Hall of Fame Lawyer Limelight: Robert Riley

If you ask a four-year-old what they want to be when they grow up, you’ll probably receive an answer like:


“Dinosaur expert.”


At that age, Bob Riley wanted to be a lawyer.

He looks back on his earliest memories, before he had even started elementary school, and sees his father standing in the well of a courtroom. “I don’t know what case he was arguing or why I was there. Maybe my mom and I were just meeting my dad for lunch,” remembers Riley. “But the courtroom left an indelible impression on me. Growing up, I had this notion that that’s what I was born to do. I never seriously considered another path.” From day one, Riley has been a trial lawyer, through and through.

Right out of law school, he sought that trial experience at Schiff Hardin, where he’d spend the next three decades of his career. Riley built an impressive defense practice representing clients in complex product liability, white-collar, mass tort and environmental cases, developing a substantial appellate practice, as well. From early product liability and mass tort litigations to chairing the firm for ten years, Riley built a career defined by exceptional advocacy and leadership. Then, in 2016, it was time to continue that standard of excellence in a new way. 

He and a group of attorneys at the firm, including Ron Safer, Patricia Brown Holmes and Joe Cancila, saw the chance to create a law firm from scratch – a pillar of excellence defined by service to the client and the attorneys who worked there. A firm where diversity would be integral to excellence. A firm where pro bono clients would be treated with the same level of respect and dedication as Fortune 500 clients. They created Riley Safer Holmes & Cancila.

“I admired everyone’s courage in pulling together in the pursuit of this idea that we could create a firm that’s different from every other firm out there,” Riley says. In the last seven years, the firm has grown from a group of 22 attorneys with a vision to a firm with five offices in Chicago, San Francisco, New York, L.A. and Ann Arbor, Mich. tackling major white-collar litigation. In the first year after the firm’s founding, Riley successfully argued two cases in the 7th Circuit Court of Appeals.

The Lawdragon Hall of Fame member says that a career trying cases has matched his childhood dreams. “There’s nothing like it,” Riley says. “The role of a lawyer in a jury trial is the epitome of what we’re supposed to do: serve our clients and serve the system of justice as officers of the court. It’s everything I wanted it to be.”

Lawdragon: Your firm started with this idea of a blank slate – creating an inclusive place that would make people happy to practice there from the ground-up. How did you go about achieving those principles?

Robert Riley: Whether we're achieving them is determined in the eyes of all my colleagues. But we started the firm to be one with an uncompromising commitment to professional excellence in the service of clients. A lot goes into that. For example, our commitment to diversity.

LD: Tell me about that.

RR: Diversity is part of our commitment to professional excellence, which we define as tapping a wide range of exceptionally talented people who are empowered to bring their diverse perspectives and backgrounds to benefit our clients.

As diverse as we are, we all have the same mission. We serve clients at the highest conceivable professional level, and we believe our diversity empowers that, as opposed to it being some goal that's independent of the core mission of the law firm.

LD: What do you look for in bringing on people who will commit to that vision?

RR: That may be the most important question for the firm over the long-term. We want to continue to attract, identify, recruit, develop and retain people who share that common set of characteristics.

Everyone we look at is smart and has credentials, but what we’re looking for, in addition to that, are the intangibles. What have they confronted and overcome in their lives? How have they demonstrated resilience? What's their level of commitment?

We rely on everybody being all in because everybody bears a lot of responsibility for the success of a young and growing firm. That gig isn't for everyone, and that’s fine. But we want somebody who's courageous enough to say, "I get what you're doing. I want the challenge.” And believe me, you find those characteristics in a widely diverse group of people.

LD: How would you describe your style as a lawyer?

RR: I would be the worst person in the world to describe my own style. If you try jury cases, you know what matters is what the jury takes away about the client's cause. You're the vehicle through which the client and the case are viewed. It’s important to understand the humility that requires because you’re not really in charge. The judge is in charge of the courtroom and the jury is in charge of the outcome.

