Can we even fit him into one of those molds?   

Good question Michelle

Would he be a combination of them? 

OK ok, I won't give a short answer this time. The tough part about it is that the Achille's heel of any economic system is the same all across the board, and Jesus was surely aware of this: human beings. So long as there are corrupt individuals, there will be problems in economics. On paper, communism sounds great: a classless, stateless system where every individual is given exactly as many goods and services as s/he needs. In reality, we had the Soviet Union. Corrupt gov't officials remained rich, while the working class was dirt poor, having to wait on heavily rationed commodities, and since they knew they'd get the same pay no matter how much they worked, there was little incentive to work hard.

Capitalism works better, I think, in part because it assumes people will be selfish. So long as the market is free and supply/demand is left to work it's magic, and there is active competition everything works great. The government would step in where it needs to (laws against monopolies; see Standard Oil), and otherwise let things go as they will. Problem is, we have a (very) corrupt government that's looking after the interests of the large corporations, instead of the common good of society; e.g. giving GM--a company that was doing badly BEFORE the recession--big bucks so that they can keep running their crappy company poorly(sounds like communism there, actually...), rewarding bankers who screwed over our economy by being greedy instead of having passed laws to prevent it from happening in the first place, etc. Meanwhile passing laws that interfere with normal supply and demand in ways that are unhealthy for the economy, such as paying farmers not to grow food to artificially raise food prices, etc. (I'm leaving out some because I don't want to spur an off-topic debate).

Socialism's main goal is to have as many people as possible (preferably everyone) involved in economic decisions. The way most of our elections go, and the most common intelligence level of Americans, I think it's a very bad idea. However, ideally, if everyone was educated and researched their decisions before voting, it could work well. I also like the idea of mixed capitalist/socialist economy where business are generally free to do as they see fit, but with some kind of fences set up so they don't wander into stupid territory, such as subprime loans.

tl;dr version, I have no idea which system Jesus would support. I think he would want a system where everyone was treated fairly and had opportunity to voice their opinions, but at the same time, he would know that people are corrupt, and very bad things can happen if any one group or set of groups (think the circle of evil of healthcare: doctors, insurance, pharmaceuticals) have too much power.

Really, I think that the ideal situation would be for society to follow the examples seen in Acts, where all are committed to helping those who are less fortunate themselves in the best way they can be helped (i.e. not necessarily throwing money at them). But, that was a small subset of Roman society, and such a subculture hasn't existed since then (to my knowledge).

My thoughts exactly. I think, and I'm just guessing here at the moment, is that with the forming and formalization of the Catholic Church and their need to be seen as the mediators between God and man, and the large amounts of corruption that was there, is that the common people got to seeing that taking care of the less fortunate is The Church's Problem and that so long as they gave to the Church, they were doing their part. The collapse of the Roman society, and the ensuing dark ages might have to do with it as well, since there were no longer large cities where people lived closely, but were more spread out, and pretty much everyone was dirt poor. *shrug*

My thoughts are going that way as well, as far as how much he would really care about the economic system. Just based on the fact that he never said much about the economy, but encouraged giving to the less fortunate and helping those in need. Maybe in an ideal world it wouldn't matter so much because if everyone just plain cared about their fellow man, most people's needs would be met.

I think Jesus was leaning toward more of a socialistic viewpoint. As Paul noted it is our greed that gets in the way and as long as we remain fallible and corruptible greed will continue to be a major stumbling block. I think until He changes us from corruptible to incorruptible we will continue to have this problem. Every one of us has been greedy at one time or another.

Because Christ followers are human, and humans are selfish.

I thought we already answered that one :]

Good luck with that.