When Northwestern Pritzker School of Law professor Sarah O’Rourke Schrup appeared before the U.S. Supreme Court last October for oral argument, she cemented her place in court history.

As the opening case on the docket at the start of the session, Schrup was the first lead counsel to take advantage of the court’s new “two-minute rule,” implemented in a change to the court’s Guide for Counsel. Schrup’s team represented James Kahler in Kahler v. Kansas.

It was also the first time Schrup argued before the Supreme Court. Schrup and Sidley Austin partner Jeffrey T. Green supervised a group of Northwestern law students through the Bluhm Legal Clinic’s Appellate Advocacy Center.

Schrup is a member of a relatively small group of women who have received the chance to appear before the nation’s top justices. Over the last decade the percentage of women arguing before the Supreme Court has ranged from 12% to 21% per term, according to SCOTUSblog.

In December, the American Constitution Society’s Chicago chapter hosted a panel discussion, which included a group of Illinois women attorneys who have argued before the nation’s highest court, to discuss why there are so few women given the opportunity and what can be done to close the gap.

The Daily Law Bulletin followed up with a few of the panelists to discuss their experiences being among the few women who get the chance to argue before the U.S. Supreme Court.

These interviews have been edited for length and clarity.

Sarah O’Rourke Schrup

Sarah Schrup

Case:Kahler v. Kansas, No. 18–6135

Argued: October 2019

Result: In a 6-3 decision, the high court ruled Kansas’ decision to abolish the insanity defense does not violate the Eighth or 14th Amendments.

Then & now: Professor, Northwestern Pritzker School of Law; founder and director, Appellate Advocacy Center

CDLB: What was the most memorable experience you can recall when you appeared before SCOTUS?

Schrup: I argued the first case of the term and it was the first case where the Court had instituted the new rules about two minutes of uninterrupted argument. To be the first advocate to use these rules and to have two minutes where I could make my case to the Justices, in a way that no one was able to do for the last 25 years, was definitely memorable.

CDLB: What did you learn about yourself through the experience?

Schrup: I didn’t know how I would feel the morning of and whether nerves would get the better of me. Many consider this the pinnacle of one’s legal career; would the pressure and the import of the moment impact my ability to argue the case? It didn’t.

CDLB: How did your past legal experience prepare you?

Schrup: I’ve been doing appeals for 20 years — taking the lead on close to 100 cases — and I’ve been running the appellate clinics at Northwestern for roughly 15 years. I have argued in the 7th Circuit, the Illinois Supreme Court and the Illinois Appellate Courts and I’ve taught students how to do this. Teaching students makes you break it down a little bit differently than if you were just blindly forging ahead in your own case. Those processes that I use with my students are tried and true, and I used them myself in this case.

CDLB: What advice would you give to women lawyers who are interested in arguing before the Supreme Court?

Schrup: This is an important topic to me because there are so many amazing women lawyers that it just boggles my mind why we don’t have more representation in appellate courts and specifically the Supreme Court. Though it is true that women haven’t historically argued much in the Supreme Court, but that was a byproduct of having few women lawyers. But now almost 50% of law school graduates are women, and the numbers should not look as they do. I think women need to keep their eye on the ball, be proactive about getting appellate opportunities — especially pro bono and government work — and be vocal about what they can and want to do.

CDLB: How do you think the legal field has changed for women since you started practicing? What changes still need to be made?

Schrup: There was basically no appellate specialty when I started out. There were a few lawyers in a few law firms mostly in Washington, D.C. That has definitely changed, and I think it is due to the near-celebrity status of the Supreme Court, the emergence of Supreme Court Clinics in law schools and SCOTUSblog. For women, it could go both ways. Increased visibility in the field might create more transparency and more opportunities. But Supreme Court practice has become a lot more competitive, and the court is taking almost half the cases it took 30 years ago. If there are fewer spots, it is likely that those will go to the long-term institutional players, which overwhelmingly have been men.

Lisa M. Madigan

Lisa Madigan

Case:Illinois v. Caballes, No. 03-923

Argued: November 2004

Result: In a 6-2 decision, the high court found a criminal defendant’s Fourth Amendment rights were not violated when a state trooper used a drug detection dog during a traffic stop and it did not unreasonably prolong the incident.

