Yesterday on MSNBC, Lawrence O'Donnell took Rush Limbaugh to task for suggesting on his radio show that Jesus would not be happy with raising taxes on the wealthy, or using any of those funds for social welfare. Good stuff.
The most frequent response to Lawrence's argument (that Jesus commanded that we give up everything and help those less fortunate than ourselves) is that Jesus would have wanted us to be charitable in a more direct and personal manner, rather than having the government act as a middle man.
Both viewpoints are, of course, speculative at best. I don't think that Jesus would have imagined in his wildest dreams (and he was God, for Chrissakes) that societies would have grown to resemble anything like we have in developed countries today. I also don't imagine that Jesus would have known that so many of his followers would be covetous douchebags.