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Translation
King James Version
Agree with thine adversary quickly, whiles thou art in the way with him; lest at any time the adversary deliver thee to the judge, and the judge deliver thee to the officer, and thou be cast into prison.
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KJV (with Strong's)
Agree G2468 G2132 with thine G4675 adversary G476 quickly G5035, whiles G2193 G3755 thou art G1488 in G1722 the way G3598 with G3326 him G846; lest at any time G3379 the adversary G476 deliver G3860 thee G4571 to the judge G2923, and G2532 the judge G2923 deliver G3860 thee G4571 to the officer G5257, and G2532 thou be cast G906 into G1519 prison G5438.
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Complete Jewish Bible
If someone sues you, come to terms with him quickly, while you and he are on the way to court; or he may hand you over to the judge, and the judge to the officer of the court, and you may be thrown in jail!
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Berean Standard Bible
Reconcile quickly with your adversary, while you are still on the way to court. Otherwise, he may hand you over to the judge, and the judge may hand you over to the officer, and you may be thrown into prison.
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American Standard Version
Agree with thine adversary quickly, while thou art with him in the way; lest haply the adversary deliver thee to the judge, and the judge deliver thee to the officer, and thou be cast into prison.
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World English Bible Messianic
Agree with your adversary quickly, while you are with him on the way; lest perhaps the prosecutor deliver you to the judge, and the judge deliver you to the officer, and you be cast into prison.
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Geneva Bible (1599)
Agree with thine aduersarie quickly, whiles thou art in the way with him, lest thine aduersarie deliuer thee to the Iudge, and the Iudge deliuer thee to ye sergeant, and thou be cast into prison.
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Young's Literal Translation
`Be agreeing with thy opponent quickly, while thou art in the way with him, that the opponent may not deliver thee to the judge, and the judge may deliver thee to the officer, and to prison thou mayest be cast,
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In the KJVVerse 23,260 of 31,102

Study This Verse

SUMMARY

Matthew 5:25, delivered by Jesus within the profound teachings of the Sermon on the Mount, serves as a pragmatic and urgent exhortation to seek swift reconciliation with an opponent, particularly in the context of a legal or relational dispute. It underscores the wisdom of proactive peacemaking to prevent the escalation of conflict, which can lead to increasingly severe consequences, culminating in imprisonment or a state of dire restriction. This verse extends Jesus's broader call for internal righteousness and relational harmony, emphasizing the critical importance of addressing grievances before they spiral out of control.

CONTEXT

  • Literary Context: This verse is situated within Jesus's exposition on true righteousness, following His reinterpretation of the Mosaic Law in the Sermon on the Mount. Specifically, it immediately follows His teaching on anger and reconciliation in Matthew 5:21-24, where He equates unjustified anger with murder and emphasizes the priority of reconciling with a brother before offering a gift at the altar. Matthew 5:25 then extends this principle from interpersonal anger to the practical, potentially legal, implications of unresolved conflict, urging swift action to avoid judicial consequences. It highlights that the righteousness of the Kingdom of God involves not merely refraining from outward sin but actively pursuing peace and justice in relationships.
  • Historical & Cultural Context: First-century Judea operated under a legal system that, while influenced by Roman authority, still retained elements of Jewish law and custom. Disputes could be brought before local magistrates or elders. The process, once initiated, could be slow, costly, and punitive, especially for the debtor or offender. Imprisonment often served not as a primary punishment but as a holding place until a debt was paid or a judgment rendered, with the "officer" (Greek: hypērétēs) being a court attendant or bailiff responsible for enforcing the judge's decree. Jesus's illustration would have resonated deeply with His audience, who understood the harsh realities of legal proceedings and the potential for debtors' prisons, where one might remain until the last penny was paid, as alluded to in Matthew 5:26.
  • Key Themes: Matthew 5:25 contributes significantly to several key themes within the Sermon on the Mount and the broader Gospel of Matthew. It reinforces the urgency of reconciliation, stressing that prompt action is essential to prevent minor disagreements from escalating into major catastrophes. It highlights the theme of prudence and wisdom, advising a pragmatic approach to conflict resolution that prioritizes amicable settlement over contentious litigation, thereby avoiding harsher judgments. Furthermore, it underscores the consequences of delay and unrighteousness, illustrating a clear progression of negative outcomes—from initial dispute to judicial judgment, enforcement, and ultimately, imprisonment—for those who fail to resolve conflict. This aligns with Jesus's consistent call for a righteousness that surpasses that of the scribes and Pharisees, emphasizing internal transformation and proactive peacemaking, as seen in passages like Matthew 5:9 and Matthew 7:1-5.

EXPOSITION AND ANALYSIS

Key Word Analysis

  • Agree (Greek, eunoéō, G2132): This word (G2132) means "to be well-minded" or "to be favorably disposed," implying a willing and amicable settlement rather than a forced concession. It suggests cultivating a spirit of goodwill and seeking a resolution rooted in mutual understanding and concession, not merely avoiding punishment. The KJV's "agree" captures the essence of reaching a favorable accord.
  • adversary (Greek, antídikos, G476): The term (G476) specifically refers to a legal opponent or plaintiff in a lawsuit. While the application extends beyond the courtroom, its primary meaning grounds Jesus's illustration in a concrete judicial context, emphasizing the seriousness of the dispute and the potential for formal legal action. It highlights the one who has a claim against you.
  • way (Greek, hodós, G3598): This word (G3598) literally means a "road" or "journey," but figuratively refers to a "mode or means" or "progress." In this context, "in the way with him" signifies being on the journey towards the legal authority, indicating a window of opportunity for resolution before the formal proceedings begin and the situation becomes irreversible. It implies a shared path or process that has not yet reached its final, binding destination.

