What does Matthew 23:37 mean?So far as the gospel of Matthew is concerned, these are the last words Jesus will speak to Jerusalem in a public setting. He has more yet to teach, and the two chapters will contain extensive records of those words. This, however, is the point where Jesus' public ministry ends (Matthew 23:39). Prior to this, Jesus has been condemning Israel's failed religious leadership (Matthew 23:1–3). Those words were delivered with a cutting, direct mood. Here, Christ's words are significantly more mournful. Looking ahead to the disaster that will come on the city, Jesus speaks with a tender and longing tone.
Despite being the chief city of God's chosen people, Jerusalem has earned a sad legacy over the generations (Acts 7:52). This city of David has become known as the city that kills prophets and stones the messengers God sends to her. That legacy will be emphasized eternally within the week as Jesus Himself is condemned and killed in Jerusalem (Matthew 26:1–5).
Jesus describes the role He would have rather held in relationship to the city and the people of Israel. Speaking from the perspective of God, as a member of the Trinity, Jesus notes how often He would have stepped in to protect Jerusalem and her children. The symbolism here is unique in Scripture and carries an almost maternal sense. Jesus, the Son of God, describes His heart motive to protect His people.
Of course, since God is omnipotent, that raises the question of why God did not, in fact, offer that level of protection. Why did they suffer so much judgment and death? Why will the city be exposed to the destruction yet to come (Matthew 24:1–2)? The answer is not complex, though it can be hard to accept: the people were not willing to receive His protection. They rejected God, and His messengers, and His message (John 5:39–40). And so, judgment fell, and would soon fall again.