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Why did Jesus often break the Law?

Never did, broke foolish oral additions by Pharisees, such as the Korban teaching which let them break the 4th commandment. He said He came not to destroy but to fulfill.

Did Jesus contradict Paul - Jesus said He came to fulfill law, Paul said we are free from law.

Paul meant that keeping law does not earn salvation, though breaking it can earn punishment: Rom 6:23. Jesus said same in saying we must be like little children, who get things because parents are good, without earning it, though they could earn to lose inheritance.