Jay Cost argues that liberal legal analysts were blind to conservative arguments against Obamacare:
The problem for the left is that they do not have a lot of interaction with conservatives, whose intellects are often disparaged, ideas are openly mocked, and intentions regularly questioned. Conservative ideas rarely make it onto the pages of most middle- and high-brow publications of news and opinion the left frequents. So, liberals regularly find themselves surprised when their ideas face pushback.
Of course, conservative legal analysts also underestimated the Supreme Court's willingness to entertain certain arguments. Ilya Somin, who authored an amicus legal brief against Obamacare's individual mandate, said in the video above, from a few weeks ago, that the odds were against opponents of Obamacare. Allahpundit, who thinks Cost makes some fair points, nevertheless counters:
Even I was surprised at how hostile the conservatives on the Court seemed to be towards the mandate. That’s not because I’m reading back issues of The Nation, it’s because the painful fact remains that the Supremes almost always let Congress do any ol’ thing it wants when it comes to regulating commerce.
How Chait defends liberal legal analysts:
[T]he shock of the liberal analysts who expected a landslide does prove they misjudged the case, but their error lies not in underestimating the arguments, which they imbibed closely, but in overestimating the Republican justices.
The Dish 