Verse Breakdown

  • "Agree with thine adversary quickly,": This opening imperative sets the tone for the entire verse, emphasizing immediate and proactive reconciliation. The "adversary" is someone with a legitimate claim or grievance against you, and the urgency ("quickly") suggests that delay will only exacerbate the problem.
  • "whiles thou art in the way with him;": This clause defines the window of opportunity. "In the way" refers to the journey or process leading to judgment, implying that there is still a chance to resolve the dispute privately and amicably before it reaches the official legal system, where one loses control over the outcome.
  • "lest at any time the adversary deliver thee to the judge,": This introduces the first negative consequence of failing to agree. The "adversary" (plaintiff) formally hands over the case to the "judge," initiating legal proceedings and surrendering control of the dispute to an external authority.
  • "and the judge deliver thee to the officer,": The escalation continues. Once the judge has rendered a verdict, the "officer" (bailiff or court attendant) is tasked with enforcing the judgment, often by taking the condemned into custody. This signifies the loss of freedom and the imposition of external force.
  • "and thou be cast into prison.": This is the ultimate, most severe consequence in the illustration. Imprisonment, often for debt, meant a complete loss of liberty and the inability to resolve the situation until the full penalty was paid, highlighting the dire and restrictive outcome of unresolved conflict.

Literary Devices

Jesus employs several potent literary devices in Matthew 5:25 to convey His message with clarity and impact. The most prominent is Progression, specifically a Climax of escalating negative consequences. The sequence from "adversary" to "judge," then "officer," and finally "prison" vividly illustrates the dire trajectory of unresolved conflict. This step-by-step deterioration serves as a powerful warning, emphasizing that inaction leads to increasingly severe and restrictive outcomes. Furthermore, the entire scenario functions as a Metaphor or Analogy. While presented as a literal legal dispute, Jesus uses this common experience to illustrate a broader spiritual principle about the urgency of reconciliation in all areas of life, including one's relationship with God. The legal framework provides a tangible, relatable example for an abstract theological truth. The phrase "quickly" also introduces an element of Urgency, underscoring the critical importance of immediate action to avert disaster.

THEOLOGICAL AND THEMATIC CONNECTIONS

Matthew 5:25 offers profound theological and thematic connections, extending beyond mere legal advice to encompass principles of divine justice, human responsibility, and the nature of the Kingdom of God. It underscores the importance of proactive peacemaking as an expression of true righteousness, demonstrating that God values reconciliation and prompt resolution over protracted conflict. The passage implicitly connects to the concept of God's justice, suggesting that just as human judges enforce consequences for unresolved disputes, so too does God require accountability for our actions and relationships. The urgency to "agree quickly" reflects a divine wisdom that seeks to avert greater suffering and calls believers to embody the spirit of reconciliation that is central to the Gospel message.

REFLECTION AND APPLICATION

Matthew 5:25 challenges believers to adopt a proactive and humble posture toward conflict resolution in all areas of life. It calls us to recognize that unresolved disputes, whether personal, relational, or even spiritual, carry escalating consequences. The wisdom imparted is not merely about avoiding legal trouble, but about cultivating a heart that prioritizes peace, reconciliation, and justice. This means being willing to concede, to apologize, to forgive, and to seek common ground, even when we feel we are in the right. It compels us to examine our own contributions to conflict and to take the initiative to mend broken relationships before they fester and lead to greater pain, division, or spiritual stagnation. The pursuit of peace is not a sign of weakness, but of profound spiritual strength and maturity, reflecting the very character of Christ.

Questions for Reflection

  • What unresolved conflicts or tensions exist in your life right now (e.g., family, friends, colleagues, church)?
  • What steps can you take "quickly" to initiate reconciliation or resolution in one of these situations?
  • How might delaying resolution in these areas lead to greater "imprisonment" or negative consequences in your life or relationships?
  • In what ways does your pride or desire to "be right" hinder your ability to "agree with your adversary quickly"?

FAQ

What kind of "adversary" is Jesus referring to in this verse?

Answer: While the immediate context and the Greek word antídikos (G476) specifically refer to a legal opponent or plaintiff in a lawsuit, Jesus's teaching extends beyond the courtroom. The "adversary" can represent anyone with whom you have a significant unresolved conflict or grievance – a neighbor, a family member, a business associate, or even a fellow believer. The core principle is about addressing any relationship where there is contention and a potential for escalation, whether it leads to formal legal proceedings or simply to deeply broken relationships and personal distress.

Is this passage only about avoiding lawsuits, or does it have a broader spiritual meaning?

