I think this is a great topic and it's understandable that people who love Jesus would ponder this at election time.
I have gotten some interesting insights when considering this question of how Jesus would vote. In the first place, I don't think Jesus would ever allow his political position to be known. Jesus fully understood his own power. One of the greatest powers of all is the power of influence. Knowing that humans would take the easy path of having Jesus make all of their decisions for them without thinking these things through for themselves, I think he would keep his political opinions to himself. I'm not suggesting that most of us should do that, but I think that the Pope, for instance, should keep his politics to himself. Religious leaders should never endorse political candidates; this whole election has really driven home for me the wisdom of the separation of church and state.
Clearly, Jesus calls us to learn how to think—not what to think. When we all become adept at independent cosmic thinking we will naturally come to more Godlike conclusions and be able to make more Godlike decisions. That is, decisions which create the greatest amount of good for the greatest amount of people for the greatest amount of time.
We know from his life and teachings that Jesus deliberately avoided making pronouncements on political issues. The closest he came was "Render unto Caesar the things that are Caesar's and unto God the things that are God's." We could write a novel on what he meant by that. But suffice to say, it doesn't give us much to go on at election time. However, I think we can look at his life by example and infer some definite qualities to look for in a leader. Here are some things I have thought of:
These scientific, moral, and spiritual insights, these cosmic responses, are innate in the cosmic mind, which endows all will creatures. The experience of living never fails to develop these three cosmic intuitions; they are constitutive in the self-consciousness of reflective thinking. But it is sad to record that so few persons on Urantia take delight in cultivating these qualities of courageous and independent cosmic thinking. The Urantia Book, (16:6.9)
He was honest and sincere. He said what he meant and meant what he said. He spoke the truth even when the truth hurt. He was loyal to the highest principals in the highest sense of the word. He would be righteously indignant of the false and malicious political spin and negativity that we have become accustomed to.
He was courageous. He was willing to put himself on the line even to the point of direct contradiction with the powerful religious rulers of his day.
He was fair. He never would have thought only of the interest of his people (the Jews) or his nation (Israel). There was no self-interest in him. Everything he did was for the greatest good for all. From my point of view, the most powerful man in the world should also be a good world citizen. A true leader would want to lead mankind, not just America, into a new and better way of life. As Jesus said,
He was wise. He understood human nature well enough to know how certain people would react in certain situations.
"When you once begin to find God in your soul, presently you will begin to discover him in other men's souls and eventually in all the creatures and creations of a mighty universe. But what chance does the Father have to appear as a God of supreme loyalties and divine ideals in the souls of men who give little or no time to the thoughtful contemplation of such eternal realities?" (155:6.13)
He was patient. He waited for the right time to act and chose his battles and his opportunities very carefully.
He was respectful and trusting. He believed in men because he knew that God is in them. He empowered men to decide and act and supported the wisdom of the group. When the group made a decision he honored it.
He was merciful. He understood the human condition and was forgiving of human frailty. However, he abhorred deliberate wickedness, he said that more was expected of the Master than of the servant, and in the end he did not tolerate the corruption of false leaders.
He was sympathetic. He had real insight into the human heart and the human condition. He had real compassion for humanity and wanted all people to "have life and have it more abundantly."
He was truly kind. I don't think he would ever have resorted to harming anyone or allowing anyone to be harmed. He once said that he would not defend himself against harm unless he discerned that God was not present in the person who sought to harm him.
Clearly, we can't expect a leader, even one with as much power as a US president, to possess all the wonderful qualities that Jesus did. There were many powerful men in Jesus day that had no respect for Jesus and thought him foolish and weak. There are many powerful people today, even those who profess to follow Jesus, who would never endorse his non resistant and non violent ways. Many who think that, although Jesus ideals are truly good, they're not practical and they won't work.
Sadly, at this point in time, we are stuck with the reality of always having to choose between the "lesser of two evils." That is, two mortal men who are anything but perfect. We can take the easy way out and vote along party lines, trusting that at least our basic political philosophies will be upheld, or we can look at each man and try to discern their true character.