And to whom would you lay the blame of creating the atmosphere of entitlement? Is it a construct that Millenials decided to work up through their Elementary, Junior, and High School educations? It doesn't seem rational to point out 'entitlement' without context as to where such a trend came from. Would you agree the Baby Boomer "Me Generation" set up the stage for what we're seeing today?
The OP's argument was ridiculous enough that we don't need to start pointing the finger at who is to blame for what. Inter-generational flame wars between millenials/boomers/etc are likely to just waste a lot of people's time without contributing a great deal of insight.
But who set the stage for the Baby Boomers? Do we blame the previous generation for that?
At some point, you need to take responsibility for your own actions. Even if the situation that you're in isn't your fault, it IS up to you what you do to get out of it.
So you do agree there's context that is important? To answer your question, yes, absolutely look through history for understanding how "The Greatest Generation" could breed the "Me Generation" and now here we are.
To put it another way, the US political and economic system is a giant game of Jenga, and by the time Millenials have showed up, the tower is rife with holes, wobbly, and on the brink of failure - these weren't the actions of the Millenials, but yet claims like yours seem to pass the buck in a blase fashion.
My argument is that the context is irrelevant. You have to do what you can with the hand you're dealt, but ultimately, if you're not willing to work for things, you will be poorer than someone who is.
I also find it ironic that you use the term "pass the buck".