Tomorrow, conservative legal giant Ted Olson will begin a new trial, this one involving a federal challenge to Proposition 8, California’s ban on same-sex marriage. The case, Perry v. Schwarzenegger, is the latest and arguably most important legal review of what has become a nationwide debate about affording rights to same-sex couples.

That the New Jersey Senate on Thursday rejected legislation to legalize same-sex marriage a month after New York’s state Legislature did the same only heightens the stakes for Prop 8 opponents. So significant is the case that U.S. District Judge Vaughn Walker ordered that the proceedings be broadcast on delay via YouTube – a significant measure given that federal courts bar television cameras.

Such high-profile legal tussles are nothing new for Olson, who has argued 55 cases before the U.S. Supreme Court, including his representation of then-Gov. George W. Bush in Bush v. Gore, the case that sent Bush to the White House. Olson would later serve that administration as solicitor general.

Before that, he was an assistant attorney general for President Ronald Reagan’s Office of Legal Counsel. He’s a longtime fixture in the Federalist Society, the epicenter of conservative legal thought. All of which makes the side Olson has chosen in the California case – he’ll argue that state-imposed bans on same-sex marriages violate the Constitution – surprising to many. As does the fact that Olson’s cocounsel is David Boies, who represented the former vice president in Bush v. Gore.

Read the rest of Michael Smerconish’s column in The Philadelphia Inquirer here.