On a personal level, one of the greatest gifts God gave me were my parents. My father's parting words to me when he dropped me off at college were: "You are now responsible for making your dreams come true." The message was clear: Anything I wanted in life, from the moment they drove away, I had to earn on my own. Some of my friends thought it was cold, yet it was liberating, exciting - and, yes, scary. I knew that he had just handed the keys over to me, so to speak, and I wanted to make him proud. Even today, I sometimes say it aloud to myself when we are working on launching a new business or taking a risk in one field or another.
When people behave as you described, they are often unable to stay in one place for long. This includes employment, friendships, and family relationships. Although far from perfect, it's nearly impossible to fool everyone all of the time. In the end, he'll usually end up getting what he deserves.
Another possibility is the idea of where in an economic system one's skills reside. Typically, by the time I see a man or woman, they've had to acquire some pretty impressive skills, either in graphic art, coding, or finance (almost everything else, we can teach). Someone who has a sense of entitlement probably didn't make it through that far so I'm not sure I get to see this side of my age group because of the natural filtration that exists in my industry. It also helps that our business model allows us to work only with people I like, admire, and trust. In other words, if I were operating a call center business, I'm sure I'd have plenty of experiences dealing with the type of person you described because the "barriers to entry", in economic parlance, are relatively low. It's also possible that whoever did the hiring at your firm was just a dumb*ss, if you'll pardon my candor. That's why I love pay for performance models. People should be judged solely on what they accomplish - not on what they know, what their resume looks like, or who they've worked for in the past. Rockefeller was a clerk at a commodities firm in Ohio. Carnegie worked as a telegraph operator. Their resumes were not impressive until later in life, when their accomplishments made them stand out from the crowd.