Four reasons the White House is likely to lose the Halbig case before the Supreme Court

3. I assume Chief Justice Roberts is with the original four dissenters from Sebelius two years ago in opposing the administration. This gives him the chance to atone for his error in upholding Obamacare as a valid use of the taxing clause in that case. His decision in Sebelius did great violence to the Constitution’s protections for federalism — it will be the mission of his Chief Justiceship to repair the damage. Plus, the insincere misreading of the statute will grate especially hard on Roberts’s professionalism — he seems to take seriously getting the right lawyerly answer to technical statutory questions. Justice Kennedy, who is usually the swing vote, was strongly in the dissent against Obamacare two years ago, and I cannot see him engaging in legal gymnastics to save a law he thinks is already unconstitutional. 

4. The Court will be acting in agreement with, rather than against, majority wishes. The last election gives the court political cover to cut back on Obamacare. Given the election results, a majority of Americans support repeal or radical restructuring of Obamacare. If the Court rules against Obama here, it will be acting with the support of a majority of Congress. What judge can resist the chance to reach the right legal result, fix mistakes from the past, and act with popular support?  It’s a Supreme Court trifecta.