Icing on the Cake

How Cynthia Hyndman won before the highest court in the land

Published in 2022 Illinois Super Lawyers magazine

By Taylor Kuether on January 28, 2022

Cynthia Hyndman didn’t expect to argue in front of the U.S. Supreme Court. In fact, the case she ended up arguing—CBOCS West, Inc. v. Humphries—crossed her desk largely by chance. 

“It came into our office through a former partner of ours. She’d had the contact with our client, Hedrick Humphries,” Hyndman says. 

Humphries was fired from his mid-level management position at a Cracker Barrel for speaking out against the alleged race-based firing of a Black coworker. Humphries sued for retaliation, originally filing under Title VII of the Civil Rights Act of 1964 and Section 1981 of the Civil Rights Act of 1866.

Hyndman’s team took the case on a contingency basis, losing at the district court in a summary judgment. They appealed, got the judgment reversed, and the case was poised to go back to the district court for trial when the defendant decided to file a petition for writ of certiorari with the U.S. Supreme Court.

“At the time, I had never filed or dealt with a cert petition,” Hyndman says. But she and her team enlisted the help of Carolyn Shapiro, professor of law at Chicago-Kent School of Law and a former clerk to Justice Stephen Breyer. “There was no split in the circuits; in fact, it was unanimous among the circuit in favor of our petition. She said there just isn’t anything here; they’re not going to be interested and you don’t need to respond unless they ask you for a response,” Hyndman recalls. “Next thing you know, we get this notice from the court that they’d like a response to the petition. So we put together our response—Carolyn helped us with that—and we filed it.”

Then, in late September 2007, the phone rang. “Our receptionist buzzed me and said, ‘You’ve got a call from the Supreme Court.’ I pick up the call and they’re like, ‘We just want to let you know the court granted cert in your case today,’” Hyndman says. “So then we’re in total panic mode. We have a case going to the Supreme Court; now what do we do?” 

Hyndman went to her partners first. “We had the case on a contingent basis, we weren’t getting paid, it was going to take up our time from other hourly billing work. I probably spent 95 percent of my time on that case,” Hyndman says. “To their credit, they said, ‘No, this is a once-in-a-lifetime opportunity, do it.’ So we jumped in.” 

The prep was a whole different world. “All of the sudden, you have everyone interested in a case you’re working on,” she says. The legal question was whether or not there was cause of action for retaliation under the Civil Rights Act of 1866. “Because it was a civil rights issue, there were lots of people who were willing to help.” 

That included five moot courts: Northwestern, Harvard, Stanford, Georgetown and Public Citizen. “It was really helpful to have people firing questions at me and getting used to the kinds of questions I’d be asked at the court,” Hyndman says. 

They also petitioned the Solicitor General’s Office to file an amicus brief on their behalf. “It was immensely helpful and ultimately may have even really tipped it for us. It was kind of a bold move, considering it was the second Bush administration, and to think they would come weigh in on civil rights in employment was kind of cheeky, but we thought there was a good chance that they would and, in fact, they did,” she says. “They sent us an email: ‘If we file on your behalf, will you cede 10 minutes of your argument time to us?’ And I thought, ‘You can have the whole damn thing if you come in on our side. Take as much time as you want!’ So they did, which was huge.”

On the day of the argument, in February 2008, the client, several firm colleagues, and Hyndman’s entire family—about 20 people in all—were there. “I felt like I had this entourage,” she says.

The room was smaller than she thought it would be. “You go into the courtroom and you’re right up by the bench. They’re so close that if you’re standing at the podium, you can’t see all nine justices—they’re out of your peripheral vision, that’s how close you are.”

The first question came from Justice Antonin Scalia, whom she recalls cracked a joke at her expense. “I didn’t get any questions from Thomas, which was not unusual. Did not get any questions from Souter. Alito asked a few, and I got a real softball from Ginsburg, which was great. One from Breyer, some from Stevens. Roberts and Kennedy might have been the two that asked me the most questions. I couldn’t really get a sense of where Kennedy was going. Roberts was very interested in the stare decisis issues that were raised,” Hyndman remembers.

“Justice Breyer tends to ask really long questions that are sometimes hard to get to the bottom of, but [co-director of Stanford’s Supreme Court Institute] Pam Karlan gave me a great piece of advice: She said, if you get a question from Justice Breyer or Justice Ginsburg, the answer’s yes. Just don’t even mess it up. Don’t even think about it, just say, ‘Yes, Justice Breyer; yes, Justice Ginsburg’ and move on. They’re going to be completely on your side and they’re not going to ask you anything to trip you up.”

The whole experience was over fast. “You just sort of have this out-of-body experience. It’s pretty remarkable. I felt really good about the argument—really positive,” she says. “I flew back that night and, on the plane, I was reading press about the case and everyone was saying it doesn’t look good, they think we’re gonna lose, and I’m thinking, ‘Wait a minute, were we at the same argument? I thought it went really well!’”

All that was left to do was wait. At the end of May, another call came from SCOTUS. “We ended up winning 7 to 2 in a case people thought we were going to lose,” Hyndman says. “Arguing it was exciting, but winning it was really fun. I’m a litigator; I really like to win. It was the icing on the cake.” 

So was the call to her client. “It meant we had the green light to go back and have a trial,” she says. 

Ultimately, the case settled in mediation. “It was a great, cool experience, but it had real-life consequences for a real-life person, so that made it even more exciting to go all the way up to the Supreme Court to help a guy who really deserved to be helped.”