So what was it that Nicodemus was supposed to understand from these famous words of Jesus? Almost undoubtedly, when Jesus speaks these words about the lifting up of the Son of Man, he is being self-referential. However, two thousand years of familiarity with the story of Jesus should not be allowed to cause one to imagine that the self-referential nature of the statement was supposed to be immediately clear to Nicodemus. To think such a thing would be an unreasonable assertion on the part of the reader.
Additionally, to treat Nicodemus as anything less than a well-learned, well-respected individual, simply because of what seem to be odd responses on his part to the questions and statements that Jesus is reported to be putting to him, would be an unwarranted reading based on theological and doctrinal pre-suppositions (and unfortunately ill-informed prejudices), along with the tangible benefit of the theological treatise of the Gospel of John, back on to the Scriptures.
One of the bottom lines that must here be recognized is that Nicodemus is no fool, though some want to take the path of portraying him as such. When he is first introduced into the story, he is identified as a Pharisee. Not only that, the reader is informed that he a “member of the Jewish ruling council” (John 3:1b). Too often, a caricature of Nicodemus as something of a less-than-fully-aware fool in the presence of Jesus, produces a similarly unfortunate caricature of the Jewish ruling council, all of which were too dense to recognize what was slapping them in their face in the person and ministry of Jesus. It is to be remembered, that even Jesus’ disciples are shown to have failed to grasp who and what Jesus was.
So as a Pharisee, Nicodemus would not only have been well-versed in the history of Israel, but he would have also stood as a guardian of its covenant-related identity markers. At the very least, he would have seen himself as a guardian. Accordingly, he would have been very much concerned and very much looking forward to the time at, and the means by which, Israel’s God would intervene on behalf of His chosen and faithful people, delivering them from their long-running exile (foreign subjugation, which was connected to their God’s curses upon His people for their failure to obey His commands and to fulfill His purpose for them).
As a Pharisee, and therefore as a member of the group of people that was informally charged with the maintenance of the faithfulness of the people when it came to the marks of Jewish identity (covenant markers: circumcision, food and purity laws, Sabbath-keeping), it is likely that he would have found the existing situation, with Israel suffering under the oppressive heel of Rome and its Caesar, to be an untenable and highly undesirable circumstance. This was likely to have been the case regardless of how many benefits Rome might bring (or claim to provide), and no matter how much “freedom of religion” was offered to them by their Roman overlords. Ultimately, anything short of total autonomy, with Israel ruling itself and determining its own place in the world, was unacceptable.
As a member of the Jewish ruling council, Nicodemus would have been in an officially sanctioned position of religious and civil influence among the people, walking in the world of Judaism (religious) that was somewhat desperately attempting to keep the people faithful to their covenant God as they lived in a state of great expectation, while also attempting to keep those same expectant people from running afoul of Rome and its power (civil), while they awaited another exodus (with the foreign powers leaving the land of Israel this time) similar to that which Israel experienced under Moses.