“The first time I was taught about Obamacare, it was explained to me by Stuart Butler at the Heritage Foundation in the mid-90s,” conservative blogger Andrew Sullivan said in conversation with Jeff Greenfield at the 92Y this past spring. “It’s this great free market idea to bring healthcare to the uninsured, and it was where the Right was really headed. It is a right-wing idea promoted by an essentially small-c conservative president.” 
It’s a well-worn cliche in liberal circles that the individual health insurance mandate now manifested in Obamacare had its roots not in the radical or even progressive tradition, but in the conservative one. It was first developed by the Heritage Foundation in 1989. It was the health care plan signed into law by Mitt Romney during his governorship of Massachusetts. The earliest incidence of united Republican opposition to the individual mandate seems to have occurred in 2009, when President Obama began pushing for the Patient Protection and Affordable Care Act. This led many to view the Republican party as no longer being guided by any particular philosophy or ideology, but as a reactionary front to the Obamafication of American politics and society.
Indeed, so swift an about-face on the healthcare mandate only seems plausible if one views the modern Republican Party as a contra-Obama party rather than a conservative one. From a conservative point of view, there may be several aspects of Obamacare that are worthy of reform—such as various price controls—but in its essence, the Affordable Care Act is the universal healthcare plan most faithful to traditional American ideals.
However, that doesn’t answer the question of whether a self-proclaimed libertarian should support the compulsory purchase of health insurance. And I doubt that I’ll be able to answer that question in a single blog, since “libertarian” is an umbrella term that includes a wide range of political and economic philosophies. Someone who rejects the very premise of the state, or who only accepts a state that strictly adheres to the non-aggression principle, is not likely to support the mandated purchase of anything, even something as societally beneficial as health insurance. But a libertarian more broadly defined—someone who holds conservative views on the economy and liberal views on social policy—should be seen as a plausible object of persuasion.
In 2012, Hayek scholar Erik Angner wrote a piece for Politico on this very subject. While acknowledging Friedrich Hayek’s disapproval of mandates, Angner notes the Austrian economist’s support for redistribution in the form of a guaranteed minimum income. He further states that the mandate, which he describes as “only a minor deviation from the Hayekian ideal” is also more “politically palatable” than direct cash transfers. The piece became the subject of an interview of Angner by Reason’s Nick Gillespie, which also touched on economist and libertarian icon Milton Friedman’s support for redistribution schemes including the negative income tax and the voucher system.
I have often been labelled by other libertarians as a “left-libertarian” due to my cautious yet adamant support for Obamacare along with other redistribution schemes that rely on market solutions to social welfare problems. However, I reject the label, since “the left” has historically denoted the struggle for egalitarianism, which I see as an ignoble and miserably failed project. I strive not for equality, but securities that allow people to take risks, be entrepreneurial, and move between socioeconomic strata within their own lifetime. In 2012, an incumbent who sought to bring those securities to the American public defeated a candidate who allowed his own state to enjoy them, but disowned them when it became politically necessary. I wasn’t old enough to vote then, and although I didn’t feel the same way at the time, in retrospect I’m glad that election turned out the way it did.
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