Often the first question the lawyers Ted Olson and David Boies get when they talk about their effort to overturn California’s anti-gay Proposition 8 is this: Are there five votes on the Supreme Court for their case? Olson, a Republican (and former U.S. Solicitor General), and Boies, a Democrat, are the dream team who led opposing legal camps in Bush v. Gore when that case was before the Court, in 2000, deciding the election for President Bush by a vote of 5-4.

After the customary and cautionary language about never being able to predict the Supreme Court’s result, Olson and Boies often answer the question by going a step further. They say that they are not giving up on any of the Justices. Boies then tells a joke—he says that he and Olson have a deal: Olson will be responsible for getting the votes he got in Bush v. Gore, and Boies will be responsible for the ones he got. Everybody laughs. (One example is here.) So does the Supreme Court’s health-care ruling make the joke more or less funny for conservatives?

There are two big gay-rights cases heading for the Court. (I’ve posted about them.) In addition to the Olson-Boies Proposition 8 case, there is the Massachusetts case known as Gill v. Office of Personnel Management, which challenges the constitutionality of the federal Defense of Marriage Act (DOMA). A petition for certiorari review was filed in Gill on June 29th by the conservative lawyer Paul Clement, representing Republicans in the House of Representatives, who are prosecuting the case for DOMA, since the Obama Administration declined to defend it. In an unusual procedural move late last Tuesday afternoon, the Justice Department also asked the Court to consider the Gill case and another DOMA case, Golinski v. O.P.M., even before it was decided by the Ninth Circuit. The Court will certainly take the Marriage Act case and decide it during its next term. But I also think they will not resist the temptation to take the Proposition 8 case, even though they may later agree to handle it narrowly.

The Court will not have much flexibility in the DOMA cases. There is only one question presented: Is DOMA constitutional? It will have to be answered yes or no. In the Proposition 8 case, there are more options. The Court might restore same-sex marriage rights in California without finding a nationwide constitutionally based right to marriage equality. Even some advocates think that would be the best and most politically sustainable result. But there is little doubt that if the Court rules in favor of gay rights the decision will be significant, perhaps even historic. Most people assume that the fifth and deciding vote belongs to Justice Anthony Kennedy, who wrote the Court’s majority opinions in its two most recent big gay-rights rulings, Romer v. Evans (1996) and Lawrence v. Texas (2003).

Chief Justice John Roberts joined the Court in 2005, two years after Lawrence was decided, after only a short stint on the D.C. Circuit Court of Appeals. None of the gay-rights-related cases that have come before him as a judge give any significant clues as to how he might rule on the weighty constitutional issues he will face next term. Interestingly, as the Los Angeles Times reported in 2005, before he was on the bench he “worked behind the scenes for gay rights activists” in the Romer case who were represented at the time by his law firm, Hogan and Hartson.

But now, in these marquee gay-rights cases facing the Court next term—as American public opinion, especially among young people, shifts rapidly towards greater equality—Roberts may find the very kind of “legacy” issues around which he has shown a willingness to break with his more conservatives colleagues. Put another way, these cases will help define what freedom and equality look like in America, perhaps for decades. Will Roberts want to be on the losing side of history?

Olson, writing in Time about the health-care ruling, says the “decision abounds with legal and political ironies.” Although he goes on to discuss this incongruity in a different context, he has been hypothesizing for some time that the influences on Chief Justice Roberts in the health-care case might also lead him to rule in favor of the rights of gay Americans to full equality, including marriage. There is some reason to believe that Roberts would not want to be seen as leading a Court of right-wing judicial activists.

Fundamentally, we see that Roberts thinks of himself not just as another Justice of the Court but as its Chief Justice and, as such, as the primary keeper of its legacy. He is fifty-seven, and could serve on the Court for another twenty years or more. In the context of public opinion on gay rights and same-sex marriage, twenty years is a very long time.

If they decide against the rights of gay people next term, within a decade or so this issue is going to be right back before the Court and Justice Roberts will likely still be Chief. For example, it took seventeen years for the “wrongly decided” gay-sodomy issue (Bowers v. Hardwick, in 1986) to come back to the Justices and be overruled in the Lawrence case. It would likely happen more quickly now. At only the current rate of increase in the polls (about 1.5 per cent a year according to some estimates), that could put equal rights for gays, including marriage, at about a sixty-five per cent or higher approval rating.

If he rules against gay rights now, how is Roberts going to feel about the overturning of this precedent later—or having it overturned while he is still on the Court as Chief? That’s not to say public opinion is the only factor here. But the Supreme Court has previously held that marriage is a fundamental right, and sexual orientation, especially when viewed from today’s perspective, meets all the requirements for heightened constitutional scrutiny. It is because of the persuasiveness of those main arguments that we even get to the issue of public opinion. Historically, it is in these situations that public opinion matters and can be significant, as it was with the Court’s rulings on civil-rights issues. It’s never an issue of the Court looking to public opinion for the result—but they do look to the direction the country is headed, and at its normative values, to see if the result will be accepted by the governed. This is the gay-rights moment, just as the sixties was the civil-rights moment (although there are places, like the South, where public opinion is contrary, as it was in those landmark civil-rights cases).

Some theorize that Roberts tried to depoliticize the Court with his health-care ruling in order to gain some credibility before even more conservative decisions to come, like overturning affirmative action. Anything is possible, but that is not likely to be the outcome in these gay-rights cases, where Justice Kennedy will probably not be with conservatives. The question is whether a decade or more from now Chief Justice Roberts really wants to be leading a Court that embodies the last vestiges of anti-gay discrimination in the country, even as fewer and fewer Americans oppose equality. A ruling in favor of gay equality is possible, perhaps even likely, with or without the swing vote of Justice Kennedy. After the health-care decision, Ted Olson’s belief that he can get John Roberts’s vote for same-sex marriage is no joke.

Photograph by Charles Dharapak/AP Photo.