Sullivan has written of himself often as a conservative in the tradition of Edmund Burke and Michael Oakeshott, who (with apologies to Corey Robin) are known in the popular telling as standard bearers for a kind of conservatism of skepticism. This skepticism is not a skepticism in the sense of a narrow materialism or aggressive atheism. It is instead a skepticism towards people and institutions, towards both their goodness and their capability. It's a kind of conservatism that leads one, for example, to oppose welfare programs not out of a rejection of their purported ends but out of doubt that these programs can reliably reach those ends, or that they can do so without destructive unintended consequences. Sullivan's conservatism, I have always understood, is predicated on the notion that even fundamentally good people are corruptible and fallible and that the road to hell is paved with good intentions. This, to me, is the message of The Conservative Soul.
This commitment, outlined in a book published in 2007, has been severely challenged by the events of 2008. The presidency of Barack Obama has changed Sullivan's politics and his writing, by my estimation. His support for Obama is neither unconditional nor free from criticism. But it is considerable, and defined by a deep belief that Obama is playing both a political and policy "long game." In this telling, any apparent failure, scandal, or bad decision of the Obama administration can be understood as merely one part of a master plan that will lead to victory, both political and moral. (Sullivan recently wrote about his desire to find a better cartoon character to represent Obama's political advantage over the Republicans; Sullivan has repeatedly used the Roadrunner's dominance of Wile E. Coyote as an allegory for Obama's mastery of the GOP.) Sullivan's regard for Obama has also involved an iconography that has been, at times, somewhat disconcerting for someone of my temperament.
As I've said, there is no fair accusation that Sullivan has shielded Obama from proper criticism. As someone who argues with the truly zealous Obama defenders on a daily basis, he cannot be accused of the kind of unhinged hero-worship that has grown among some partisan Democrats. Yet I still find myself disturbed and confused by this transformation. If you asked me to define one trait that would be least reconcilable with the conservatism espoused in The Conservative Soul, it would be deference to a particular leader. I cannot square the recognition that all political leadership is subject to corruption and failure with the kind of faith Sullivan regularly shows in Obama. And this becomes a deeper confusion when you see how this trust has filtered down from Obama to the people and programs beneath him.
This faith in the goodness and constraint of a particular government has reached, I hope, it's zenith in Sullivan's yawning response to a vast system of government surveillance that must involve thousands of people with disparate agendas and different characters. Here, more than ever, I would think a conservatism of skepticism, which recognizes the ample possibility for human failure, would create great suspicion and criticism. Even if you have far more faith in Obama's goodness than I do, even if you think that goodness is represented in his senior advisors, you have to recognize the vast potential for abuse in a system like this. The history of powerful human systems is a history of their corruption. All it takes is a small group of people working within such a program, one which by design lacks accountability and external review, for this kind of information be used to silence dissent, to pursue personal vendettas, or to unfairly harm without due process. This country should know very well the destructive power of functionaries and bureaucrats when they are armed with power and a lack of accountability
Just today, Sullivan wrote this:
the tradition I have long studied and thought about is not a conservatism finding solutions to problems. It is about finding solutions to problems you suspect may not be solutions at all, and may be moot once you’ve done your best; it’s about the elusive nature of prudential judgment; the creation of character through culture; the love of what is and what is one’s own; and a non-rational grasp of the times any statesman lives through. It is about a view of the whole that keeps politics in its place. It is, in the end, a way of being contingently in the world.How can these beliefs possibly be reconciled? How can a man who admits the elusive nature of prudential judgment trust the judgments of thousands of totally unaccountable government functionaries? How can he believe that a system bent on total secrecy and total denial of oversight or restraint would represent a culture that could instill character? How could he look at this vast, dehumanized and dehumanizing surveillance system and not see a potentially failed solution to a problem that is, in perspective, a fact of life in the modern world? I cannot reconcile the philosophy with the individual commitments. I no longer really know how to read Andrew, at this point.
Perhaps this is a consequence of 9/11, and the way that the one-time destructive power of a small group of disparate lunatics challenged the American psyche, in a way that has caused many people to lose any notion of proportion or of rational threat estimation. Or more simply, maybe I've simply been misreading Sullivan's discussion of his own politics. Whatever the case, I would like for Sullivan to consider the possibility that he is placing far too much faith in a bureaucratic apparatus that contains a multitude of agendas and all of the potentially for mismanagement and bad behavior that engenders... a scary thought, when that apparatus is connected to military power. These programs are run by people, and people are fallible and frequently immoral. (It's worth noting that many of the people working in these programs are the same people who worked under the Bush administration that Sullivan has rightfully criticized.) It would take so little for all of this to go wrong.
I don't expect anyone to have a fully articulable or consistent political philosophy. I don't. My politics are filled with weird tensions and paradoxes and contradictions. I just wish that someone who has spent so much time trying to articulate his political philosophy would take a step back and consider how that commitment fits with his affection for a particular leader, and perhaps, rediscover some of his skepticism.