The Key to Keynes

Quick thought: Is there a "critical mass" for capitalism, ie. will there always be a loser?
Is there a maximum amount of capital out there in the world that, by the very nature that it is limited, prevent some ("third world", the "South", or "undeveloped" countries) from ever achieving economic parity with the "developed" world?

During my reading for my humanitarian aid class, it struck me that the base assumption of development aid policy is that the Western industrialized countries can "develop" the undeveloped countries to a point of self-sufficiency. Does our market capital system have room for that? Can there be no "bottom", or -- to put it harsher -- "losers"? Can everybody win?

I think the simple answer is "no". But the more complicated and ethical answer is that the "bottom" can come up only if the "top" comes down a little bit, and we would all occupy various strata of the "middle".

A collegue of mine countered that instead of meeting in the middle, basically the entire strata of rich to poor would be shifted upwards. So, the bottom comes up, but the top also goes up.
That doesn't make sense to me. That means that more "Stuff" (capital, money, resources, etc.) must exist, because more of it is going to the bottom and more of it is going to the top. Can that happen?

(I'm sure Econ 101 could have answered this for me. Damned Organic Chemistry got in the way in college.)