The point is that how "cool" something is is supposed to track the potential value there

Nope. How useful something is is supposed to track the potential value. If I were to go meta, I'd say that "cool" implies a particular kind of signaling to a specific social sub-group. There isn't much "potential value" other than the value of the signal itself.

It seems like you see me as implicitly asking "why do you guys keep making pieces instead of going on an adventure!?!?!"

Still nope. Most people don't want to go on a real adventure -- it's too risky, dangerous, uncomfortable. Most people -- by far -- prefer the predictable job of producing the pieces so that they can pay the mortgage on their suburban McMansion. In the case of academia, going for broke usually results in your being broke (and tenure-less) while a steady production of published papers gives you quite good chances of remaining in academia. Maybe not in the Ivies, but surely there is a college in South Dakota that wants you as a professor :-/

"you must produce the pieces". Really?

If you want tenure, yes. If you don't want tenure, you can do whatever you want.

then you should probably at least ask what your chance of winning the million is before settling for $500.

Sure. The answer is a shrug and if you want a verbalization, it will go along the lines of "Nobody knows".

so they are going to end up stuck as pieceworkers even if there's a way to have much much more"

There is no way for all of them to "have much much more". Whether you think the trade-off is acceptable depends, among other things, on your risk tolerance, but in any case the mode -- the most likely outcome -- is still of you losing.