Then: Illinois Attorney General

Now: Partner, Kirkland & Ellis LLP

While serving as Illinois attorney general, Madigan argued her first and only case before the U.S. Supreme Court in November 2004, Illinois v. Caballes. During Madigan’s 16-year tenure as AG, her office argued nine cases before the nation’s highest court. Today, she’s a partner at Kirkland & Ellis LLP.

CDLB: What was the most memorable experience you can recall when you appeared before SCOTUS?

Madigan: You don’t want to go before the court and get asked a question you don’t have an answer to. So I spent a couple of days with [the] Illinois State Police dog trainer. I learned how the drug-detection dogs function, because I knew there’d be a question about it. In fact, I read a whole book about the history of dogs in law enforcement to prepare for the question. I thought the question would come from Scalia, who always asked historical questions. Well, I didn’t get the question. It turns out [then-assistant U.S. attorney general] Chris Wray got the question, and it came from Justice Stevens. I wanted to jump out of my chair and answer the question because I had spent days preparing for it.

Also the Supreme Court puts out a guide for counsel in cases to be argued before the court. My recollection is it warns you not to attempt humor, because it usually falls flat.

For people who haven’t argued or watched an argument in front of the court, they may not realize that some of the back-and-forth between the bench and counsel is lighthearted.

There was a moment where Justice Stevens, who was presiding, asked a question about the defendant getting pulled over going just 6 mph over the speed limit in Illinois. Justice Stevens said, “Well you know I think I’ve been known to drive over that limit in Illinois.”

I made some comment to the effect of, “Well it’s always nice to have you in the state of Illinois, Justice Stevens.”

Luckily, instead of falling completely flat, I got a few smiles and laughs. I broke the rule, but it worked out alright.

CDLB: What did you learn about yourself through the experience?

Madigan: It’s another example of the fact that women lawyers can do anything. I was eight months pregnant when I argued. When you get to the court the morning of your argument, counsel arguing go to the lawyers’ lounge. I was there with my Solicitor General at the time, Gary Feinerman.

Christopher Wray was there with Michael Dreeben from the Justice Department. Opposing counsel was there. Because I was pregnant, I needed to eat.

While we were waiting to go into the courtroom, I was eating an apple, and apparently the lawyers from the Justice Department pulled my solicitor over and said, “What is she doing? We’ve never seen anybody eat before an argument.”

It’s a long way of saying: You do what you need to do. You prepare; you learn your case; you learn the record; you learn all of the cases that are relevant to your case; you delve in to the facts. So when you have this relatively unique opportunity to argue in front of the nation’s highest court, you are ready to do well.

CDLB: What advice would you give to women lawyers who are interested in arguing before the Supreme Court?

Madigan: If you want to argue before the U.S. Supreme Court, you are going to need to work very hard and you’re going to have to advocate for yourself. That means you’re going to have to take as many opportunities as possible to argue in front of appellate courts, but you are also going to have to step up and say, “I want to argue this case.”

Maybe it’s a case that you argued in the lower courts. Maybe it’s a case where you know all of the facts. When there is an opportunity to argue in the front of the U.S. Supreme Court, you have to be prepared to argue the case and you have to be prepared to make the case for why you would be the best person to argue it. No one is going to give away that opportunity.

I certainly saw it, not with me, but with my opposing counsel. There were plenty of people who called him up “offering” to argue the case. He wouldn’t let it go, and women have to be the same way.

CDLB: How did your past legal experience prepare you?

Madigan: Preparing to argue before the U.S. Supreme Court reminded me a lot of law school in the sense that I had a voluminous number of cases to read, and you have a series of moot courts in preparation. The other thing that I thought prepared me very well were the numerous press conferences I had, where I got used to being asked questions and having to respond on my feet. I think that is invaluable experience, and it’s similar to what most lawyers get when arguing in front of an appellate court.

CDLB: How do you think the legal field has changed for women since you started practicing? What changes still need to be made?

Madigan: I’ve been a lawyer for 25, almost 26 years at this point. And there are many more women lawyers in leadership positions. You see more women partners, many more general counsels, and judges. Plus, look at Chicago, Cook County, and the state of Illinois, you see more women lawyers in political leadership.

