Imagine a small business person not well-known or highly-regarded in the community, considered uneducated by the academic class of the time, suddenly chosen by the greatest teacher of all time. Imagine such a person being a hand-picked apprentice of someone with the wisdom, power and authority of Jesus.
Jesus takes the time to explain to you and your fellow apprentices what he either does not or can not explain to the larger crowds. It must be amazing and scary.
After he teaches a few parables to the crowds, he explains them to his disciples. He asks them if they understand. Jesus wanted to ensure that those he had chosen understood his teachings. Why? Because these uneducated men were entrusted by Jesus to pass these teachings about the Kingdom of Heaven to others.
I'm not sure they fully knew that when Jesus talked about "experts of the Law discipled in the Kingdom of Heaven" that Jesus was talking about them. They probably immediately thought of scribes and rabbis they personally knew. But Jesus called these uneducated (by Rabbinic standards) men, experts of the Law. What an extraordinary statement.
Understand that most Jews knew the Law. For the Jew, the Law is everything. It is how they related to their God and how they lived their lives. So even these uneducated men had some rudimentary knowledge of the Law. But Jesus now calls them experts. How?
"Therefore every scribe who has become a disciple of the kingdom of heaven is like a head of a household, who brings out of his treasure things new and old." The treasure is the revelations of the King. The treasure is heavenly wisdom. The old is the Law. The new is the Kingdom of Heaven. According to Jesus' teaching, the new doesn't make the old obsolete, but the old enhances the new. Jesus brought a perspective to the Law through the Kingdom of Heaven that only his disciples truly understood. Therefore, they are the new experts in the Law.
"Repent for the kingdom of heaven is at hand." Understanding the kingdom of heaven and coming to trust completely in the King is everything. Father, may all of us who have become a disciple of the kingdom of heaven wisely and generously dispense the treasure you have entrusted to our care.