I don't think this is all just related to a lack of ambition, either. Prager's observations reflect something that I've observed over the last few years when dealing with people in various industries. It's what I call an "unqualified upward migration" of workers in many industries -- caused by what is basically a serious lack of qualified people in jobs that used to be considered highly respectable in the past.
A perfect example would be the three bank branch managers I've dealt with over the last 18 months for various needs I've had related to my business. None of them was able to help me address something I thought was a relatively simple issue. By the time I dealt with the third one I realized what the problem was: A few decades ago, these people would have been working as clerical staff at a doctor's office or a small local business. Today, they're considered branch manager material in the banking industry.
I think Dennis Prager has been dealing with car salespeople who should be working in the fast food industry.
Re Bankers:
Women work cheap and follow the book with no thought getting in the way
The Peter Principle lives!!
What you describe is supposed to be the great success of our economy—fewer menial jobs (for non-illegals, that is), with everyone being able to aspire to and enter the middle class.