconciliation must precede worship because unresolved conflict has priority and must be settled. Settle the breach between you and your brother before you try to settle the breach between you and God. Not to do that is to be a hypocrite by asking for forgiveness without repenting.

Mark it down beloved. If you bring anger to the altar, you cannot worship God, so get rid of the anger quickly. Do not be deceived. Is there someone God's Spirit is bringing to your mind to reconcile with so that you might then worship Him in spirit and in truth? The Father desires and seeks true worshipers (John 4:23). Don't put off until tomorrow what you should deal with today. And remember your obligation is only as far as it is possible (the other party may make it totally impossible) for you to be at peace with all men (see Romans 12:14-17; 12:18-21). A clear, clean conscience  is a wonderful thing.

FIRST BE RECONCILED TO YOUR BROTHER AND THEN COME AND PRESENT YOUR OFFERING:  proton diallageqi (2SAPM) to adelphos sou, kai tote elthon (AAPMSN) prosphere (2SPAM) to doron sou (Mt 23:23; 1Co 11:28)

First (4413) (proton) means first in time, place, order or importance. Here Jesus speaks of the priority, and the necessity that reconciliation of an animosity should take over worship. 

Be reconciled (1259) (diallasso from diá = denoting transition + allasso [word study] = to change - see Reconciliation or Reconcile) means to change one's feelings towards another and so to become reconciled. It means to be restored to normal relations or harmony with someone. This could apply to a enmity, animosity or a quarrel in which the fault may be two-sided or one-sided. The context must show which side the active enmity is on, but in this case it is the brother who is somehow offended.

Jesus teaches that we should take every reasonable step to promote an effect opposite of murder (whether it is with or without guns or knives). In this case, instead of murdering by hand or mouth, citizens of the Kingdom of Heaven are those who should seek with all their power to establish right relationships with their brothers.

Brothers is used in the sense not of the Christian brotherhood but in the sense that all mankind is related through Adam's lineage ("the brotherhood of mankind") and all are to be treated as those made in the image of God.

Present (4374) (prosphero from pros = before + phero = bear) to bear before and so to bring unto.

John MacArthur wisely comments that

Obviously we cannot change another person’s heart or attitude, but our desire and effort should be to close the breach as much as is possible from our side and to hold no anger ourselves even if the other person does. Regardless of who is responsible for the break in relationship-and often there is guilt on both sides-we should determine to make a reconciliation before we come before God to worship. True worship is not enhanced by better music, better prayers, better architecture, or even better preaching. True worship is enhanced by better relationships between those who come to worship. Worship may be improved by our staying away from church until we have made things right with those with whom we know our relationship is strained or broken. When there is animosity or sin of any sort in our heart there cannot be integrity in our worship. (MacArthur, J: Matthew 1-7 Macarthur New Testament Commentary Chicago: Moody Press) (Bolding added)

Sinclair Ferguson draws an illustration...

Picture a man in church. He is about to express his devotion to the Lord in worship and in his offering. But he has not been enjoying fellowship with his brother. There is disharmony in the relationship. Jesus says the man should leave his offering, be reconciled to his brother, and then return to worship God with a clear conscience and full heart. Is Jesus saying that the only important thing in worship is right relationships with our fellow men? Hardly! He recognizes that our relationship with God is primary, but we always appear before God as those who are related, rightly or wrongly, to our fellow men. What we are before God involves how we are related to others (cf 1Jn 1:6, 7). And if we are at enmity with others, how can we come into the Lord's presence with clean hands and a pure heart (cf Mt 5:8-note)? It is monstrous to think that he will find our hypocritical offering acceptable. Obedience is better than sacrifice (1Sa 15:22). As Peter shows, this principle extends to the home and family: husbands are to treat their wives with respect and as heirs of the gracious gift of life so that nothing will hinder their prayers (1Pe 3:7-note). The principle is clear: right relationships with others are part of the meaning of the commandment not to murder. They are essential if our righteousness is to go down deeper than that of the scribes and Pharisees.  (Ferguson, Sinclair: Sermon on the Mount :Banner of Truth) (Bolding added)

Max Lucado quips...

As far as I know, this is the only time God tells you to slip out of church early. Apparently, he’d rather have you give your olive branch than your tithe. If you are worshiping and remember that your mom is hacked-off at you for forgetting her birthday, then get off the pew and find a phone. Maybe she’ll forgive you; maybe she won’t. But at least you can return to your pew with a clean conscience. (Lucado, M.  When God Whispers Your Name. Page 127. Dallas: Word Pub).

