Jesus was often called ‘Teacher’. It was a term used for rabbis who would impart knowledge to a group of followers. There are many ways in which Jesus proved himself to be a good teacher.
There are five very substantial blocks of teaching material in Matthew's Gospel, which are often called discourses and show the development of the Kingdom of God theme. The first is the Sermon on the Mount, in Matthew 5, 6 and 7 about the lifestyle of the Kingdom, covered by the whole of Series 4 of Word Online. The second is in Matthew 10, Series 6 Episode 2, which is about mission in the Kingdom The third discourse is in Matthew 13, in the form of seven parables, Series 5 Episodes 8 -12, in which the overall theme is the growth of the Kingdom. In Matthew 18 - the theme is the community of the Kingdom, Series 7 Episodes 6 - 10 and the fifth discourse is about the future of the Kingdom, Matthew 24 and 25, Series 12 Episodes 1 - 7.
It's not surprising that Jesus used similar stories and similar teachings in different contexts. It's something that you'd expect of a great teacher. We see quite a number of examples of this in the Gospels - one would be the parables of the Great Banquet, Luke 14:1 - 24 Series 9 Episode 2, and the Wedding Banquet, Matthew 22:1 - 14, Series11 Episode 8. Although on both occasions, Jesus was teaching with the backdrop of the conflict between him and the Jewish leaders, the circumstances are different as are several elements of the storyline. In Luke Jesus was travelling south towards Jerusalem having left Galilee, and in Matthew he is in Jerusalem in the last week of his earthly ministry.
Jesus knew that you have to give people as much truth or information that they're capable of dealing with at one time and you have to give people time to absorb information, especially difficult things. One of the things that he knew would be difficult for his disciples to grasp was the concept of him dying and then rising again from the dead. He needed to spend a lot of time preparing them for this reality. Jesus started to do this at the time when he left Galilee, at the time of his transfiguration, Matthew 16:21 - 28, Series 7 Episode 2. He began to warn his disciples that he would go to Jerusalem, that he would suffer, die, and be raised again from the dead. He'd die at the hands of the authorities. At that particular time, the disciples were completely confused by that. They didn't believe it. They didn't understand. They didn't really know what he was talking about. Jesus knew he had quite a difficult task ahead of him. He speaks to them more often about this and more fully during the last supper he shared with them, John 14:1 - 14, Series 12 Episode 13; and John 16:16 -33, Series 12 Episode 17.
One of the ways Jesus helped his hearers to remember his teaching was through the use of parables. Although Jesus’ parables are drawn from everyday things, they deal with important themes like the Kingdom of God, the importance of prayer and the meaning of love. Jesus’ listeners could identify with the farmer whose neighbour sowed weeds amongst his wheat Matthew 13:24 - 30, Series 5 Episode 9, and the woman who lost a coin, Luke 15:8 - 10, Series 9 Episode 4. They knew the road from Jerusalem to Jericho and the likelihood of mugging there, Luke 10:25 - 37, Series 8 Episode 8. Jesus also used simple imagery in his teaching, like bread John 6:35, Series 6 Episode 7 and shepherding John 10:1 - 21, Series 8 Episode 6.
BUT . . .
Jesus is not just a moral teacher, prophet, healer, or a kind and loving man - he was all those things - he is far more than all of those things put together. He is the promised King of the Old Testament; the unique Son of God; and the Saviour. Luke 1:26 - 38, Series 1 Episode 5.