This passage is not without context. Jesus is embarrassing the Scribes and Pharisees for their moral hypocrisy. He has entered upon a list of issues in which the Jewish leadership have defied God’s revelation going all the way back to Eden. If you attempt to stand these teachings as stated in our modern Western context, you will seriously miss the point. They are not free standing absolutes; they exist within the context of a nation Jesus seeks to restore to her covenant with God.
In these ancient principles, we see the first step toward salvaging the human condition from the Fall. They provide an initial warning, a minimal boundary that gives notice that we are sinners, because we don’t even want to obey these, as easy as they are. This is how they were supposed to be understood. Those whose hearts were awakened by these low boundaries would then turn inward and seek to understand the wretched condition of their souls and cry out for redemption. We’ve been given a glimpse at the murderous hatred and uncontrollable lust of the flesh. The Scribes and Pharisees looked for ways to circumvent even these primitive warnings, and claimed that God approved of their ways.
For example, they were notorious for making high sounding oaths to Jehovah that turned out to be empty. It was carefully worded so that they were not actually bound by anything. Anytime one of them swears generously like that, you need to run the other way, because they will stab you in the back. Jesus notes that from ancient times it was forbidden to make an oath before God and not carry it through. There was a reverence for avoiding blasphemy and defaming God in the presence of other people. However, it was widely known that Scribes and Pharisees kept a list of legalistic word choices that were legally binding, and plenty that were not.
Jesus says flatly that the whole business is blasphemous. Why would you need an oath in the first place? Just do what you say consistently, and no one will ever need to ask for an oath. They’ll know you honor God from your heart regardless of the context.
Who could forget the ancient Law of Retaliation? It was a remarkable achievement in restoring balance between feuding parties, each demanding a premium recompense for some slight. Very early in human history it became the law of great rulers to squash that nonsense and demand penalties that equaled the offense, and nothing more. Thus, if you poked out someone else’s eye, they could demand nothing more than your eye be poked out. No escalation was permitted.
Jesus said that you should drop the pretense of privileged victimhood. This life is not worth anything in the first place, so trying to break even in human terms will divert you from the path back to Eden. If you are determined to find God’s throne, then don’t waste time chasing the anxieties of human existence. People who belong to Heaven aren’t much worried about the bumps and bruises that pitiful lost souls dish out.
Is someone else in such desperate straits that they’ll take part of your clothing? Give them all but your underwear. God will provide for your covering. If someone is going to use Roman Law to make you carry his military gear a mile, carry it another mile to show that you value something else much higher than mere convenience. Do it as unto the Lord. Give to beggars and those who always borrow but can’t repay. Your Father will provide what you need for His purpose in Your life. Show the world that you belong to a higher plane.
It’s like another ancient instruction that you should love your neighbor and save your spite for enemies. This is the foundation for much of the Covenant: Your fellow Israeli is your family. If you can’t love at least some people, you are dead already. Even tax collectors are friends with people friendly to them. The Scribes and Pharisees were notorious for despising everyone who wasn’t part of their in-group. There was a modicum of public respect for their fellow rabbis, as long as they struggled to excel within the artificial rabbinical system. But behind the scenes, they were downright vicious with each other over the smallest petty insults. They looked for ways to skirt their obligations under the Law of Moses on such things.
Jesus says the Law is just the starting point. Do you want to please Your Heavenly Father? Find a way to love even your enemies. Nobody says you have to tolerate the destruction of shalom, but you need to understand what peace with God actually is. When you show that your love is stronger than human hatred, your enemies will be hammered with conviction for their sins (Jesus said elsewhere).
Do you notice how God treats those who hate His commands? He sends the same rain on the just and unjust. Think about how you can emulate that. There are some measures of respect and kindness that simply apply to humans that God has put in your life; you are supposed to offer care on His behalf. God is like any other ruler, in that He proposes minimum standards to keep everyone in His realm from killing each other. However, those who serve in His court are a cut above that sort of gutter justice.
People with genuine conviction tend to go beyond what’s required of them for peace. I’ve seen this quality in good leaders. One _could_ get justice for wrongdoing against them and still be in the right, but if they are moved by those convictions, scandalous forgiveness can happen.