I saw this article in the LA Times about measuring Olympic Medals per capita. I like the idea, but I also think figuring in the GDP of the country makes sense. The US could throw a lot of money at an individual event and probably fair pretty well.
I got the GDP via Wikipedia and used the CIA column because it had the least NAs in it. North Korea isn’t on that list, so I added it manually from here.. Then I got the medal count from Yahoo (I mean Yahoo!).
So Zimbabwe with its $151 of GDP per person wins 4 medals. They did the most with the least, so far.