Just a little background: pragmatism is America's only home grown prominent philosophical movement. It was formulated by the likes of Charles Peirce, John Dewey, C. I. Lewis, Sidney Hook, and others, including the most radical member of the team, the recently deceased Richard Rorty. In America's community of jurists, several major pragmatists stand out, including Oliver Wendell Holmes, Jr. and, today, Richard Posner and Cass Sunstein.
From knowing that these people are pragmatists it isn't a simple matter to tell what kind of political philosophy and public policies they champion. Indeed, with a pragmatist you can never tell. That is why it is such an alluring general philosophy – no one can hold you responsible for anything since a cardinal feature of pragmatism is the rejection of all principles. This is ironic, since among major countries America is the one most clearly associated with a set of principles, as identified in the Declaration of Independence and the Bill of Rights of the U. S. Constitution. For the country, then, to have developed the pragmatic approach to law and public policy is a tragic contradiction. All of the fundamental ideals and principles that America is known for is rejected by pragmatism and pragmatists. They take them to be myths or, as one major contemporary pragmatist recently emailed me, as pure BS!
So what is afoot here? Throughout human intellectual, including political history the great contributors have mostly attempted to find basic principles of justice and good community life on which to rest the institutions of society. The very idea of the rule of law rests on principles that aren't mere personal preferences, arbitrary intuitions, wishes, hunches and such but something stable so citizens can tell in the main (though not in detail) what to expect and what will be unacceptable. To want this is to want a coherent enough philosophy of community life but for skeptics it amounts to wishing for the impossible, some kind of ideology that has no firm relationship with reality. Pragmatists have concluded that such an aim is hopeless – no basic principles are available at all, as far as they see it. So what is left? Well, nothing much outside one's personal hunches, preferences, desires, wishes and such. None of this, according to them, is true or right but at best widely shared. But that, too, isn't a requirement in pragmatic thinking. Whatever works, is the motto of the pragmatist – a phrase that was recently used by Woody Allen as the title of a movie in which he seriously promoted the idea.
Problem is, sadly, that "whatever works" is hopelessly vague. When something works, it does so because it helps promote a valuable goal. Exercise works if it makes one fit, diet works if one manages to lose a few pounds, the engineering strategy of lowering a massive box on to the gushing oil in the Gulf of Mexico works if it manages to contain the flow. So what is left unaddressed by "whatever works" is what a policy is supposed to work for and why that instead of something else.
After all, corruption works for those who want to garner illicit gains! Lying works for those who want to deceive, etc., etc. Which simply says that depending on what one aims for, anything might work. There is no check on any policy this way, nothing that renders it successful or not. Whatever works is a blank check, a ticket with which any kind of conduct may be excused however vicious, harmful, fruitless it turns out to be, since anything can work for some purpose and if no standard (principle!) can be identified for distinguishing sound from unsound purposes, then whatever works is just an empty gesture, a wave of the hand, toward the real thing, namely a solid standard of right and wrong.
Any political candidate who proclaims proudly that he or she is a pragmatist must, therefore, be watched very carefully because the pragmatist ploy is, ultimately, a ticket to unchecked power, a world in which trickery, muscle, and such are the arbiters of acceptable policies, never mind whether the rights of citizens are being crushed in the process.