As more women have gone through law school they have used their degrees as a credential to take on increasing amounts of responsibility and leadership.

I think there’s still an enormous amount of room for improvement whether you are looking at private practice or government. For top leadership positions, there are certainly plenty of women lawyers who are qualified, and they need to keep on pursuing them.

They also need men and women to support them so they can take on those roles and responsibilities.

Carolyn J. Shapiro

Carolyn J. Shapiro

Case:Duncan v. Owens, No. 14-1516

Argued: January 2016

Result: The court dismissed the case, which addressed habeas relief, as improvidently granted.

Then: Illinois solicitor general

Now: Founder and co-director of IIT Chicago-Kent College of Law’s Institute on the Supreme Court of the United States

Carolyn Shapiro, founder and co-director of IIT Chicago-Kent College of Law’s Institute on the Supreme Court of the United States, argued Duncan v. Owens before the U.S. Supreme Court in January 2016 while serving as the state’s solicitor general.

CDLB: What was the most memorable experience you can recall when you appeared before SCOTUS?

Shapiro: It’s a pretty awesome experience, in the literal sense of the term.

I did have this funny moment: Elena Kagan was my law professor, and the first day of the first class I had with her at law school, she called on me by name before the seating chart had gone around and I was very surprised — I didn’t know she knew who I was, and I sort of looked around like “Is she talking to me?”

[During the argument] I was answering Justice Sotomayor’s question and then, all of a sudden from the other end of the bench, I hear, “Excuse me Ms. Shapiro” and I did have this flashback to law school when she called on me for the first time in law school.

I also spent a very large amount of time before the argument working on what I was going to say first with the other lawyers on my team — we worked hard on that. So getting that out felt really good.

It’s good that they make you say, “Mr. Chief Justice and may it please the court,” because words come out of your mouth, you realize that you’re not going to fall over, and then I said my opening line and immediately Justice Sotomayor asked me some questions.

CDLB: What did you learn about yourself through the experience?

Shapiro: I know that I really like working as a team and I had some really outstanding lawyers who I worked with and it would have been a much more challenging experience had I not had that. That really made an enormous, enormous difference.

You think of it as being a solo experience when you watch or listen to somebody argue but in my experience of it, I’ve been a team member as well as the person arguing, it really is a team effort. It’s just a colossal amount of work to be ready for anything which is what you have to do for a Supreme Court argument and it is a team effort.

CDLB: How did your past legal experience prepare you?

Shapiro: I had clerked on the Supreme Court so I had seen many arguments, including some by the best oral advocates out there include John Roberts. I had done a number of other arguments in appellate courts, including the Illinois Supreme Court and the 7th Circuit.

I think it would be very challenging to do an oral argument in the Supreme Court without having ever done an oral argument before, although people do it. Elena Kagan, for example, when she was solicitor general her very first oral argument was in front of the U.S. Supreme Court.

Of course the fact that I was a law professor for a long time before I argued and I focus on the court in my academic work, so I have a lot of different perspectives about what’s going on in the court.

CDLB: What advice would you give to women lawyers who are interested in arguing before the Supreme Court?

Shapiro: The evidence appears to show that women are much more likely to argue in front of the Supreme Court when they work for government offices. If you look at the relatively small number of women who are arguing, I believe the majority of them are attorneys’ general or the solicitor general of the United States or public defenders. That definitely is one avenue and I think it has a lot to do with client relationships in private practice.

If a person is interested in getting their through private practice I think it’s crucially important to know that the senior partners you are working with see that as a part of their mission to bring up younger lawyers and give them those unique opportunities.

I think there are some that are pretty clearly dedicated to that and those would be the opportunities I would want to seek out.

CDLB: How do you think the legal field has changed for women since you started practicing? What changes still need to be made?

Shapiro: I do think thatthe advent of the ability to work remotely has been incredibly value because it gives people a lot more flexibility. And while that should matter to both men and women, I think it is as a practical matter particularly valuable for women with young children.