G Campbell Morgan writes that...

God seeks and values the gifts we bring Him—gifts of praise, thanksgiving, service, and material offerings. In all such giving at the altar we enter into the highest experiences of fellowship. But the gift is acceptable to God in the measure to which the one who offers it is in fellowship with Him in character and conduct; and the test of this is in our relationships with our fellow men. We are thus charged to postpone giving to God until right relationships are established with others. Could the neglect of this be the explanation of the barrenness of our worship?

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F B Meyer has the following devotional thoughts entitled "First, Reconciliation" focusing on Mt 5:23-24...

THERE IS a marked difference between memory and recollection.

Memory resembles a great box or chest into which a man casts his letters, accounts, and MSS.; recollection is the readiness, be it less or more, with which he can lay his hand on what he requires. We know that it is somewhere in our possession, we remember to have seen and turned it over, but search as we may we cannot find or recall it.

But there is a moment of quickened recollection when we stand before God: "When thou bringest thy gift to the altar and rememberest." As the Divine searchlight plays upon our past life it reveals many things which had passed from our mind. Conscience is a keen quickener of our powers of recollection.

What has your brother against you? This--that you flamed out against him in passion, with bitter, angry words, in hatred and contempt; or this--that you have been sullen and sulky, scarcely answering his advances, meeting his salutations with grudging courtesy. Perhaps you have done him a positive wrong, and have taken from him his only covering, or have forborne to help him when he stood in sore need (Ex 22:26, 27;  23:4, 5, 6, 7, 8, 9).

We are bidden to get right with man, as the first step to acceptance with God--" first be reconciled to thy brother." Humility is necessary in every approach to God, and nothing so humbles our pride as to confess our faults to our brethren. Truth is necessary to all right dealings with God, and nothing will so promote truth in our inward parts as to be transparent and simple in our dealings with our fellows. Sincerity in confession of sin is an essential beginning of peace with God, but how can we be sure that our confession is sincere unless it costs us something more than words. "'First, be reconciled with thy brother"--not only with the brother of human flesh--but with our great Brother in the Glory (Ge 1:17, 18, 19, 20, 21; He 2:11 [note]). Then comet Offer thyself, as thy gift; He will accept thee, and thy gifts.

PRAYER Give unto us, O Lord, we beseech Thee, broken and contrite hearts. Help us to do all that ought to be done to make amends, and grant unto our brother the willingness to meet us with forgiveness and peace. So shall we have peace with Thee, our Elder Brother, against whom we have grievously sinned. AMEN. (Our Daily Walk)

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Today in the Word has the following devotional thoughts on Mt 5:23, 24...

When D. L. Moody was four years old, his father died, leaving a large, impoverished family. The eldest son ran away from home, but each night his mother put a light in the window, hoping for his return. Mr. Moody recalled that when his older brother did come home, he was barely recognizable behind a heavy beard. It was only as he began to cry that Mrs. Moody realized it was her son and invited him in. ""No, mother,"" he said, ""I will not come in until I hear first that you have forgiven me."" Mrs. Moody threw her arms around her son and brought him indoors. Moody's older brother was clearly in the wrong and he knew it, which made his mother's gift of forgiveness and reconciliation a special one. We as believers have the gift of re-conciliation to offer others, and Jesus urges us to give it freely. In fact, Jesus commands us to initiate reconciliation whether we are in the right or in the wrong. In Matthew 5:23-24, Jesus doesn't define who is the guilty party or who is responsible for the broken relationship. The point is not to assign blame, but to make the situation right. The same is true in the courtroom scene Jesus outlined in verses 25-26. He didn't say the person being taken to court will definitely be found guilty, although that seems to be the likely outcome if the case goes to trial. It doesn't matter who's right or who's wrong--again, the point is to ""settle matters quickly.""

Taking the first step in re-conciliation is our responsibility as believers. When we fail to do so, we often try to justify ourselves by saying something like, ""I'm not mad at her, she's mad at me. It's her problem. She needs to deal with it."" But Jesus turns that kind of logic upside-down. God wants us to do everything we can to remove barriers and offenses between us and other Christians. Otherwise, our acts of worship are hollow to Him. That ought to be motivation enough to seek peace!  Let's admit it. These are tough commands to follow. Why? Because it's difficult for us to set aside the issue of blame. When we feel we are innocent, most of us want justice. It's only when we are in the wrong that we want mercy.

