I don't necessarily think Jesus was a libertarian, or a liberal. We don't really know what his politics would have been, if he did indeed have any views at all. Jesus' focus was on personal behavior the kingdom of God, salvation, that sort of thing, not politics.
That said, I find it silly when liberal pundits say that since Jesus hung out with sinners, said to pay taxes, and healed sick people that he supported high taxes UHC and welfare or whatever absurd concoctions that liberals will come up with. Jesus didn't say "Government do this" he said "You do this."
I refuse to use the government to steal in order to help the poor. That is MY position. Whether Jesus would agree with me or not I guess I'll find out in heaven. But I don't think Jesus is going to judge me based on my political views so much as what I, personally, do for his kingdom. Politics were just not Jesus' concern.