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As Sandy Levinson's posts (including the most recent) have suggested, when we think about the current administration and the Supreme Court, our thoughts almost inevitably turn to the mid-1930s. It's easy to push the parallels between the Roosevelt and Obama administrations too hard, but some parallelism does seem to be there: taking office mid-crisis, offering ambitious policy proposals with some prospect of success in Congress, and -- importantly here -- facing a Supreme Court staffed by justices whose ideological formations (or "judicial philosophies," if you like) contain important elements that could be used to put into constitutional peril some aspects of the administration's policy proposals. (Here too we shouldn't exaggerate. The Court in the mid-1930s endorsed an expansive, Hamiltonian interpretation of the general welfare clause, thereby putting its stamp of constitutional approval on the Roosevelt administration's Keynesian spending programs. The full story is, as they always are, even more complicated.)
The pivotal actor at the Supreme Court during the constitutional confrontations in the mid-1930s was Justice Owen Roberts. Early in the Roosevelt administration Justice Roberts generally cast his votes with the Court's judicial conservatives. During the 1936 Term he cast his votes with its liberals. After that he reverted to form, as an important recent paper shows. In 1936 Justice Roberts faced and made a choice. It would be nice if we could preserve the parallelism by saying that in the 2010s (Chief) Justice Roberts will have to face and make some choices. More likely, though less symmetrical, Justice Kennedy will be in the first Justice Roberts' position.
(Pop quiz: List the justices who shared a last name -- Harlan, Jackson, Marshall, White, Roberts, ???)