Answer: While the illustration uses a legal scenario, the principles are profoundly spiritual and broadly applicable. Jesus is teaching about the urgent need for reconciliation, peacemaking, and the avoidance of escalating conflict in all aspects of life. The "prison" can be understood metaphorically as any state of bondage, regret, or severe consequence—whether emotional, relational, or spiritual—that results from unaddressed sin or unresolved disputes. It's a call to proactive righteousness, extending the themes of Matthew 5:21-24 to practical engagement with those who have a claim against us.

What does "whiles thou art in the way with him" mean in a practical sense?

Answer: "Whiles thou art in the way with him" (Greek: hodós, G3598) signifies the window of opportunity that exists before a dispute reaches its point of no return. Practically, it means resolving the issue while it is still a personal matter, before it becomes public, formalized, or involves external authorities. It's the time when both parties are still "on the road" together, perhaps physically heading to court, but more broadly, still in a position to negotiate and settle amicably. Once the case is "delivered to the judge," control is lost, and the consequences become far more severe and difficult to reverse, leading to the "officer" and "prison."

CHRIST-CENTERED FULFILLMENT

Matthew 5:25, while offering practical wisdom for human relationships, finds its ultimate and profound fulfillment in the person and work of Jesus Christ. He is the one who enables us to "agree with our adversary" in the most significant sense: our reconciliation with God. Humanity, by its sin, stands as an "adversary" to a holy God, facing the ultimate "Judge" and the eternal "prison" of separation from Him. However, while we were "in the way" – living our lives, yet condemned by sin – God sent His Son. Jesus, through His atoning sacrifice on the cross, became the means by which we can "agree" with God, making peace through His shed blood (Colossians 1:20). He took upon Himself the judgment we deserved, so that we might avoid the eternal consequences. Furthermore, Jesus Himself is "the way" (John 14:6)—the only path to true reconciliation with God. By trusting in Him, we are delivered from the condemnation of the Judge and the eternal "prison" of hell, receiving instead forgiveness, righteousness, and eternal life. This ultimate act of reconciliation by Christ empowers believers to live out the principles of Matthew 5:25 in their daily lives, seeking peace and reconciliation with others, knowing that they themselves have been reconciled to God through the Lamb who takes away the sin of the world (John 1:29).

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Commentary on Matthew 5 verses 21–26

I. II. Main points1. 2. Sub-points(1.) (2.) Details

Christ having laid down these principles, that Moses and the prophets were still to be their rulers, but that the scribes and Pharisees were to be no longer their rulers, proceeds to expound the law in some particular instances, and to vindicate it from the corrupt glosses which those expositors had put upon it. He adds not any thing new, only limits and restrains some permissions which had been abused: and as to the precepts, shows the breadth, strictness, and spiritual nature of them, adding such explanatory statutes as made them more clear, and tended much toward the perfecting of our obedience to them. In these verses, he explains the law of the sixth commandment, according to the true intent and full extent of it.

I. Here is the command itself laid down (Mat 5:12); We have heard it, and remember it; he speaks to them who know the law, who had Moses read to them in their synagogues every sabbath-day; you have heard that it was said by them, or rather as it is in the margin, to them of old time, to your forefathers the Jews, Thou shalt not kill. Note, The laws of God are not novel, upstart laws, but were delivered to them of old time; they are ancient laws, but of that nature as never to be antiquated nor grow obsolete. The moral law agrees with the law of nature, and the eternal rules and reasons of good and evil, that is, the rectitude of the eternal Mind. Killing is here forbidden, killing ourselves, killing any other, directly or indirectly, or being any way accessory to it. The law of God, the God of life, is a hedge of protection about our lives. It was one of the precepts of Noah, Gen 9:5, Gen 9:6.

II. The exposition of this command which the Jewish teachers contended themselves with; their comment upon it was, Whosoever shall kill, shall be in danger of the judgment. This was all they had to say upon it, that wilful murderers were liable to the sword of justice, and casual ones to the judgment of the city of refuge. The courts of judgment sat in the gate of their principal cities; the judges, ordinarily, were in number twenty-three; these tried, condemned, and executed murderers; so that whoever killed, was in danger of their judgment. Now this gloss of theirs upon this commandment was faulty, for it intimated, 1. That the law of the sixth commandment was only external, and forbade no more than the act of murder, and laid to restraint upon the inward lusts, from which wars and fightings come. This was indeed the prōton pseudos - the fundamental error of the Jewish teachers, that the divine law prohibited only the sinful act, not the sinful thought; they were disposed haerere in cortice - to rest in the letter of the law, and they never enquired into the spiritual meaning of it. Paul, while a Pharisee, did not, till, by the key of the tenth commandment, divine grace let him into the knowledge of the spiritual nature of all the rest, Rom 7:7, Rom 7:14. 2. Another mistake of theirs was, that this law was merely political and municipal, given for them, and intended as a directory for their courts, and no more; as if they only were the people, and the wisdom of the law must die with them.

III. The exposition which Christ gave of this commandment; and we are sure that according to his exposition of it we must be judged hereafter, and therefore ought to be ruled now. The commandment is exceeding broad, and not to be limited by the will of the flesh, or the will of men.

