I think the difference is that it’s a lot easier to disregard or set aside concerns about an ambiguous future. It strikes me as similar to the phenomenon where many sports stars end up bankrupt after their careers – while playing, they certainly have enough money to invest to keep them going for the rest of their lives, but something about the hypotheticalness of an ambiguous future interferes with that calculus.
On the other hand, if you tell a player “you will be benched if X happens” while simultaneously telling them “you will be traded if not-X happens” the dilemma gets a lot more acute.