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Our Daily Bread has the following devotionals - These are used by permission of Radio Bible Class (Our Daily Bread, Copyright RBC Ministries, Grand Rapids, MI. Reprinted by permission. All rights reserved)

Going Straight- How far would you travel to put things right with a brother who hadn't spoken to you in 10 years? Would you go 300 miles from Iowa to Wisconsin? On a riding lawn mower?

Unable to drive a car and despising bus travel, Alvin Straight did exactly that in the intriguing film The Straight Story. It is the true-life drama of a 73-year-old man who decided it was time to end the silence, stop the hating, and break down the wall of anger he and his brother had built between them.

As I watched the film in a packed theater, where the audience was silent from beginning to end, I thought of all the broken relationships that must have surfaced in the minds of people sitting there in the darkness. I also pondered the words of Jesus about setting things right with those from whom we've been estranged. He said, "If you bring your gift to the altar, and there remember that your brother has something against you, leave your gift there before the altar, and go your way. First be reconciled to your brother, and then come and offer your gift" (Matthew 5:23, 24).

Is there a relative, a friend, or a brother in Christ with whom you need to make things right? Then why not go straight to that person and do it today? —D C McCasland

Lord, let me feel the pain of a wounded soul
And seek to heal that wounded one I pray;
Yes, I would take the reconciling role,
And bring an end to pain and strife today. —Hess

An offense against your neighbor builds a fence between you and God.

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$7.23 Plus Pride- As I was studying the Old Testament law about making restitution for theft and property loss, I began to wonder how it applied to me. Immediately the words Bill's pump came to mind. Months before, I had borrowed my neighbor's pump to inflate a bicycle tire. It broke while I was using it. But I'm ashamed to admit that I returned it without saying anything to him.

It was obvious that God wanted me to confess my wrong to Bill and buy him a new pump. But my rationalizations were swift: It was old, and it would have broken anyway. It would be embarrassing to reveal my failure and show what a weak Christian I am.

My excuses sounded hollow. I knew the Lord wanted me to make it right. So I bought a pump and went over to Bill's house, but he was out of town. At church the next morning, I started to drop my offering in the plate and remembered, "First be reconciled to your brother, and then come and offer your gift" (Mt. 5:24). The money went back in my pocket.

When Bill returned, I told him what I'd done, apologized, and gave him the new pump. He graciously understood. It cost $7.23 plus pride--a small price to restore a relationship with a neighbor and a clear conscience with God. --D C McCasland

Show us, Lord, where we have failed
And sinned against a brother;
Give us courage to confess
Our faults to one another. --Sper

The only way to make things right is to admit that you've been wrong.

Charles Simeon writes...

IT is thought by many, that prudential considerations are unworthy the attention of a Christian. That he ought to be influenced by higher principles, we readily admit. The love of Christ should be to him in the place of all other incentives, so far at least that he should not need any other motive for doing the will of God. But Christians are men, and feel the force of every principle which can operate upon the human mind: and therefore subordinate motives may fitly be proposed to them in aid of those which are more worthy of their regard. Our blessed Lord, having explained the sixth commandment, inculcates the duties contained in it, particularly that of seeking reconciliation with an offended brother: and this he does, first from the consideration of the offence which a want of a conciliatory spirit gives to God, and next from a consideration of the danger to which it exposes ourselves. In the former view we have treated of it in the foregoing verses; in the latter view we are to speak of it at this time. But the peculiarly emphatic manner in which our Lord speaks in the words before us, will naturally, and almost necessarily, lead our thoughts beyond the mere concerns of time, to another tribunal before which we must all appear. (Read the entire sermon - Matthew 5:25, 26 The Importance of Seeking Reconciliation with God - Page 123)

Literally this read "be well minded towards" where the verb "be" (1510) is a command in the present imperative, calling for it to be the continual attitude and action of citizens of the kingdom of heaven.

Spurgeon writes that...

There is nothing like ending disputes at once, before the rancor grows, and your adversary becomes determined to push you to extremes. Oh, for more of that spirit of yielding! You know how people say, “If you tread on a worm: it will turn;” but, brethren, a worm is not an example for a Christian, even if the poor wounded creature does turn toward you in its agony. If you turn, turn to kiss the hand that smites you, and to do good to them that evil entreat you.

