Nicodemus Born Again

Q. If Nicodemus was "the" teacher of Israel, why didn't he understand Yeshua when He said "you must be born again?"

A. You are referring to the story in Jn 3.1-10 so let's look at this portion to get some vital information. I believe Nicodemus understood the concept of being "born again" but did not understand the context Yeshua used that night. The concept of "born again" is better understood as "born from above" or from heaven. There was a concept called the "nephesh ha shamayim" or the "soul from heaven" and Nicodemus believed that a person had to be born from heaven. But, he thought that Gentile proselytes needed a new birth, but the Jews didn't need one and what Yeshua said confused him. Yeshua goes on to say that unless one is born of water and the Spirit he cannot enter the Kingdom of God. Another way of saying it is "water which is the Spirit" or born from heaven. The word Heaven in Hebrew is "shamayim" which means "there is water" so you can see where the life comes from. Col 2.16 says that the New Moon festival is a shadow of things to come and this feast is related to being born again. It is called the "Feast of the Born Again" referring to the moon becoming visible again, or "born" again. In Jewish thought, conversion of converts is related to the concept of the womb and grave. Both are the word "kever" in Hebrew and they are related in this way. There is a relation between water and the heavens (shamayim).
Now in the Garden of Eden there were rivers and all water today has its roots in Eden because of the water cycle. So, when one goes into the waters for an immersion he is getting back in touch with the waters in Eden. Immersion connects us to Eden. Yeshua's immersion was a recreation of Gen 1 and it also was connected to His resurrection. Gen 1 was the Creation, Yeshua is connected to the New Creation (born from above). Now, Yeshua was conceived in a virgin (new) womb (kever). At His resurrection he came out of a virgin (new) tomb (kever). So, you can see that an immersion has many concepts to it so that we can understand the spiritual. When one goes into the water he enters into a hostile world. He must come out of the "grave" because he can't live in that water. When he emerges he takes a breath (spirit) and he becomes like one "reborn." The grave is the same word and carries the same meaning and that is why the resurrection is a related concept. When one goes through an immersion there is a "change of status" from the life before. The waters have cut you off from that life and when you get immersed you are actually rehearsing your own resurrection. Being born again spiritually is exactly like that. Yeshua associated the Spirit with being like the wind, in that, the Spirit works when, where and how He wants. He works "unseen" but you know the results. This concept is related to the circumcision of the heart taught in Deut 30.6 and Jn 1.13. All of these concepts Nicodemus understood but he may not have thought it applied to him, after all he was a descendant of Abraham (Mt 3.9). Many Jews believed a Gentile had to be born again but they were "in" because of there ancestry. Yeshua pointed out to Nicodemus that these concepts applied to him as well and this is what confused him.