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Matthew 5:25-26 meaning
The parallel account of this teaching is found in Luke 12:57-59.
Jesus shares a second example of earthly relationships. But instead of sacrifices upon the altar in the temple, He shifts the setting to a legal courtroom. And in this instance, it is not a brother but rather an opponent at law in the dispute. The four people in His example are you, your opponent at law, the presiding judge, and the officer of the court. The example makes it clear that guilt is not in dispute, you know you have wronged your opponent.
Jesus makes a clear command. He says to make friends (reconcile) quickly (with urgency) with your opponent at law. He tells His disciples to do this while you are with him and on the way (v 25). The phrase while you are with him means "right now" (v 25) On the way means on the way to trial. Don't wait until later, and don't wait until the trial. Make restitution with a sense of urgency.
This applies to our current life. It is always better to seek harmony and settle when possible, rather than "go to court." In this story, it is clear we are guilty; Jesus tells us we will be thrown into prison if we stand trial before the judge (v 25). Therefore, our reason to go to trial would be to avoid paying what we owe. To try to shirk our responsibility. Jesus counsels to take responsibility and make things right promptly.
Jesus presents two options. We can make friends with our opponent and reconcile with him by making right the wrongs we've done against him. If we choose this option, we avoid the negative result of the court.
The alternative is to choose not to make amends with our opponent now and ignore the wrong we have done him. But justice is still inevitable. When we stand trial, when the judge finds us guilty he will hand us over to the officer, and we will be thrown into prison (v 25). If we are thrown into what is apparently a debtors' prison, Jesus warns with His divine authority Truly I say to you, that we will not come out of there until we have paid up the last cent that we owe (v 26).
It is far better to choose the first option and pay what we owe than to try to avoid payment and find out the judge's verdict after the fact. The key to following this kingdom advice would be to have the objectivity to see our own actions truly; in particular that we are in the wrong. Humans are excellent at self-rationalizing. To follow Jesus' command here requires objectivity toward ourselves. Another key is to shoulder responsibility for our actions. We can't follow this instruction while placing blame on others.
This teaching could also apply to the day of judgment. There is another trial we are all on the way to attending. That is the judgment seat of Christ (2 Corinthians 5:10) where we will give an account for the things we have done, said, and harbored within our hearts. It seems clear there will be a price to pay for the known wrongs we have done. The things we remember but did not act upon. The Lord's Prayer will make settling our debts with others a priority. 1 John 1:9 tells us to confess our sins before God, and He will forgive our sins, and cleanse us. Just as the disciples had only to have their feet washed to be clean, Jesus will "cleanse us from all unrighteousness." If we confess our sins now, we will avoid a negative consequence from the judge.
It seems clear it is better to seek restitution now and avoid answering for our offense when we stand trial before God (1 Corinthians 3:11-15).
When we consider this passage together with the verses preceding it (Matthew 5:21-24) we see that righteousness (harmony) applies to our external obedience to the commandments (Do not murder) and to our internal obedience (do not be angry.) We also see that how we treat others affects our present fellowship with others, as well as with God and our future Kingdom prospects at the Day of Judgment.