So, I view this as a service profession at all levels. You're serving your client; you're serving the court; you're serving a jury who's charged with this awesome responsibility. Your job is not just to be an advocate, but to empower the jury to do the right thing. If you think about it that way, it helps you avoid that narrow view of a lawyer’s job solely as the mouthpiece of the client.

LD: We spoke with Ron Safer last year, and he described you as strategic and dogged.

RR: Well, Ron is the trial lawyer everyone aspires to be. He has an unmatched commitment to the process and to our clients. He is a generational talent in the courtroom and an extraordinary leader in our firm and in the profession.  He is also one of the best people I know.

LD: What do you admire about the other named partners?

RR: Patricia Brown Holmes is a force of nature. She is a brilliant lawyer and strategist. There's not much in the law she hasn't done. Her judgment is impeccable. She is a powerful presence in any room in which she sits. Yet, I suspect she'd be the last person to claim that that's true.

Joe [Cancila] is the quintessential lawyer's lawyer. He is analytically precise and deeply dedicated to the client's cause. He doesn’t leave a stone unturned, a thought unconsidered. He is careful, deliberate and has an outstanding legal mind.

I am proud of the fact that all of the lawyers in our firm have an unparalleled commitment to professional excellence that mirrors the commitment of Ron, Patricia and Joe. My colleagues are not just smart, they embody the resilience, commitment, courage and drive that differentiate lawyers who can and will try a case to verdict. 

Ed Casmere is a great example.  I tried a case with Ed when he was a first-year lawyer.  Along with every other task imposed by the trial, I gave him two witnesses to examine, and he never flinched.  He is immensely talented, has a natural touch with a jury, and has never stopped pushing himself up the learning curve.

I view this as a service profession at all levels. You're serving your client; you're serving the court; you're serving a jury who's charged with this awesome responsibility.

LD: What initiated your decision to start a firm together?

RR: A multi-generational group of us said, "We can continue to practice at the highest level, but we can do it in a law firm that walks and talks differently.”

We think clients want a law firm that is more closely aligned with the priorities of the people we serve. Large institutional firms are powerful for a reason, but they can be inward-looking because you have to run a big organization in a certain way. Starting a law firm from scratch allowed us to focus almost exclusively on what serves the client.

LD: What has changed since the firm’s start?

RR: We quadrupled the size of the firm in a relatively short period of time. There's an imperative that we continue to grow because we're fortunate to have clients who demand our services, and we have to be positioned to meet those demands. That means that we need to continue to attract multi-generational talent so that whoever shows up from Riley Safer Holmes & Cancila at whatever level of experience is going to be the best lawyer at that level of experience you’ve ever seen.

LD: Tell me about that emphasis on multi-generational talent. Why is that so key?

RR: Unlike a lot of firms that start with a couple of contemporaries, we started with people whose ages ranged from their 30s to their 60s. That gives you a breadth of perspective. It also tells clients right out of the gate that the people founding the firm have a long view.

If the firm has a legacy, it’s going to be the people who emerge over time as lawyers with a full skillset –amazing lawyers who can carry the firm forward long after I'm a distant memory. That's what you hope for; that's what you form the law firm to become; that process has already started.

And if I have any legacy in the practice of law, it resides in the people that I've practiced with from their first days out of law school. If I have made any contribution to their careers, it has been to trust them with opportunities that have allowed them to make themselves into exceptional professionals on every level.

LD: Would you say then that mentorship plays a significant role in your practice?

RR: I hope it does. Again, the people who would judge that are the people I'm working with.

The real learning happens in the trenches. I try to lead by example. Being part of a team where everybody brings his or her best to the table in the service of the client – that's where the real mentorship takes place.

The practice of law is an apprenticeship model. I'm working with some young lawyers now who are amazing. They're talented and gritty and committed. Hopefully, they recognize that you're always going to be learning; you're always going to be trying to improve your craft. If that takes root relatively early in a lawyer's career, it'll never leave that lawyer, in my experience.

LD: Do you have any specific examples of learning that takes place on your feet?

RR: One is being able to hear yourself in court or a deposition with “transcript ears.” It's not what I thought you said – it’s what you actually said; it's what I actually ask. The precision that demands as a questioner who frames clear questions and insists on clear answers, is a cardinal lesson.