Make friends (2132) (eunoeo from eúnoos = benevolent, kindly from eú = well + noús = mind) means be well–disposed, well-minded towards or well–intentioned toward another, to be friends (Mt 5:25) and inclined to satisfy by paying or compromising. Jesus is using an illustration from the common practice of imprisoning a person for an unpaid debt. He is teaching that if someone holds a debt of any sort against us, he is to make it good as soon as possible and before it is too late and he is imprisoned.

Quickly (5035) (tachu) pertains to a very short extent of time and so means this making of friends is to be carried out  hurriedly, speedily or with haste. Jesus is calling for reconciliation to be sought eagerly, aggressively and quickly even if it involves self-sacrifice. Paul alludes to the fact that it is better to be wronged than to allow a dispute between brethren to be a cause for dishonoring Christ

Actually, then, it is already a defeat for you, that you have lawsuits with one another. Why not rather be wronged? Why not rather be defrauded? (1Cor. 6:7).

Opponent (476) (antidikos from antí = against + díke = cause or suit at law)  refers to an opponent in a lawsuit. Antidikos is used once of the devil (see notes 1 Peter 5:8) the accuser of the brethren. Roman law provided that a plaintiff could bring the accused with him to face the judge. The two themselves could settle the matter on the way, but not after the court became involved.

Here the antidikos, the opponent or adversary is some kind of opponent to whom we apparently owe money and who is apparently in a position to take legal action, without further specific information as to his identity or the nature of the case.

On the way or on the road while not specific adds obviously emphasis to the urgency of the call to reconcile. In other words, don't wait until you get to the lobby of the courthouse! Once the legal process is set in motion, the judge will pass sentence and its too late to settle. Don't miss the golden opportunity to settle. It is interesting that the background here seems to be non-Jewish since the Jews did not imprison for debt.

Freeman in Manners and Customs of the Bible has the following summary of Mt 5:25:...

According to Roman law, if a person had a quarrel that he could not settle privately, he had the right to order his adversary to accompany him to the praetor (Roman magistrate ranking below a consul and having chiefly judicial functions). If he refused, the prosecutor took someone present to witness by saying, “May I take you to witness?” If the person consented, he offered the tip of his ear, which the prosecutor touched; a form that was observed toward witnesses in some other legal ceremonies among the Romans. Then the plaintiff (one bringing the legal action) might drag the defendant to court by force in any way, even by the neck, but worthless persons such as thieves and robbers might be dragged before the judge without the formality of calling a witness. If on the way to the judge the difficulty was settled, no further legal steps were taken. Jesus refers to this custom in the text. When the accused is thus legally seized by the accuser, he is urged to make up his quarrel while on the way to the judge, so that no further legal process should be necessary. (Freeman, J. M., & Chadwick, H. J. Manners & Customs of the Bible. 1996. Whitaker House)

SO THAT YOUR OPPONENT MAY NOT HAND YOU OVER TO THE JUDGE AND THE JUDGE TO THE OFFICER, AND YOU BE THROWN INTO PRISON: mepote se parado (3SAAS) o antidikos to krite, kai o krites to huperete, kai eis phulaken blethese; (2SFPI) (Job 22:21; Psalms 32:6; Isaiah 55:6,7; Luke 13:24,25; 2Cor 6:2; Hebrews 3:7,13; Hebrews 12:17) (1Ki 22:26,27)

Opponent (476) (antidikos [word study] from anti = against + dike = a cause or suit at law) was used first as a word for an opponent in a lawsuit and then came to mean an adversary or enemy without reference to legal affairs. It describes one who is actively and continuously hostile toward someone. An adversary is one that contends with, opposes, or resists.

Antidikos - 5x in 4v - Matt 5:25; Luke 12:58; 18:3; 1 Pet 5:8. NAS renders it as  adversary(1), opponent(3), opponent at law(1).

Hand over (3860)( paradidomi [word study] from para = alongside, beside,  to the side of, over to + didomi = to give) conveys the  basic meaning of to give over from one's hand to someone or something, especially to give over to the power of another. Synonyms used for paradidomi include surrender, yield up, entrust, deliver up, give over.