1.Christ tells them that rash anger is heart-murder (Mat 5:22); Whosoever is angry with his brother without a cause, breaks the sixth commandment. By our brother here, we are to understand any person, though ever so much our inferior, as a child, a servant, for we are all made of one blood. Anger is a natural passion; there are cases in which it is lawful and laudable; but it is then sinful, when we are angry without cause. The word is eikē, which signifies, sine caus, sine effectu, et sine modo - without cause, without any good effect, without moderation; so that the anger is then sinful, (1.) When it is without any just provocation given; either for no cause, or no good cause, or no great and proportionable cause; when we are angry at children or servants for that which could not be helped, which was only a piece of forgetfulness or mistake, that we ourselves might easily have been guilty of, and for which we should not have been angry at ourselves; when we are angry upon groundless surmises, or for trivial affronts not worth speaking of. (2.) When it is without any good end aimed at, merely to show our authority, to gratify a brutish passion, to let people know our resentments, and excite ourselves to revenge, then it is in vain, it is to do hurt; whereas if we are at any time angry, it should be to awaken the offender to repentance, and prevent his doing so again; to clear ourselves (Co2 7:11), and to give warning to others. (3.) When it exceeds due bounds; when we are hardy and headstrong in our anger, violent and vehement, outrageous and mischievous, and when we seek the hurt of those we are displeased at. This is a breach of the sixth commandment, for he that is thus angry, would kill if he could and durst; he has taken the first step toward it; Cain's killing his brother began in anger; he is a murderer in the account of God, who knows his heart, whence murder proceeds, Mat 15:19.

2.He tells them, that given opprobrious language to our brother is tongue-murder, calling him, Raca, and, Thou fool. When this is done with mildness and for a good end, to convince others of their vanity and folly, it is not sinful. Thus James says, O vain man; and Paul, Thou fool; and Christ himself, O fools, and slow of heart. But when it proceeds from anger and malice within, it is the smoke of that fire which is kindled from hell, and falls under the same character. (1.) Raca is a scornful word, and comes from pride, "Thou empty fellow;" it is the language of that which Solomon calls proud wrath (Pro 21:24), which tramples upon our brother - disdains to set him even with the dogs of our flock. This people who knoweth not the law, is cursed, is such language, Joh 7:49. (2.) Thou fool, is a spiteful word, and comes from hatred; looking upon him, not only as mean and not to be honoured, but as vile and not to be loved; "Thou wicked man, thou reprobate." The former speaks a man without sense, this (in scripture language) speaks a man without grace; the more the reproach touches his spiritual condition, the worse it is; the former is a haughty taunting of our brother, this is a malicious censuring and condemning of him, as abandoned of God. Now this is a breach of the sixth commandment; malicious slanders and censures are poison under the tongue, that kills secretly and slowly; bitter words are as arrows that would suddenly (Psa 64:3), or as a sword in the bones. The good name of our neighbour, which is better than life, is thereby stabbed and murdered; and it is an evidence of such an ill-will to our neighbour as would strike at his life, if it were in our power.

3.He tells them, that how light soever they made of these sins, they would certainly be reckoned for; he that is angry with is brother shall be in danger of the judgment and anger of God; he that calls him Raca, shall be in danger of the council, of being punished by the Sanhedrim for reviling an Israelite; but whosoever saith, Thou fool, thou profane person, thou child of hell, shall be in danger of hell-fire, to which he condemns his brother; so the learned Dr. Whitby. Some think, in allusion to the penalties used in the several courts of judgment among the Jews, Christ shows that the sin of rash anger exposes men to lower or higher punishments, according to the degrees of its proceeding. The Jews had three capital punishments, each worse than the other; beheading, which was inflicted by the judgment; stoning, by the council or chief Sanhedrim; and burning in the valley of the son of Hinnom, which was used only in extraordinary cases: it signifies, therefore, that rash anger and reproachful language are damning sins; but some are more sinful than others, and accordingly there is a greater damnation, and a sorer punishment reserved for them: Christ would thus show which sin was most sinful, by showing which it was the punishment whereof was most dreadful.

IV. From all this it is here inferred, that we ought carefully to preserve Christian love and peace with our brethren, and that if at any time a breach happens, we should labour for a reconciliation, by confessing our fault, humbling ourselves to our brother, begging his pardon, and making restitution, or offering satisfaction for wrong done in word or deed, according as the nature of the thing is; and that we should do this quickly for two reasons:

