The outcomes in free speech cases—like the one Washington Attorney General Rob McKenna is arguing before the U.S. Supreme Court tomorrow—are notoriously hard to predict.

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“When you come to these free speech hearings, conservative and liberal are not always easy to discern,” says Arthur Hellman, professor of law at the University of Pittsburgh and a Supreme Court expert. “Free speech is a funny kind of thing that way—the players sometimes switch positions. The conservatives are on the free speech interest one day, and on the other side the next.”

The contemporary court has recently provided two examples that highlight this tendency, and they're worth looking at in the lead-up to tomorrow's oral arguments over whether releasing the names of those who signed petitions to put R-71 on Washington State's ballot last year amounts to some sort of free speech violation.

Last year the District Court of Northern California tried to provide a live video feed of the courtroom challenge to Proposition 8, the 2008 initiative that banned same sex marriage in that state. After supporters of the ban complained of extensive harassment and expressed fear that a live feed would only lead to more harassment, the Supreme Court torpedoed the planned video feed by a vote of 5-to-4, with the five right-leaning justices lining up against the four left-leaners (although the reasons the majority gave for the stoppage were procedural, they were strongly influenced by the charges of harassment).

But McKenna points to a different case to support his prediction that the Supreme Court will ultimately decide initiative signatures are a matter of public record, and that releasing them is not a free speech violation—even if those signatures are related to a controversial gay rights measure, as they were in the case of R-71, which unsuccessfully sought to roll back domestic partnership rights in Washington.

During the infamous Citizens United case, in which the court upended decades of tradition and granted corporations the same speech rights as people, the justices also voted eight-to-one to uphold the precedent that corporate expenditures and campaign contributions are subject to public disclosure. McKenna thinks that same instinct toward making the political process transparent should bring the court to his side in this case.

However, even though it makes good legal sense, there are reasons to doubt that McKenna's strategy will win the day. If the justices end up ruling along common left-right lines, and if Kennedy ends up siding with the conservative bloc as he did in the ruling on the California video feed, then McKenna's toast—as is the Washington Open Records Act. (Kennedy is a well-known swinger, so this is a realistic possibility. He often sides with the right wing of the court, and on top of that he was the one who Protect Marriage Washington turned to in their attempt to appeal to the Supremes.)

“Everyone,” Hellman says, “will be listening very carefully to Justice Kennedy, because he will very likely be the deciding vote."

I'll be among those listening from inside the Supreme Court hearing room, and will let you know what I hear from Kennedy and all the rest tomorrow. As for a final decision: The Supreme Court is unlikely to reach one until the beginning of summer.