But what if he didn’t “give up” the $100?
What if it was just lost and he doesn’t know how to get it back?
Famously, the Brisker Rav said that we have up Moshiach for the medinah.
If that’s the case, he may indeed enjoy his lollypop.
But what if the lollipop is unhealthy or treif?
Also: http://www.theyeshivaworld.com/coffeeroom/topic/popa-figures-out-more-stuff