1.Because, till this be done, we are utterly unfit for communion with God in holy ordinances, Mat 5:23, Mat 5:24. The case supposed is, "That thy brother have somewhat against thee," that thou has injured and offended him, either really or in his apprehension; if thou are the party offended, there needs not this delay; if thou have aught against thy brother, make short work of it; no more is to be done but to forgive him (Mar 11:25), and forgive the injury; but if the quarrel began on thy side, and the fault was either at first or afterwards thine, so that thy brother has a controversy with thee, go and be reconciled to him before thou offer thy gift at the altar, before thou approach solemnly to God in the gospel-services of prayer and praise, hearing the word or the sacraments. Note, (1.) When we are addressing ourselves to any religious exercises, it is good for us to take that occasion of serious reflection and self-examination: there are many things to be remembered, when we bring our gift to the altar, and this among the rest, whether our brother hath aught against us; then, if ever, we are disposed to be serious, and therefore should then call ourselves to an account. (2.) Religious exercises are not acceptable to God, if they are performed when we are in wrath; envy, malice, and uncharitableness, are sins so displeasing to God, that nothing pleases him which comes from a heart wherein they are predominant, Ti1 2:8. Prayers made in wrath are written in gall, Isa 1:15; Isa 58:4. (3.) Love or charity is so much better than all burnt-offerings and sacrifice, that God will have reconciliation made with an offended brother before the gift be offered; he is content to stay for the gift, rather than have it offered while we are under guilt and engaged in a quarrel. (4.) Though we are unfitted for communion with God, by a continual quarrel with a brother, yet that can be no excuse for the omission or neglect of our duty: "Leave there thy gift before the altar, lest otherwise, when thou has gone away, thou be tempted not to come again." Many give this as a reason why they do not come to church or to the communion, because they are at variance with some neighbour; and whose fault is that? One sin will never excuse another, but will rather double the guilt. Want of charity cannot justify the want of piety. The difficulty is easily got over; those who have wronged us, we must forgive; and those whom we have wronged, we must make satisfaction to, or at least make a tender of it, and desire a renewal of the friendship, so that if reconciliation be not made, it may not be our fault; and then come, come and welcome, come and offer thy gift, and it shall be accepted. Therefore we must not let the sun go down upon our wrath any day, because we must go to prayer before we go to sleep; much less let the sun rise upon our wrath on a sabbath-day, because it is a day of prayer.

2.Because, till this be done, we lie exposed to much danger, Mat 5:25, Mat 5:26. It is at our peril if we do not labour after an agreement, and that quickly, upon two accounts:

(1.)Upon a temporal account. If the offence we have done to our brother, in his body, goods, or reputation, be such as will bear action, in which he may recover considerable damages, it is our wisdom, and it is our duty to our family, to prevent that by a humble submission and a just and peaceable satisfaction; lest otherwise he recover it by law, and put us to the extremity of a prison. In such a case it is better to compound and make the best terms we can, than to stand it out; for it is in vain to contend with the law, and there is danger of our being crushed by it. Many ruin their estates by an obstinate persisting in the offences they have given, which would soon have been pacified by a little yielding at first. Solomon's advice in case of suretyship is, Go, humble thyself, and so secure and deliver thyself, Pro 6:1-5. It is good to agree, for the law is costly. Though we must be merciful to those we have advantage against, yet we must be just to those that have advantage against us, as far as we are able. "Agree, and compound with thine adversary quickly, lest he be exasperated by thy stubbornness, and provoked to insist upon the utmost demand, and will not make thee the abatement which at first he would have made." A prison is an uncomfortable place to those who are brought to it by their own pride and prodigality, their own wilfulness and folly.

(2.)Upon a spiritual account. "Go, and be reconciled to thy brother, be just to him, be friendly with him, because while the quarrel continues, as thou art unfit to bring thy gift to the altar, unfit to come to the table of the Lord, so thou art unfit to die: if thou persist in this sin, there is danger lest thou be suddenly snatched away by the wrath of God, whose judgment thou canst not escape nor except against; and if that iniquity be laid to thy charge, thou art undone for ever." Hell is a prison for all that live and die in malice and uncharitableness, for all that are contentious (Rom 2:8), and out of that prison there is no rescue, no redemption, no escape, to eternity.

This is very applicable to the great business of our reconciliation to God through Christ; Agree with him quickly, whilst thou art in the way. Note, [1.] The great God is an Adversary to all sinners, antidikos - a law-adversary; he has a controversy with them, an action against them. [2.] It is our concern to agree with him, to acquaint ourselves with him, that we may be at peace, Job 22:21; Co2 5:20. [3.] It is our wisdom to do this quickly, while we are in the way. While we are alive, we are in the way; after death, it will be too late to do it; therefore give not sleep to thine eyes till it be done. [4.] They who continue in a state of enmity to God, are continually exposed to the arrests of his justice, and the most dreadful instances of his wrath. Christ is the Judge, to whom impenitent sinners will be delivered; for all judgment is committed to the Son; he that was rejected as a Saviour, cannot be escaped as a Judge, Rev 6:16, Rev 6:17. It is a fearful thing to be thus turned over to the Lord Jesus, when the Lamb shall become the Lion. Angels are the officers to whom Christ will deliver them (Mat 13:41, Mat 13:42); devils are so too, having the power of death as executioners to all unbelievers, Heb 2:14. Hell is the prison, into which those will be cast that continue in a state of enmity to God, Pe2 2:4. [5.] Damned sinners must remain in it to eternity; they shall not depart till they have paid the uttermost farthing, and that will not be to the utmost ages of eternity: divine justice will be for ever in the satisfying, but never satisfied.

