The end of a Monopoly game can be quite awkward. A player eventually will go bankrupt, and according to the official rules, he must "turn over all that he has of value and retire from the game."
It has been my experience that if a person goes bankrupt in life, he typically does not retire from everything. That logic affected me, my family and friends when growing up, and whenever someone went bankrupt in a Monopoly game, that person became a "Monopoly hobo" and continued the game as a street person.
Monopoly is fun and all, but having the hobo added an element that increased the fun level tenfold. We often had conversations like this:
Property holder: You owe me $800 for staying in my hotel.
Hobo: I only have $6.
Property holder: Six bucks! Are you kidding me? My hotel costs $800.
Hobo: Please, sir, have mercy. Do you want my six bucks?
Property holder: Whatever. You should be ashamed of yourself!Typically, the hobo would hope to land on free parking, AKA win the lotto. Officially, putting money in the free-parking spot is not in the Monopoly rules, but the game would probably be unbearably boring without that quirk.
Upon further review, arguably the most I have ever learned about humanity came from Monopoly. How we treated the hobo probably showed a lot about ourselves. Strangely, I think I enjoyed being the hobo more than hoisting up hotels on St. James Place.