If I have any legacy in the practice of law, it resides in the people that I've practiced with from their first days out of law school.

LD: Taking a step back, which cases you’ve tried during your career really stand out in your memory?

RR: They all do.

I've spent a career trying complex cases across the country – cases that lasted for months at a time against extraordinarily gifted lawyers on the other side. I've tried cases against the late Ron Motley, Mark Lanier and Perry Weitz, who are some of the most accomplished people in the plaintiffs’ bar. I’ve worked on cases with incredibly talented lawyers outside my own law firm, like W.G. Watkins from Mississippi, Bruce Shaw from South Carolina and Steve Johnson from the Pacific Northwest. I learned a great deal about my craft in every one of those experiences.

LD: What did you learn?

RR: I learned about the weight of responsibility imposed by a client’s trust to stand in the well of a courtroom on their behalf. I learned about the importance of credibility in doing so. I learned you can disagree without having to be constantly disagreeable. You can forge relationships even with people who are on the other side of the bar. I'm proud to say I have developed relationships with people on the other side of cases where we fought hard and long. I want to practice with the best lawyers I can find, and I want to test myself against the best lawyers in the profession.

LD: What else has made your cases fulfilling?

RR: Whether you're trying a case in a big city or a small rural community, there's something common about a jury trial. You have to find a way to establish credibility in the courtroom with a judge you've never seen before and with a jury of people who come from that community.

LD: How do you do that?

RR: You have to be your authentic self. If I were to try to affect a voice mimicking those around me, I'd be phony and everybody in the room would know it. I tell them who I am and try to convey that I'm going to try to earn the right for them to listen to me. You have to earn your credibility, and there's a certain humility that comes with that.

LD: Tell me a bit about your substantial appellate practice.

RR: That's been a tremendously rewarding part of my career because it's gotten me in front of the Illinois Supreme Court on multiple occasions, as well as the highest courts in New York, Oregon, Maryland, Wisconsin and other states. I have argued repeatedly in various Federal Courts of Appeal.  I've had the same kind of national scope in my appellate practice as I have in my trial practice. The same amount of preparation and hard work is required. The burden of the client’s trust is the same. Your command of the facts and the law has to be complete.

LD: What are the differences between your trial practice and your appellate practice?

RR: Oral advocacy in an appellate case is not about arguing with anybody. The point is to try to persuade the bench to consider the path that's going to lead to the result that your client needs, while shaping the law in a rational way.

When I'm asked to talk about appellate advocacy, I always try to explain to people that a question from an appellate panel, even if it sounds hostile, is a gift. It tells you what the court's concerned about and gives you the opportunity to address that, which you should embrace. Once, a judge said, "It sounds like you expected that question." My response was, "Your Honor, I hoped for it.”

LD: How did you learn to look at appeals that way?

RR: The first time I argued in the 7th Circuit, I was interrupted between saying “good” and “morning.” I got questions nonstop, and they were not softballs. When my time ran out, the chief judge of the 7th Circuit looked down at me and he said, "Counsel, was there anything that you had wanted to say?" I smiled and I said, "As a matter of fact, there was, Your Honor.” He said, "Why don't you take a couple of minutes to say it?"

A question from an appellate panel, even if it sounds hostile, is a gift.

LD: That’s great.

RR: That was Judge Cummings. He's going to live in my heart forever because, as a kid lawyer, he gave me that little bit of leeway.

LD: What continues to excite you every day about your practice? Has it changed since the beginning of your career?

RR: Having the privilege of representing a client in a system of justice I revere is what's motivated me through my entire career, and that'll never change for me. I was lucky to find that path early in life and commit to it. I’m proud that, from where I sit now, I can say that with conviction.

LD: What else are you proud of?

RR: I'm proud of my wife and my kids. I'm proud of the people that my kids have become. I'm proud of my grandchildren. My family has been central to me throughout my life. I'm proud of my professional life and what I've tried to achieve, but my family's always been first to me.