Liberty and equality (the equal guarantee of positive outcomes) are do not go hand in hand. The fact is that every attempt society has made to “level” the playing field, they have brought down those at the top while leaving those at the bottom still at the bottom. This fact becomes quite clear after studying history and getting a basic understanding of human nature. People will first attempt to find an equality among all under the guise of freedom.  This is the attempt to elevate those at the bottom without infringing on rights of them or those above them.  This, however almost never works. Because the call for equality is so strong, society will eventually give up liberties and chose to live in “equality in slavery”.  He claims that people will rather live in a society of total poverty and anguish than feel as though others have unfairly (regardless if they actually achieve ‘unfairly’ or ‘legitimately’) achieved while others have unfairly failed.
While it is clearly my opinion that we should always choose liberty over equality (I find myself in good company with the founding fathers), I want, at the very least, to educate people who equality will always come at a cost.  You may decide that cost is worth the return, but don’t ever assume that equality is free.