At the Supreme Court level, there’s definitely been a tightening up of this Supreme Court bar that does an extraordinarily high percentage of the oral arguments and I think that’s both good and bad. It probably elevates the briefing and the arguments to some degree but I think it’s unfortunate because it cuts down on those opportunities for other people. And I don’t think you have to be a Supreme Court specialist to do well in the Supreme Court. I think you have to be a good lawyer and appellate experience is incredibly important but there are very good lawyers who argue in the Supreme Court who have not spent their careers doing only that.

The practice of law can be pretty brutal in the sense that it can kind of be all consuming. I think that’s unfortunate for everybody. I think there’s an increasing sense from everybody about the importance of balance and mindfulness and I hope that is something that the legal profession is taking to heart.

Anita M. Alvarez

Anita Alvarez

Case:Williams v. Illinois, No. 10-8505

Argued: December 2011

Result: In a 5-4 decision, the high court held the defendant’s Sixth Amendment right to confrontation was not violated when he was unable to question lab technicians at his trial.

Then: Cook County State’s Attorney

Now: Managing director at Alvarez Marsal Disputes & Investigation

Former Cook County state’s attorney Anita M. Alvarez, now the managing director at Alvarez Marsal Disputes & Investigation, argued Sandy Williams v. Illinois, in December 2011 while serving as the county’s top prosecutor.

CDLB: What was the most memorable experience you can recall when you appeared before SCOTUS?

Alvarez: The whole process is memorable. Just going into that courtroom is majestic, everything about it is absolutely beautiful.

What was memorable to me was just getting up there and being able to do it. I was nervous. It doesn’t matter how many trials I’ve done, it’s a whole different experience. There’s a whole procedure where you have to look at the chief judge and say, “Mr. Chief Justice may it please the court,” and then you start your argument. Well that’s all I got out of my mouth before the questions started. Sotomayor asked me the first question and then it was rapid-fire question after question.

Everything that I prepared, I had my bullet points nicely written, that all kind of went out the window when I had to answer all of the questions. I remember clutching the podium with my hands and once the questions stopped I was able to go back to my original plan and get those bullet points out. Most of them came out in the context of the answers but I was able to go back and do them in the order which I prepared.

They also give you a quill, that’s kind of your parting gift for everyone who argues. Well I got two of them which was pretty neat too.

CDLB: What did you learn about yourself through the experience?

Alvarez: I used to tease my supervisor from the appellate division and his crew that was prepping me that, “You appellate lawyers use a different part of your brain” because as a trial lawyer you are so used to being in control of your case. You know what your argument is, you prepare it, nobody stops you mid-sentence and even if you get an objection it doesn’t break your flow.

When you do an appellate court argument it’s a whole different ballgame. You’re really kind of not in control because it’s all about theory and hypos and it’s almost as if every justice plays devil’s advocate. Like I said all I got out of my mouth was may it please the court and then the questions start. They’re not necessarily regurgitating what your facts are they are giving you hypos.

It was a pivot for me to at that point in my career to say “OK now I am going to do this appellate court argument but it’s not just an appellate court argument it’s the Supreme Court of the United States.” I argued that in December of that year and I had just gotten off trial. I had done a double jury that started in September.

CDLB: How did your past legal experience prepare you?

Alvarez: One thing about being a trial attorney is you are used to being on your feet. You’re used to having to think critically and having to switch gears say the judge rules against you on whatever the issue might be. You can’t stand there, sit down and pout you have to regroup and figure out what to do next. The more experience you have as a lawyer and you’re used to those kind of stressful situations, be it a trial or an appellate court argument, you’re more suited to do it.

CDLB: What advice would you give to women lawyers who are interested in arguing before the Supreme Court?

Alvarez: I would love to see more women appear before the United States Supreme Court. I think you have to go for it. You have to be aggressive in saying I can do this, I’m prepared, I’m experienced enough and I want to do this argument. You have to speak up for yourself, be vocal about it because Supreme Court arguments are rare.

I think you have to speak up for yourself, I think we as women always have to do that and kind of remind our colleagues that we’re just as experienced as they are and we can do this. We have to be advocates for ourselves in order to make sure that we’re able to get an opportunity like that.

CDLB: How do you think the legal field has changed for women since you started practicing? What changes still need to be made?