Matthew Henry (1662–1714) — Commentary on the Whole Bible. This section covers verses 21–26. Public domain.
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TertullianAD 220
Of Patience
As regards the rule of peace, which is so pleasing to God, who in the world that is prone to impatience will even once forgive his brother, I will not say "seven times," or "seventy-seven times? " Who that is contemplating a suit against his adversary will compose the matter by agreement, unless he first begin by lopping off chagrin, hardheartedness, and bitterness, which are in fact the poisonous outgrowths of impatience? How will you "remit, and remission shall be granted" you if the absence of patience makes you tenacious of a wrong? No one who is at variance with his brother in his mind, will finish offering his "duteous gift at the altar," unless he first, with intent to "re-conciliate his brother," return to patience.
TertullianAD 220
A Treatise on the Soul
It is therefore quite in keeping with this order of things, that that part of our nature should be the first to have the recompense and reward to which they are due on account of its priority. In short, inasmuch as we understand "the prison" pointed out in the Gospel to be Hades, and as we also interpret "the uttermost farthing" to mean the very smallest offence which has to be recompensed there before the resurrection, no one will hesitate to believe that the soul undergoes in Hades some compensatory discipline, without prejudice to the full process of the resurrection, when the recompense will be administered through the flesh besides.
TertullianAD 220
A Treatise on the Soul
"Love your enemies," says He, "pray for them that curse you," lest such a man in any transaction of business be irritated by any unjust conduct of yours, and "deliver thee to the judge" of his own (nation ), and you be thrown into prison, and be detained in its close and narrow cell until you have liquidated all your debt against him.
Origen of AlexandriaAD 253
FRAGMENT 102.30
In this life, this way traveled by all, you do well to accept and not ignore the suggestions of the conscience. But if you are inconsiderate and negligent in this life, conscience itself, assuming the role of a prosecutor, will accuse you before the judge. Conscience will subject to the juryman’s decision, and you will be handed over to incurable punishments. Such things you would not have suffered, if along the way you had in fact acquired goodwill toward your accuser, accepting his reproaches as offered out of goodwill. For this also the divine Evangelist John says in his letter: “If our conscience does not condemn us, we have confidence before God.”
Hilary of Poitiers (as quoted by Aquinas, AD 1274)AD 367
Catena Aurea by Aquinas
The Lord suffers us at no time to be wanting in peaceableness of temper, and therefore bids us be reconciled to our adversary quickly, while on the road of life, lest we be cast into the season of death before peace be joined between us.

Or, the adversary delivers you to the Judge, when the abiding of your wrath towards him convicts you.

For because charity covereth a multitude of sins, we shall therefore pay the last farthing of punishment, unless by the expense of charity we redeem the fault of our sin.
Chromatius of AquileiaAD 406
TRACTATE ON MATTHEW 22.3.1-2.34
Others, who seem to have a more complete explanation, believe that the opponent here must be understood as the Holy Spirit, who opposes the vices and desires of the flesh. As the apostle points out,“The flesh lusts against the Spirit, and the Spirit against the flesh; for these are opposed to each other, so that you do not do what you would.”The Spirit indeed desires heavenly things; the flesh lusts after earthly things. The Spirit rejoices over spiritual gifts; the flesh is attracted to bodily vices. Concerning this the apostle says, “Do not grieve the Holy Spirit of God, with whom you have been sealed for the day of redemption.” Therefore, the Lord instructs us to listen to this adversary of sin and human error, upholding those things that are righteous and holy. We should obey him in all things while we are with him on the way, in the caravan of this present life. By doing so we will have peace and perpetual fellowship with him.
John ChrysostomAD 407
Homily on the Gospel of Matthew 16
"Agree with thine adversary quickly, whilst thou art in the way with him."

That is, that thou mayest not say, "What then, if I am injured;" "what if I am plundered, and dragged too before the tribunal?" even this occasion and excuse He hath taken away: for He commands us not even so to be at enmity. Then, since this injunction was great, He draws His advice from the things present, which are wont to restrain the grosser sort more than the future. "Why, what sayest thou?" saith He. "That thine adversary is stronger, and doeth thee wrong? Of course then he will wrong thee more, if thou do not make it up, but art forced to go into court. For in the former case, by giving up some money, thou wilt keep thy person free; but when thou art come under the sentence of the judge, thou wilt both be bound, and pay the utmost penalty. But if thou avoid the contest there, thou wilt reap two good results: first, not having to suffer anything painful: and secondly, that the good done will be thereafter thine own doing, and no longer the effect of compulsion on his part. But if thou wilt not be ruled by these sayings, thou wrongest not him, so much as thyself."

And see here also how He hastens him; for having said, "Agree with thine adversary," He added, "quickly;" and He was not satisfied with this, but even of this quickness He hath required a further increase, saying, "Whilst thou art in the way with him;" pressing and hastening him hereby with great earnestness. For nothing doth so much turn our life upside down, as delay and procrastination in the performance of our good works. Nay, this hath often caused us to lose all. Therefore, as Paul for his part saith, "Before the sun set, do away the enmity;" and as He Himself had said above, "Before the offering is completed, be reconciled;" so He saith in this place also, "Quickly, whilst thou art in the way with him," before thou art come to the doors of the court; before thou standest at the bar and art come to be thenceforth under the sway of him that judgeth. Since, before entering in, thou hast all in thine own control but if thou set thy foot on that threshold, thou wilt not by ever so earnest efforts be able to arrange thy matters at thy will, having come under the constraint of another.

But what is it "to agree?" He means either, consent rather to suffer wrong; or, "so plead the cause, as if thou wert in the place of the other;" that thou mayest not corrupt justice by self-love, but rather, deliberating on another's cause as thine own, mayest so proceed to deliver thy vote in this matter. And if this be a great thing, marvel not; since with this view did He set forth all those His blessings, that having beforehand smoothed and prepared the hearer's soul, he might render it apter to receive all His enactments.

