Agree with your adversary quickly, while you are in the way with him; lest at any time the adversary deliver you to the judge, and the judge deliver you to the officer, and you be cast into prison.
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Augustine of Hippo
AD 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.
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.
& 26. Agree whilst you are in the way, or wayfaring men, i.e. in this life, lest you be cast into prison, i.e. according to Sts. Cyprian, Ambrose, and Origen, into purgatory; according to St. Augustine, into hell, in which, as the debt is to be paid to inflexible justice, it can never be acquitted, and of course no release can be hoped for from that prison. (Haydock)
Having mentioned first the judgment, then the council, then hell, and having spoken of his own sacrifice, Jesus then adds, “Come to terms quickly with your accuser while you are on the way to court.” That is, don’t be saying, “What if I am the injured party? What if I have been plundered and dragged before the tribunal?” Even this kind of circumstance fails to qualify as an excuse or occasion for refusing to be reconciled. Jesus commands us even in these circumstances not to be at enmity with others. Then, since this command was so significant, he illustrates his counsel with examples drawn from daily affairs. Less intelligent people, after all, are more apt to respond to present realities than future ones. “What is that you are saying?” he asks. “So your adversary is stronger and has wronged you? He will wrong you even more if you don’t make it right and he ends up taking you to court. In the former case, by giving up some money, you keep yourself free. Once a judge has passed sentenc...
That is, that you may 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 has 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 do you say? says He. That your adversary is stronger, and does you wrong? Of course then he will wrong you more, if you do not make it up, but art forced to go into court. For in the former case, by giving up some money, you will keep your person free; but when you have come under the sentence of the judge, you will both be bound, and pay the utmost penalty. But if you avoid the contest there, you will reap two good results: first, not having to suffer anything painful: and secondly, that the good done will be thereafter your own doing, and no longer the effect of compulsion on his part. But if you will not be ruled...