Someone once asked how I would feel about voting for a gangster. My answer was this question cannot be answered out of context. What if all the candidates are gangsters and there are no other choices? What is the current form of government - will their power be somewhat limited by checks and balances, and what are the major issues, if any, on which they will be voting? Are they in charge of the dog catchers or the U.S. armed forces? Will they be tasked with making appointments to other federal agencies or are they just sitting on a limited city council? What if the political position does give the power to regulate the market, and Gangster X is known to take money from a free market group while Gangster Y takes money from communists and the only major issue during their term is regulating the market? What if the position is that of a figurehead, and Gangster X is a Don Corleone-ish family man who really cares about the future of the community (despite the hypocrisy) and projects a positive and benevolent spirit, while Gangster Y is a psychopathic nihilist who projects disdain and contempt for human life? How long is the appointment - is it a one year position or a lifetime appointment? If, for example, this position carries an enormous amount of power and is a lifetime appointment, a la Chavez or Castro, then we should be talking about armed rebellion - not voting!
In other words, the full context must be taken into consideration when voting. That context involves myriad factors and can require a fairly detailed understanding of the various factors involved as it relates to your own self-interest, including the history of the candidates, recent political history, the nature of the current government, the major issues at stake, the term of the appointment, and so on.
It would be a grave mistake to simply declare, "Gangster X is a gangster," then proceed to dissect the implicit philosophy of an abstract conceptual gangster (irrational, dishonest, violent, etc.) and subsequently deduce that any decisions emanating from a particular gangster (because all gangsters are irrational, dishonest, violent, etc.) must be bad. This latter approach is a textbook case of rationalism. It represents an attempt to obtain knowledge through deduction from concepts in your head rather than from facts. On the other hand, dismissing this larger context, and concluding, without qualification, that Gangster X is an all-around great guy that is impervious to error, just because you heard him give a nice speech or observed him doing a few good things, would also be an error - albeit, an instance of empiricism.
Let's go back to the example where the only choice is Gangster X or Y. Let's throw in that X is known to be a womanizer while Y lives in a basement and rarely interacts with people outside his caporegimes. Also, X is overtly religious and wants to appease Muslims due to his mushy Christian altruism, but he hates communism. Y is an atheist who takes a stand against Muslim terrorism - although a lot of that actually emanates from his psychotic love of death and war. Say the position is a two year position, and there will be many votes pertaining mostly to regulating the economy including health care, the Internet, and the energy industry - but they will have little power over anything else including foreign policy and our relations to Islamic radicals. Gangster X takes money from a free market PAC while Gangster Y takes money from George Soros. Gangster X has said he believes in a mostly free market approach while Gangster Y wants a full government takeover. Also, X's son and nephew head an energy concern and hate environmentalists.
Now, does Gangster X really believe in free markets? Probably not - he is just taking money from free market people who tell him what to say, he hates communism but for non-objective religious reasons, and he wants to benefit his relatives. Is he a good guy? No - he spent his life as a womanizing criminal despite his somewhat hypocritical public posture. Is he a religious fanatic? Yes, but it is not that relevant to how he is likely to vote on the issues before him and he has no other power to impose his religion on others given his limited power and the other branches. Could he be bought by the socialists if they pay him more? Maybe, but we know for sure that Y is already taking money from socialists. Also, we may hate X's tendency to appease terrorists, but he will have little or nothing to do with those policies, so who cares? Finally, given the nature of the two year term, it is likely there will be better candidates, but if Y gets a foothold, and given the nature of statism and the current political framework, he can use his regulatory power to further his ambitions by shaking down industries to enhance his power and fill his campaign war chest while spreading corruption. If this is all we know, we have a better shot of freedom enhancing outcomes with Gangster X, over the next two years, given this context.
Would it serve our interests to just surrender to Gangster Y and his followers, who are also bad people but vote against us every time? Isn't it likely that once entrenched, Gangster Y and his socialist followers, with growing power over regulating the economy while shaking down businessmen, could wreak havoc on the economy for many years to come? Even if you want to make an argument, that letting Gangster Y win will somehow serve your interests in the long run - for example, maybe you argue that the carnage from his statist policies will expose socialism as a horrible system (as if we didn't know) - you still would need to take into account this full context. You cannot simply rule either out because they are a gangster or because they are a religious fanatic.
If you want to advocate a position, you need to integrate political philosophy with political facts. We would love to have a bunch of George Washington's, who are principled in both theory and action, overseeing a constitutionally limited republic, and we should advocate the principles that hopefully will result in more George Washington's in the long run, but even if this were possible, you always have to advocate for politicians within a context. Washington was wrong about many things too, as were the other Founding Fathers.
In general, we should never judge a candidate in a moral vacuum as if we are judging his candidacy for heaven. Ayn Rand, in her essay, How to Judge a Political Candidate, said:
One cannot expect, nor is it necessary, to agree with a candidate’s total philosophy — only with his political philosophy (and only in terms of essentials). It is not a Philosopher-King that we are electing, but an executive for a specific, delimited job. It is only political consistency that we can demand of him; if he advocates the right political principles for the wrong metaphysical reasons, the contradiction is his problem, not ours. [emphasis mine]With respect to a presidential election, I would submit the following as a partial list of relevant factors to consider: What will the likely issues be over his term? Is the economy collapsing, are there serious foreign threats emerging, is political correctness threatening civil liberties? Will there be multiple supreme court vacancies? Since an executive is different than an intellectual, does he have the temperament to be a leader in a fast moving high stakes environment? Will he pick good people to advise him and will he listen and communicate effectively with subordinates? What is his history? Who does he take money from? Where are his real interests financially? Does he need money or already rich? Who are his close advisers? Who is he likely to bring into the administration to head cabinet agencies? What types of people will he put on the supreme court or in the federal judiciary? What kind of people will he pick to head the military and intelligence services which speaks to both foreign policy and civil liberties. Who are his relatives and close friends? Who helped him in politics? Is he a cheerleader for good ideas even if he doesn't or can't implement them (like Reagan was)? Does he have a good spirit when advocating for America overseas, i..e, what message does he send to the world about America and American interests? Does he provoke fear in our enemies or does he project weakness and appeasement (like Obama did)?
As a great example, recall Ayn Rand's consideration of the Nixon candidacy (The Ayn Rand Letter, “The American Spirit,” page 136). Despite Nixon's flaws (which could be analyzed out-of-context), she weighed the importance of his supreme court picks which would outlive his presidency - a totally rational and pertinent factor:
We may hope that Nixon might gain time for the nation, by granting some relief (i.e., removing a few chains) to the private sector of the economy and by arresting the growth of the public sector. But, in view of his record, we cannot be certain. There is, however, one promise of his 1968 campaign – perhaps, the most important one – which he has kept: the appointment to the Supreme Court of men who respect the Constitution. It is still too early to tell the exact nature of these men’s views and the direction they will choose to take. But if they live up to their enormous responsibility, we may forgive Mr. Nixon a great many of his defaults: the Supreme Court is the last remnant of a philosophical influence in this country.
In closing, I will add that an integrated approach to a significant election requires knowing a lot about politics (political facts) and political philosophy. Books and essays are written about political figures, giving inside accounts that speak to temperament, their past political affiliations, recent political history and many of the factors cited above. Given this complexity, even following a rational, integrated method is difficult and fraught with the potential for honest errors and mistakes - while open to debate among reasonable people. However, engaging in purely rationalistic or empirical arm-chair arguments for politicians is a much bigger and more insidious problem that should be understood and avoided.