Now some say that He obscurely signifies the devil himself, under the name of the adversary; and bids us have nothing of his, (for this, they say, is to "agree" with him): no compromise being possible after our departure hence, nor anything awaiting us, but that punishment, from which no prayers can deliver. But to me He seems to be speaking of the judges in this world, and of the way to the court of justice, and of this prison.

For after he had abashed men by higher things, and things future, he alarms them also by such as are in this life. Which thing Paul also doth, using both the future and the present to sway his hearer: as when, deterring from wickedness, he points out to him that is inclined to evil, the ruler armed: thus saying, "But if thou do that which is evil, be afraid; for he beareth not the sword in vain; for he is a minister of God." And again, enjoining us to be subject unto him, he sets forth not the fear of God only, but the threatening also of the other party, and his watchful care. "For ye must needs be subject, not only for wrath, but also for conscience sake." Because the more irrational, as I have already said, are wont to be sooner corrected by these things, things which appear and are at hand. Wherefore Christ also made mention, not of hell only, but also of a court of justice, and of being dragged thither, and of the prison, and of all the suffering there; by all these means destroying the roots of murder. For he who neither reviles, nor goes to law, nor prolongs enmity, how will he ever commit murder? So that from hence also it is evident, that in the advantage of our neighbor stands our own advantage. For he that agrees with his adversary, will benefit himself much more; becoming free, by his own act, from courts of law, and prisons, and the wretchedness that is there.
John Chrysostom (as quoted by Aquinas, AD 1274)AD 407
Catena Aurea by Aquinas
Or, He here speaks of the judges of this world, of the way which leads to this judgment, and of human prisons; thus not only employing future but present inducements, as those things which are before the eyes affect us most, as St. Paul also declares, If thou doest evil fear the power, for he beareth not the sword in vain. (Rom. 13:4.)
Jerome (as quoted by Aquinas, AD 1274)AD 420
Catena Aurea by Aquinas
The word here in our Latin books is 'consentiens,' in Greek, εὐνοῶν, which means, 'kind,' 'benevolent.'

Some, from that verse of Peter, Your adversary the Devil, &c. (1 Pet. 5:8.) will have the Saviour's command to be, that we should be merciful to the Devil, not causing him to endure punishment for our sakes. For as he puts in our way the incentives to vice, if we yield to his suggestions, he will be tormented for our sakes. Some follow a more forced interpretation, that in baptism we have each of us made a compact with the Devil by renouncing him. If we observe this compact, then we are agreeing with our adversary, and shall not be cast into prison.

And how can the body be cast into prison if it agree not with the spirit, seeing soul and body must go together, and that the flesh can do nothing but what the soul shall command?

But from the context the sense is manifest; the Lord is exhorting us to peace and concord with our neighbour; as it was said above, Go, be reconciled to thy brother.

A farthing is a coin containing two mites. What He says then is, 'Thou shalt not go forth thence till thou hast paid for the smallest sins.'
JeromeAD 420
Commentary on Matthew
(Verse 25 onwards) Be reconciled quickly with your adversary while you are on the way with him, lest your adversary deliver you to the judge, and the judge deliver you to the officer, and you be thrown into prison. Truly I say to you, you will not get out of there until you have paid the last penny. You have heard that it was said to the ancient ones: 'You shall not commit adultery.' But I tell you that everyone. Because what we have in Latin codices is 'consentiens,' it is written in Greek as 'Εὐνοῶν,' which means benevolent or kind. From the preceding and subsequent passages, it is clear that our Lord and Savior, while we run on the path of this world, encourages us to peace and harmony, according to the Apostle, who says: If possible, as far as it depends on you, live at peace with all men (Rom. XII, 18). For in the preceding chapter, he also said: If you bring your gift to the altar and there remember that your brother has something against you: and when this is finished, he immediately adds: Be reconciled to your adversary, etc. And in the following he commands: Love your enemies, do good to those who hate you, and pray for those who persecute and slander you. When this is clear and the consequent understanding, many think it is said about the flesh and the soul, or about the soul and the spirit, which is not entirely correct. For how can the flesh be sent to prison if the soul does not agree, since both the soul and the flesh must be imprisoned together? And the flesh can do nothing except what the mind commands, or the Holy Spirit dwelling in us can deliver judgment to the flesh or the soul that resists, since he himself is the judge. Others, according to the Letter of Peter saying: Your adversary the devil, as a roaring lion, goes about seeking whom he may devour (I Peter 5:8), and the rest, interpret the adversary as the devil, and they want to command from the Savior that, as long as it is in our power, we may be benevolent towards the devil, who is an enemy and avenger, and not make him suffer punishment on our behalf. For since he himself supplies the incentives of vices, and even to us who sin willingly, if we agree with him who suggests vices, he must also be tormented on our behalf. And they say it is a kind act for each saint to sustain his adversary, if he does not make him endure torments for himself. Some say more forcefully that in Baptism each person enters into a pact with the devil and says: I renounce you, devil, and your pomp, and your vices, and your world, which is in the evil one (1 John 5:19). Therefore, if we keep the pact, we are kind and consenting to our adversary, and by no means are we to be shut up in prison. But if we have in fact transgressed anything of what we promised to the devil, we will be handed over to the judge and the officer, and we will be thrown into prison, and we will not be released from it until we repay the last quarter. A quarter is a type of coin that has two minutes. Hence, in another Gospel, that poor and widowed woman is said to have sent a quarter into the treasury (Mark 12), and in another, two minutes (Luke 21). Not that the Gospels are in disagreement, but that one quarter has two minute coins. This is therefore what he is saying: You will not leave the prison until you have paid even the smallest sins.
Augustine of Hippo (as quoted by Aquinas, AD 1274)AD 430
Catena Aurea by Aquinas
(ubi sup.) If this direction be taken literally, it might lead some to suppose that this ought indeed to be so done if our brother is present, for that no long time can be meant when we are bid to leave our offering there before the altar. For if he be absent, or possibly beyond sea, it is absurd to suppose that the offering must be left before the altar; to be offered after we have gone over land and sea to seek him. Wherefore we must embrace an inward, spiritual sense of the whole, if we would understand it without involving any absurdity. The gift which we offer to God, whether learning, or speech, or whatever it be, cannot be accepted of God unless it be supported by faith. If then we have in aught harmed a brother, we must go and be reconciled with him, not with the bodily feet, but in thoughts of the heart, when in humble contrition you may cast yourself at your brother's feet in sight of Him whose offering you are about to offer. For thus in the same manner as though He were present, you may with unfeigned heart seek His forgiveness; and returning thence, that is, bringing back again your thoughts to what you had first begun to do, may make your offering.

