Understanding that the proper time had arrived in God’s plan, Matthew chapter 21 chronicles how Jesus arranged his entry into Jerusalem in a manner which identified him as the Messiah prophesied in Scripture (Zechariah 9:9, Matthew 21:1-9). Once in the city, Jesus began publicly interacting with the people. These actions quickly drew the attention of the religious leadership, who responded negatively to Jesus’ words and claims. This began a series of exchanges between Jesus and representatives of the religious leadership, some of which are recorded in Matthew 21:15-16, Matthew 21:23-46, Matthew 22:15-22 and Matthew 22:23-33. 

In each case, the representatives questioned Jesus’ authority or tried to trick him into responding to questions or hypothetical situations in a manner which would, in their minds, expose him as a false teacher in front of the people. In each case, Jesus provided answers and rebuttals which not only demonstrated his understanding of the wording and spirit of the Scriptures but also caused the selfish and haughty intentions of the leadership’s representatives to be revealed.

Matthew 22:34-46 record another instance of this type or encounter between Jesus and the religious leadership. In a further attempt to discredit Jesus in front of the people and reassert their own authority, the leadership representatives asked Jesus a deceptively simple question (Matthew 22:36) – What is the greatest commandment in the Law?

After agreeing to become God’s chosen people (Exodus 19:8), God gave a series of laws and instructions to the people of Israel, as recorded in Leviticus, Numbers and Deuteronomy. Further, over the following generations, God also worked through specific individuals who came to be known as “prophets,” to deliver important messages and sometimes warnings to the Israelites. Among these were prophets such as Isaiah, Elijah, Jeremiah and Zechariah. By Jesus’ time, these laws, instructions and words of the prophets were recorded, and collectively became the scriptures that served as the foundation that the various sects of the Jewish religious leadership, such as the Pharisees and the Sadducees studied, interpreted and communicated to the people.

When the Pharisees asked Jesus what the greatest commandment of the Law was, they were referring to the scriptures that recorded these laws, instructions and prophecies. By asking such an open-ended question, the Pharisees attempted to draw Jesus into a debate which the Pharisees could conceivably twist to their advantage. Jesus avoided this trap, answering that the greatest of God’s commandments were to first love God with all one’s heart and mind, and secondly, to love one’s neighbor as oneself (Matthew 22:37-39). He concluded this statement saying that all of the scriptures that the Pharisees had dedicated their lives to (the laws and instructions given to Israel by God when they agreed to become His people combined with all of the messages that God had sent to them through prophets) depended, or “hung,” on these two commandments. By focusing for so many generations on the minutiae of the scriptures, and by using their positions of interpreting them to elevate themselves above the people, love for both their fellow Israelites and mankind was missing from the hearts of the Pharisees. Jesus understood the depths of God’s love for mankind (John 3:16) and used the situation that the Pharisees had orchestrated to emphasize the importance of love in those seeking to please God.

Additional Resource:
Christian Questions Podcast
Episode #1318: “What Did Jesus Really Think of the Pharisees? (Part I)”
How Jesus exposed the deep hypocrisy of the scribes and Pharisees
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CQ Rewind Show Notes