you could always go the Donald Sterling route
invest in land, redline minorities get sued and settle and still make dough
buy an NBA team, try to move it once illegally, then move it, pay the minimum salary cap possible for years in clear tanking efforts, bang smuts the entire time and get caught saying wild shit
forced to sell your team
investment: 12M in 1981 or whatever
sold for 2.1B a few years ago, even w/ the obvious divorce settlement that's one of the greatest investments of all time
what's really crazy is had Donald Trump's USFL team actually been successful, that same story could have been him instead hahahaha