Alvarez: When I started way back when at least in the state’s attorney’s office it was mostly men. In my first couple of years in the office really my partners were men but when I left the office was 54% women. So little by little you can see the profession change and more and more women are choosing to go into law.

Just what from my involvement with the Chicago Bar Association and the Women’s Bar Association of Illinois, it seems that at that managing partner level we’re still lacking. I would hope little by little we’re going to see women in those roles, I would think we should be there already but it still looks like we may still be lacking.

Cindy H. Hyndman

Cindy Hyndman

Case:CBOCS West Inc. v. Humphries, No. 06-1431

Argued: February 2008

Result: In a 7-2 decision, the high court determined a worker can sue his employer for retaliation under the Civil Rights Act of 1866.

Then and now: Shareholder at Robinson Curley P.C.

Cindy H. Hyndman, a shareholder at Robinson Curley P.C., in February 2008 argued CBOCS West, Inc. v. Humphries, on behalf of Hedrick Humphries.

CDLB: What was the most memorable experience you can recall when you appeared before SCOTUS?

Hyndman: I do remember having this feeling during the argument standing there, sort of an out of body experience where I looked around and thought, “Wow I’m arguing before the Supreme Court” and it was just kind of surreal almost.

The first question I got was from Scalia, that was a little scary, especially because I representing a plaintiff in a civil rights case and he was not particularly friendly to my position.

CDLB: What did you learn about yourself through the experience?

Hyndman: I learned that I was capable of doing more than I thought I could do. It was daunting, it was a little scary. The cert petition was granted about a week after my mother died and I was in a particularly vulnerable position and wasn’t sure if I was up to the task. I had a lot of people calling me and telling me that I had to turn the case over to them but my law partners were adamant that I should do it and it was really challenging. It was the most challenging thing that I’ve done.

In some ways it was a new skill I learned that I could do it and I could do it well. It really sort of challenged me professionally and intellectually in a way that I hadn’t been challenged before.

CDLB: How did your past legal experience prepare you?

Hyndman: I had argued in the 7th Circuit and I had argued in some appeals courts. I knew that I could dig into a case and learn everything I needed to learn about it, I could analyze the issues do so efficiently and get to the bottom of the questions that needed to be answered.

CDLB: What advice would you give to women lawyers who are interested in arguing before the Supreme Court?

Hyndman: Be very, very, very, very prepared. You just can’t underestimate the preparation that you need to have. You’ve got to know everything there is to know. Seek help from people that have done it before and there is a whole universe of practitioners, people that have specifically have supreme court bar practices. The law schools that have supreme court institutes are very helpful I’ve found. Reach out to anybody you know that’s argued the case in the Supreme Court or has clerked for a Supreme Court justice.

I had a few outliers of people who just wanted to take the case and run with it but for the most part I found a community of people who were incredibly supportive and really helpful.

CDLB: How do you think the legal field has changed for women since you started practicing? What changes still need to be made?

Hyndman: I think for women there are a lot more opportunities. You’re starting to see women in positions they weren’t in when I started practicing in 1982. Happily there are a lot more women judges, a lot more women high up in firms and general counsel. That’s encouraging, but it’s not nearly where it needs to be.

There are still shockingly situations where I go to court and opposing counsel will be there with a male partner and the male partner does all the talking and doesn’t even let the woman attorney introduce themselves. There’s still bastions of misogyny that are kind of mind boggling, but I think that it’s starting to get better.

I feel like I get the respect I deserve and that wasn’t always the case as a young woman attorney. Though I still feel really underestimated at times, and that’s fine with me.

Women just need to be given the opportunities, in law firms especially, to be given cases and to run with cases.

Ellen Robinson, who was the founding shareholder of our firm, used to say that she believed that women litigators were much better than men because we were very prepared because we had to be. When you go into court you have to know everything and you need to be very prepared and because of that we have an advantage. Not to say that all men aren’t prepared but there are very many men in the legal profession who I’ve had as opposing counsel who aren’t prepared, they just wing it because they can get away with it.

You can’t do that as a woman. I think that people need to recognize that there are a lot of really great women attorneys out there and they need to be taken seriously and given opportunities. That’s not been my experience at my firm but I know a lot of women and have seen a lot of women not being given opportunities.