What is it about the righteousness of the Pharisees and teachers of the law that Jesus referring to here? Is it different from the righteousness of a true disciple of Christ?
AMP - 20 For I tell you, unless your righteousness (your uprightness and your right standing with God) is more than that of the scribes and Pharisees, you will never enter the kingdom of heaven.
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In my opinion, what Jesus was referring to here pertained to a person's true attitude (as contrasted with the person's claimed attitude or apparent actions). The Pharisees and teachers of the Law of whom Jesus was speaking were scrupulous about complying with even the smallest external or visible requirements of the Law, and made a point of ostentatiously displaying their professed devotion to God in public (through such means as the wearing of external ceremonial ornamentation, or the offering of long public prayers), so that others would praise them for their perceived piety, and give them places of honor at public functions. However, while doing this, their underlying motives, rather than being based on love of God and love of their neighbor (which, as Jesus said in Matthew 22:37-40, summarized the whole of God's Law), were characterized instead by greed, injustice, and a total lack of mercy toward the slightest failings of others. And, at the same time, they overlooked the ways in which they themselves were violating the intent or spirit of the Law, and did not recognize their own need to repent and seek God's mercy and forgiveness for themselves. To put it briefly, they were hypocrites. (Jesus elaborated on this in Matthew 23:1-31.) By contrast, the righteousness of true disciples should be characterized, first, by humility and a recognition of their own sinfulness and need of God's forgiveness in Christ, and then by subsequent actions of love toward others, motivated by gratitude to God for the mercy that He has shown in forgiving them for their own imperfection for Jesus' sake, and reflecting the love that God has shown to them in doing so.
The Pharisees, as Jesus says, wash the outside of the cup, but the inside is filthy. When Jesus says that unless our righteousness surpasses that of the teachers of the law we won’t enter heaven, He means that unless we are cleansed and repentant in our hearts, we won’t enter heaven. He explains this rather well when He says “Anyone who looks at a woman lustfully has already committed adultery with her in his heart.” So while one may look holy and righteous on the outside, it means nothing if the inside is not washed.
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