A similar scene took place last fall, when the D.C. Court of Appeals took up the case. As news outlets reported at the time, Judge Laurence Silberman -- a Reagan appointee who was elevated by President George W. Bush -- was among those hammering the administration's lawyer with questions about the individual mandate and the limits of power.
Forbes declared, "D.C. Appeals Court Points the Way to the Defeat of Obamacare's Individual Mandate." Conservatives then sounded triumphant too.
The American Constitution Society reported at the time:
Silberman appeared dissatisfied with DOJ attorney Brinkmann's efforts to meet their request for a "limiting principle" putting judicially enforceable boundaries around Congress' commerce power. In addition, [the judges] noted that the fact that Congress had never enacted a provision quite like the ACA mandate might be an appropriate basis for judges to set aside the presumption of constitutionality normally to be accorded to laws passed by Congress.
Randy Barnett, an architect of the "Obamacare" challenge, also chimed in:
The low point for the government was when Judges Kavanaugh and Silberman pressed counsel for about 10 minutes for a single example of any economic mandate that would be unconstitutional under the government's theory of constitutionality. To their evident frustration, she refused to provide any such example.
Less than two months later, Silberman cast the deciding vote to uphold "Obamacare."
In his majority opinion, Silberman located the "limiting principle" he was looking for on his own, and knocked down the heart of the conservative argument. The judge declared that not buying health insurance was hardly an economic "inactivity" because the uninsured directly impact the system regardless.
Silberman's blow to the GOP in that case is particularly noteworthy because he's not known for being friendly to Democrats. In 2004, journalist Michelle Goldberg charged that Silberman "has often behaved as if his paramount role as a federal judge is to protect Republicans, persecute Democrats and slander anyone who disagrees."
On Tuesday, Kennedy and Roberts aggressively questioned an at-times stumbling U.S. Solicitor General Donald Verrilli about the breadth of federal power if the mandate is allowed to stand. Later they expressed some sympathy with the argument Silberman made about the uniqueness of the health care market.
It's too early to know where the justices will come down -- the Supreme Court might yet strike down "Obamacare." But Silberman's initial skepticism should serve as a cautionary tale: Conservatives' confidence -- and liberals' gloom -- may be premature.