I've read Com. v. Sebelius, and what struck me on the first reading was that Judge Hudson seemed to say that if the Congress and the Administration had characterized the individual insurance mandate as a revenue measure from the get-go, the outcome might have been different. "In concluding that Congress did not intend to exercise its powers of taxation under the General Welfare Clause, the Court's analysis begins with the emphatic denials by the Executive and Legislative branches that [the penalty for not buying health insurance] was a tax," Judge Hudson wrote.
In other words, by hedging on the extent to which the penalty for failure to buy health insurance was an outright money grab by the United States, the proponents of the scheme forfeited a potential basis for upholding its constitutionality.
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