This paper takes a closer look at the trilogy of Harper, Little Sisters, and Sharpe. On the one hand, it laments the Court's lack of commitment to the expressive freedom, both as individual judges and as an institution. It may be a fresh century, but the opportunity for a fresh start under section 2(b) may already have been lost. On the other hand, though, the dissenting opinions in Harper and Little Sisters are encouraging. In addition, the Court should be given credit for granting expressive freedom some protection in Little Sisters and Sharpe. The qualification, however, is that in each case its support for the guarantee was seconded to strategic considerations. Specifically, the Court sought to minimize the institutional consequences of protecting expressive freedom by declining to invalidate the impugned legislative provisions. To the extent section 2(b) gained ground in these decisions, the question is whether principle was sacrificed in the process.