Why Chief Justice Roberts’s Tax Ruling Makes Life Incredibly Awkward for Both Obama and Romney

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By ruling yesterday that Obamacare's mandate is constitutional only as a tax, and not as an exercise of Congress's power to regulate the economy, Chief Justice John Roberts walked a tightrope between both liberals and conservatives, pleasing both in different ways. Liberals get to keep their precious Obamacare, and conservatives get to delude themselves into thinking that Roberts has given them a long-term victory by neutering the reach of the federal government going forward. But Roberts's tax argument also had the effect of making the topic of Obamacare really, really awkward for both Barack Obama and Mitt Romney.

The obvious problem for Obama is that the GOP can now (has already begun to) justifiably accuse him of imposing a new tax on millions of Americans. Even worse for Obama, he's on video claiming, repeatedly, that it is not a tax. Taxes + deceit = Not a good look! And if Obama decides to continue insisting that it's not a tax, despite Roberts's opinion, then he delegitimizes the very Supreme Court decision which upheld Obamacare. In short, he's screwed if Roberts is right, and he's screwed if Roberts is wrong.

But for Romney to make an issue out of Obamacare's taxes, it would place him in just as uncomfortable a situation. One of the many similarities between Obamacare and Romneycare is that they both enforce their mandates by penalizing — sorry, taxing — people who fail to purchase health insurance. So Romney can criticize Obama for the tax if he wants, but only if he wants to bring attention to Romneycare's own penalties taxes and be called out as the most hypocritical hypocrite in the world.

Considering the pitfalls awaiting both Romney and Obama, both White House hopefuls might be smart to avoid the topic of Obamacare altogether. We doubt they will — after all, it sure fires up the troops. But during the debates, for example, where a cutting rebuttal could become a devastating soundbite, this seems like dangerous territory. At a minimum, Roberts has increased the, uh, penalty for trying to score points on Obamacare.