Robert Yablon, a senior associate in Orrick, Herrington & Sutcliffe’s Supreme Court and appellate practice was a little hard to reach on Friday. "Sorry," he said when The Am Law Daily finally caught up with him. "I’ve been really busy."

For good reason. The 35-year-old Yablon was preparing for something that is unusual among law firm associates: an appearance before the U.S. Supreme Court on Monday morning at which he is scheduled to make oral arguments in United States v. Davila.

"It’s obviously quite rare to have an associate do an argument, particularly a person at a private firm," says Jeffrey Fisher, the codirector of Stanford Law School’s Supreme Court Litigation Clinic who himself argued before the Supreme Court at age 33. It’s an especially impressive accomplishment, Fisher adds, given the emphasis law firms with Supreme Court practices have come to place on those groups as a way of luring both clients and potential hires.

Shortly after the Supreme Court agreed to hear U.S. v. Davila on January 4, Joshua Rosenkranz, head of Orrick’s Supreme Court and appellate litigation practice, told Yablon that he had been chosen to argue the case. Yablon, a Green Bay, Wisconsin, native, has been preparing for the hearing ever since with moot courts and by reading relevant cases. "I’m excited about this opportunity, and I appreciate working at a firm and in a practice group where these opportunities are shared," he says.

Yablon, a Rhodes Scholar, has the credentials to support Rosenkranz’s faith in him. After graduating from Yale Law School in 2006, he clerked for Judge William Fletcher of the U.S. Court of Appeals for the Ninth Circuit before completing back-to-back Supreme Court clerkships with, first, Justice Ruth Ginsburg and, then, Justice Sonia Sotomayor. He joined Orrick in November 2010.

In his return to the court, Yablon will face questions from his former bosses and the seven other justices in a case that turns on whether any degree of judicial participation in plea negotiations automatically vacates a defendant’s guilty plea regardless of whether the judge’s involvement prejudiced the defendant.

Orrick’s client, Anthony Davila, pleaded guilty in 2010 to one of the 34 counts on which he had been indicted for allegedly defrauding the government out of $423,500 through fraudulent tax refund claims. Davila’s guilty plea followed a hearing during which a magistrate judge presiding over the case told him that pleading guilty could reduce his punishment. In December 2011, the Eleventh Circuit vacated the conviction after determining that a judge’s participation in plea negotiations, even if he or she intends to help the defendant, creates a risk that a guilty plea may seem coerced and jeopardizes the judge’s impartiality.

The government appealed the ruling, arguing that the appeals court should have considered whether the judge’s participation prejudiced Davila’s plea.

Yablon began working on the case last fall, shortly after Orrick—which is handling the matter pro bono—was brought on as appellate counsel.

"Rob is a brilliant lawyer. Truth is, there’s no controversy about it at all at our firm, though I’m sure there are raised eyebrows in the bar at large," Rosenkranz says of the decision to have Yablon handle the oral arguments. "Rob will be ready. He’s been through the wringer."

As Yablon approaches the biggest event in his young career, nerves will no doubt be a factor. At the same time, he says he hopes the 100 Supreme Court hearings he observed while serving as a clerk will help put him at ease: "For me, that courtroom is a familiar place."

Plus, eight months ago, he completed what could be considered a warm-up for Monday’s arguments: His wedding to Miriam Seifter, a visiting researcher at Georgetown Law Center whom Yablon met while clerking for Justice Ginsburg. The justice officiated the wedding.

"That’s the only thing I can think of that compares," he says. "I was afraid I’d forget the vows I’d written and tried to memorize in advance."

And how did he fare on that occasion?

"I did a pretty good job."