"If you don’t have a dime to your name you should take the guaranteed million dollars all day, every day. But what if you have some money? What if you’re already a millionaire? At that level of wealth taking the 50/50 shot at $50 million might be far more tempting."
A wealthy person, could, for example risk buying an older used car that would potentially need costly repairs. In case it needs these repairs, they will suffer some financial losses but would still be able to derive utility from the car. In case it doesn’t need them, they get rewarded for the risk with a functional car that costs considerably less than a new one.
For a broke person the same decision is much harder. Not being able to repair the car would unlock undesirable 2-nd and 3-rd order effects, like, not being able to go to work.
Prizes for challenges, maybe. Chess tournaments with a buy-in, that I respect because no luck involved, meaning no tipping the scales no cheating.
So the problem in gambling is when you just lost a big bet of money you didn't need and the only way to recover is putting up a tiny bit of money you do need. By nature gambling--and by the way it's sold--is designed to fuck with that fine line.