Paradidomi -119x in 117v - Matt 4:12; 5:25; 10:4, 17, 19, 21; 11:27; 17:22; 18:34; 20:18f; 24:9f; 25:14, 20, 22; 26:2, 15f, 21, 23ff, 45f, 48; 27:2ff, 18, 26; Mark 1:14; 3:19; 4:29; 7:13; 9:31; 10:33; 13:9, 11f; 14:10f, 18, 21, 41f, 44; 15:1, 10, 15; Luke 1:2; 4:6; 9:44; 10:22; 12:58; 18:32; 20:20; 21:12, 16; 22:4, 6, 21f, 48; 23:25; 24:7, 20; John 6:64, 71; 12:4; 13:2, 11, 21; 18:2, 5, 30, 35f; 19:11, 16, 30; 21:20; Acts 3:13; 6:14; 7:42; 8:3; 12:4; 14:26; 15:26, 40; 16:4; 21:11; 22:4; 27:1; 28:17; Rom 1:24, 26, 28; 4:25; 6:17; 8:32; 1 Cor 5:5; 11:2, 23; 13:3; 15:3, 24; 2 Cor 4:11; Gal 2:20; Eph 4:19; 5:2, 25; 1 Tim 1:20; 1 Pet 2:23; 2 Pet 2:4, 21; Jude 1:3. The NAS renders paradidomi as betray(13), betrayed(9), betraying(9), betrays(3), commended(1), committed(3),deliver(10), deliver up(7), delivered(17), delivered over(2), delivered up(16), delivering(3), delivers up(1), entrusted(3),entrusting(1), gave over(3), gave up(3), given over(1), handed down(3), handed over(4), permits(1), put(1), putting(1),risked(m)(1), taken custody(2), turn over(1).

Judge (2923) (krites) is one who has the right to render a decision in legal matters, one who passes judgment on anything or who makes decisions based on examination and evaluation (refers to both human and divine judges - God in Acts 10:42).

Krites - 19x in 17v  - Matt 5:25; 12:27; Luke 11:19; 12:14, 58; 18:2, 6; Acts 10:42; 13:20; 18:15; 24:10; 2 Tim 4:8; Heb 12:23; Jas 2:4; 4:11f; 5:9

Officer (5257) (huperetes from hupó = under, beneath + erétes = a rower or eresso = to row) is literally an under rower or an under-oarsman on the ship with several ranks of rowers. These were the men down in the ship's, doing one thing -- rowing and with their eyes on one man, the man standing at the front of the hull, shouting "Row, Row, Row."! 

Huperetes - 20x in 20v - Matt 5:25; 26:58; Mark 14:54, 65; Luke 1:2; 4:20; John 7:32, 45f; 18:3, 12, 18, 22, 36; 19:6; Acts 5:22, 26; 13:5; 26:16; 1 Cor 4:1. The NAS renders huperetes as attendant(1), helper(1), minister(1), officer(1), officers(13), servants(3).

Huperetes described the bottom rower, the galley-slave, then any servant, the attendant in the synagogue (Luke 4:20). Luke describes John Mark in his relation to Barnabas and Saul (Acts 13:5) as a huperetes. Luke also applies huperetes to the “ministers of the word” (Luke 1:2).  The idea is that of a subordinate, a servant, an attendant, or an assistant in general. Here Jesus refers to the subordinate official who waited to accomplish the commands of his superior.

Prison (5438) (phulake from phulasso = watch, keep from escaping, be on guard) describes the place where someone is watched, guarded or kept in custody and thus a prison. In context Jesus is referring to debtor’s prison, (as implied by the phrase "until you have paid up the last cent") where the person could work to earn back what he had defrauded.

Phulake - 47x in 45v - Matt 5:25; 14:3, 10, 25; 18:30; 24:43; 25:36, 39, 43f; Mark 6:17, 27, 48; Luke 2:8; 3:20; 12:38, 58; 21:12; 22:33; 23:19, 25; John 3:24; Acts 5:19, 22, 25; 8:3; 12:4ff, 10, 17; 16:23f, 27, 37, 40; 22:4; 26:10; 2 Cor 6:5; 11:23; Heb 11:36; 1 Pet 3:19; Rev 2:10; 18:2; 20:7. The NAS renders phulake as  guard(1), imprisonment(1), imprisonments(2), prison(34), prisons(3), time of the night(1),watch(4).

