OK, as a former NYPD supervisor, in charge of lots of inexperienced rookies, I used to tell all the cops I was in charge of the same thing----if you call me to the scene, you better have the right answers.
And if you don't have the right answers, find an experienced officer and bounce the issue off him before calling me, because once I am called, and you give me the details, I am going to go by what "the book" says gets done.

The supervisor was trying to coax you towards the proper answers that get you the chip and doesn't put him in a position of breaking a rule. IMHO, he could have just said "sorry, no can do.".

Is it silly? Probably. But that is the way the game is played.

Going forward, I would smile and say "Yes, I am going to play", take the chip, and walk away. Doubtful they will say anything, but if questioned for walking away, I would say I want to go eat something and think about my strategy a minute before playing. Or something like that.