(Serm. in Mont. i. 11.) Let us see who this adversary is to whom we are bid to be benevolent, It may then be either the Devil, or man, or the flesh, or God, or His commandments. But I do not see how we can be bid be benevolent, or agreeing with the Devil; for where there is good will, there is friendship, and no one will say that friendship should be made with the Devil, or that it is well to agree with him, having once proclaimed war against him when we renounced him; nor ought we to consent with him, with whom had we never consented, we had never come into such circumstances,

(ubi sup.) I do not see again how it can be understood of man. For how can man be said to deliver us to the Judge, when we know only Christ as the Judge, before whose tribunal all must be sisted. How then can he deliver to the Judge, who has himself to appear before Him? Moreover if any has sinned against any by killing him, he has no opportunity of agreeing with him in the way, that is in this life; and yet that hinders not but that he may be rescued from judgment by repentance. Much less do I see how we can be bid be agreeing with the flesh; for they are sinners rather who agree with it; but they who bring it into subjection, do not agree with it, but compel it to agree with them.

(ubi sup.) Perhaps then it is God with whom we are here enjoined to agree. He may be said to be our adversary, because we have departed from Him by sin, and He resisteth the proud. Whosoever then shall not have been reconciled in this life with God through the death of His Son, shall be by Him delivered to the Judge, that is, the Son, to whom He has committed all judgment. And man may be said to be in the way with God, because He is every where. But if we like not to say that the wicked are with God, who is every where present, as we do not say that the blind are with that light which is every where around them, there only remains the law of God which we can understand by our adversary. For this law is an adversary to such as love to sin, and is given us for this life that it may be with us in the way. To this we ought to agree quickly, by reading, hearing, and bestowing on it the summit of authority, and that when we understand it, we hate it not because it opposes our sins, but rather love it because it corrects them; and when it is obscure, pray that we may understand it.
Augustine of HippoAD 430
I understand who the judge is: For the Father judges no man, but has committed all judgment unto the Son. I understand who the officer is: And angels, it is said, ministered unto Him: and we believe that He will come with His angels to judge the quick and the dead. I understand what is meant by the prison: evidently the punishments of darkness, which He calls in another passage the outer darkness: for this reason, I believe, that the joy of the divine rewards is something internal in the mind itself, or even if anything more hidden can be thought of, that joy of which it is said to the servant who deserved well, Enter into the joy of your Lord; just as also, under this republican government, one who is thrust into prison is sent out from the council chamber, or from the palace of the judge.
Pseudo-Chrysostom (as quoted by Aquinas, AD 1274)AD 500
Catena Aurea by Aquinas
The Lord is urgent with us to hasten to make friends with our enemies while we are yet in this life, knowing how dangerous for us that one of our enemies should die before peace is made with us. For if death bring us while yet at enmity to the Judge, he will deliver us to Christ, proving us guilty by his judgment. Our adversary also delivers us to the Judge, when he is the first to seek reconciliation; for he who first submits to his enemy, brings him in guilty before God.

The officer, that is, the ministering Angel of punishment, and he shall cast you into the prison of hell.

Or, If you will make your peace yet in this world, you may receive pardon of even the heaviest offences; but if once damned and cast, into the prison of hell, punishment will be exacted of you not for grievous sins only, but for each idle word, which may be denoted by the very last farthing.

Or, the prison is worldly misfortune which God often sends upon sinners.
Source: Quotations drawn from early Church Fathers and historical Christian theologians (AD 100–1500). Some quotes address the surrounding passage context rather than this verse alone.
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