The underlying issue is the dilution rate of the dollar. From 1998 to 2008 the money supply was diluting at ~10% a year. With the money supply growing that fast, and CD's are paying only ~3% a year, holding anything other than dollars seems like a good idea. So people speculate in stocks, gold, oil, real estate - anything that dilutes at a lower rate than dollars. But most people aren't good at speculating, so they lose money.
No government running a sound money system should be diluting at 10% a year. It's simply inexcusable.
Since the expectation (integral of probability density times outcome) of such games can be net-negative, he might be. It depends on how prevalent those games are.
There's another angle, too. What matters for the economy as a whole is not one player's expected outcome, but the sum of the expected outcomes over all the players.
http://fora.tv/2008/10/21/Richard_Kovacevich_Evolution_of_th...