Rather than looking upon this sharing of the best wine at the latter end of the wedding feast as an act of considerable generosity and thoughtfulness on the behalf of this bridegroom, which some may be prone to do, this would be readily perceived as a slight to his honored guests. Questions would arise. Why was it that they not receive this wine? Why was it that they were not thought to be good enough to receive these superior libations?
It would be wondered why the bridegroom was mocking his guests in this way. Rather than being enjoyed by the elites and those in the community that possessed the most honor according to the court of public opinion and reputation, the best wine is now going to be enjoyed by the servants and less honored guests, thus putting those that were less honorable on the same level as the honored guests. Worse still, what this would have accomplished at the level of perception (which is what mattered), this elevated those that were possessive of less honor above the honored guests, which could be perceived as an insult to honor, thereby becoming a source of conflict for the bridegroom and his family (as well as the family of the bride).
The head steward, as indicated by the presentation of the author of the text, comes to realize the dynamics that are now at play. It is interesting that the author includes the information that the head steward of the feast did not know the source of the wine (John 2:9), and it is upon his tasting of the wine that he is spurred into action. The actions that follow, which are often interpreted as his commendation of the bridegroom, can only be so interpreted outside the context of cultural meal practice and the social constructs that are on display in the meal.
Rather than interpreting his actions in this way, what can also be realized is that the head steward, as he thinks about all of the problems that have now been presented to both him and the bridegroom due to the revelation of this new and better wine that is now being served at the end of the meal, must take quick action on his own behalf, so as to preserve his own place of honor and standing in the community (whatever that may have been). If he does not take these actions, it is he that runs the risk of being shamed, and this is what can be understood to be playing out in the story.
The head steward, of course, is the master of the feast. Chief among his duties would be the duty to see to it that the most honored guests had received the best wine and the best food. This is crucial. Now, unbeknownst to him, and certainly without his approval, the best wine is going to go to the guests at the lower end of the honor spectrum. Among other things, this would mean that the head steward had not done his job, thus he would be shamed (though this shaming would not stop with him).
Thinking quickly then, the steward makes his way to the bridegroom and says “Everyone serves the good wine first, and then the cheaper wine when the guests are drunk. You have kept the good wine until now!” (2:10) Again, one must resist the temptation to think of this as simply a matter of the head steward offering some type of praise to the bridegroom for his unexpected generosity. This is much more likely to be the head steward’s attempt to shift the negative reactions that are sure to come, along with the associated dishonoring that is bound to take place, on to the bridegroom and away from himself.