I didn't understand it when I was 12, but I get it now. Jack's total lack of awareness that is common amongst the super-rich, the exploited low-level workers, the nepotism, and, by extension, hypocrisy of Maya. Really put into perspective that not much has changed in 23 years in the workplace.
One recurring joke is “New York is a tough city” when characters are in financial pickles, and the utter tone-deafness of that joke makes it a perfect example of the disconnect in reality of the elite, then and now.
It has a very “let them eat cake” vibe to it.