Jesus is using this illustration from secular life as a picture of sin against another person. He is emphasizing that such sin, like unpaid debts, must be resolved quickly to avoid having to face a sentence from the divine Judge.  We are to make every effort, with no delay, to make our relationship right with our brother (not speaking of Christian brothers but of mankind in general) before our relationship can be right with God and we can avoid chastening.

MacDonald notes that...

While there is some disagreement among scholars about the identity of the people in this parable, the point is clear: if you are wrong, be quick to admit it and make things right. If you remain unrepentant, your sin will eventually catch up with you and you will not only have to make full restitution but suffer additional penalties as well. And don’t be in a hurry to go to court. If you do, the law will find you out, and you will pay the last penny.  (MacDonald, W., & Farstad, A. Believer's Bible Commentary : Old and New Testaments. Nashville: Thomas Nelson)

Hagner sums up Mt 26-27 noting that...

In His exegesis of the truest meaning of the Mosaic commandment—and presentation of the level of righteousness required by the kingdom—Jesus goes far beyond the letter of the text (where some may have been inclined to stop). By his explication of “thou shalt not murder,” Jesus penetrates to the spirit of the commandment. Since the spring of a person’s conduct is the heart, or inner person, the transforming power of the kingdom must be especially experienced there. Anger and insults spoken from anger are evil and corrupting, and they therefore call forth God’s judgment, just as the act of murder itself does. Accordingly, the worship and service of God cannot be performed as long as anger infects the soul. Thus, the recipient of the grace of the kingdom is one who initiates and seeks reconciliation, both with members of the community of faith and with adversaries (cf. Mt 5:9). The underlying and key message of these astonishingly authoritative words is that a person is held accountable for his or her angry thoughts, not merely for external acts of violence against others. Here, as in the beatitudes, the truly revolutionary character of the kingdom and its ethics makes itself felt. (Hagner, D. A. Vol. 33A: Word Biblical Commentary: Matthew 1-13. Word Biblical Commentary Page 118. Dallas: Word, Incorporated)

Virgil Hurley has the following illustration entitled "Even in Wartime"

On April 1, 1945, in the Taiwan Strait, the U.S. submarine Queenfish fired multiple torpedoes at what the ship’s radar suggested was a Japanese destroyer. When the sub later pulled aboard the only survivor, the captain learned he had sunk the Awa Maru, a Japanese cargo ship the U.S. State Department had guaranteed safe passage for a round-trip from Japan to Singapore. With white crosses painted on her hull and two thousand tons of relief supplies for American soldiers in Japanese prison camps in her hold, the Awa Maru was to pass unharmed through the gauntlet of submarines swarming the depths in her path. The Queenfish never received a clear version of that order.

On April 17, the U.S. State Department and the U.S. Navy issued an official apology to the Japanese government, offering to replace the Awa Maru with a similar ship. It didn’t have to be done because the war ended four months later.

as if Jesus were saying, “Be not surprised about the urgency of my command that you be reconciled; for, should it be that you were to pass from this life with a heart still at variance with your brother, a condition which you have not even tried to change, that wrong would testify against you in the day of judgment. Moreover, dying with that spirit of hatred still in your heart, you will never escape from the prison of hell.” (Hendriksen, W., & Kistemaker, S. J. Vol. 9: New Testament commentary : Exposition of the Gospel According to Matthew. Page 301. Grand Rapids: Baker Book House)

Let me add to Hendriksen's comment that the emphasis I would place is on his statement "a condition which you have not even tried to change". Jesus is not saying we can earn our salvation or lose our salvation. What He is saying is that if you are genuinely saved, you are in a New Covenant (Jeremiah 31:31, 32, 33, 34), possess a new heart and a new Spirit (Ezekiel 36:26, 27), and so you have the motivation (the Law is now written in your heart and the Spirit will cause you to walk in God's statutes) to seek reconciliation. The person who never has any desire whatsoever to seek reconciliation is not manifesting a new heart which seeks to deal with hatred. Now, you may be asking "How far do I go? Is the burden on me entirely? What happens when the one in adversarial relation refuses?" The answer is when you have done all in your power to seek to bring about a reconciliation, and the one at enmity refuses, the guilt will rest on the adversary. Jesus Himself sought reconciliation with evil men who repeatedly refused and who themselves will pay the penalty.