Why did Jesus point out Israel’s failures, the hypocrisy of religious leadership/the Law Covenant, repeatedly, during His ministry?

The focus on the Old Covenant by Jesus was integral with His efforts to incrementally move His ministry, initiated in Law as He was born under the Law, into a ministry of grace that is actuated by faith, alone, in Him as Messiah, alone. A New Covenant where obedience is made possible through the indwelling Holy Spirit and the production of divine fruit as opposed to keeping arduous rules and regulations that the sin-nature was not able to uphold.

Jesus points out the failures of the Old Covenant and its representatives, the Pharisees and the Sadducees, the Council members…these represented the worst of what the Law had to offer; that is, through these religious leaders, Jesus demonstrated the perils of law via subjectivity, rationalization, hypocrisy. These are resultants of the Adamic sin-nature seeking righteousness through law keeping.

The sin-nature, integral with the pride and arrogance of man, easily and quiet effectively, rationalizes away, justifies away, obfuscates, what the conscience seeks to arbitrate toward holiness and righteousness. Moral relativism is a huge failure of codified law and spiritual law.

Jesus’ ministry, the New Covenant, the Gospel, is oriented toward a New and LIVING Way to walk in obedience to the Father’s will as we are prepared for service in the New Jerusalem via daily Christian sanctification (Galatians 5:16); that is, in the New Covenant, the focus is upon the indwelling Holy Spirit who is given to the redeemed in Jesus as their personal Guarantor and Seal of New Covenant promise (Ephesians 1:13-14; Hebrews 8:12).

It is through the Spirit’s work in daily Christian sanctification where He anoints the redeemed in Jesus with a new and enlivened/sensitive conscience, the “new creation” (2 Corinthians 5:17), it is the new man that is made exponentially aware of the Father’s will and that will is expressed and satiated through the production of divine fruit (Galatians 5:16-23) and it is this fruit that wonderfully and successfully fulfills all law; both, codified and spiritual (Galatians 5:23); this divine fruit of the Spirit actually pleases the Father and proves one to be a disciple of Jesus (John 15:8). This divine fruit will also stand the test of authenticity at the BEMA Judgment of Messiah.

If you study Messiah’s ministry carefully, you will see a subtle, incremental, steady, transition from “keep my commandments” (John 14:15) to “produce much fruit” (John 15:8) and Jesus also teaches that it is “fruit” that differentiates between teachers of divine truth and wolves in sheep’s clothing (Matthew 7:16).

This subtle move in Jesus’ ministry is further expounded upon by Jesus’ minister of the Gospel to the Gentiles, Paul…who teaches that the redeemed are no longer under letters of condemnation weakened by the sin nature (Romans 8), but the redeemed are led by the Spirit to produce divine fruit (Romans 7:6).