Does anything in particular about 'the meek shall inherit the earth' strike you as an aspect of a religion that appeals to winners?
My essay isn't about whether you like Christianity or not. And I think it can be demonstrated using objective terms that anyone would agree to regardless of faith, that the Christian world is VASTLY more successful by virtually any measure than the Islamic world. A man on the moon and a bone in the nose are not the same thing.
So a better question I think, is why would one assume that simply being meek makes one a loser?
In the western (read Christian) world, faith and success are not mutually exclusive by any means.