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20 & Counting

Five Chicago attorneys look back on two decades of life and law

Published in 2024 Illinois Super Lawyers magazine

By Taylor Kuether on February 1, 2024


To mark the 20th edition of Illinois Super Lawyers, we caught up with five Chicago attorneys who have graced our pages over the last two decades: Thomas A. Demetrio, Patricia Brown Holmes, E. Lynn Grayson, Flint Taylor, and—our first-ever cover subject—Robert A. Clifford.

Below, the lawyers recall 20 years of growing, changing, and practicing—and consider what’s ahead.

Practice, Practice, Practice

Flint Taylor, People’s Law Office; Civil Rights: We’ve continued to do the same kind of work—fighting against police violence and white supremacy—that we have done since 1969. But from 2003 onward, I continue to be immersed with several of my partners in the fight to expose the Jon Burge police torture here in Chicago, working with many others to obtain reparations for the survivors that included compensation, a mayoral apology, a memorial, a center for the treatment of survivors and, also, the teaching of the history of police torture in Chicago’s public schools. That was a remarkable accomplishment obtained by an intergenerational, interracial movement that I had the honor of being one of the lawyers for.

Patricia Brown Holmes, Riley Safer Holmes & Cancila; Criminal Defense: White Collar: We started our own national law firm, Riley Safer Holmes & Cancila, in March of 2016. I am the first-ever, in the history of our country, African-American woman to have her name on the marquee, as well as to be the global managing partner, of a national firm.

Thomas A. Demetrio, Corboy & Demetrio; Personal Injury – General: Plaintiff: Generally speaking, the practice hasn’t changed much. We still specialize in personal injury and wrongful death litigation—that’s our main focus and we continue to do that. We have gotten involved, however, in other types of litigation, specifically the NFL concussion cases. We have over 100 NFL clients. I’ve also gotten involved in a bunch of pro bono work.

E. Lynn Grayson, Nijman Franzetti; Environmental: When Super Lawyers talked to me in 2016, I was chair of the department at Jenner & Block. After 25 years I left, and I’m now a partner-owner of a boutique environmental law firm owned by five women environmental lawyers. We are all from big law, we all used to chair departments, and we all have the understanding that the way we want to practice environmental law is better managed in a boutique firm setting. I represent a number of Fortune 100, Fortune 250 and Fortune 500 companies.

Robert A. Clifford, Clifford Law Offices; Personal Injury – General: Plaintiff: I’m as active now in my practice as I’ve ever been. I’m empowering several of my younger partners to help with the growth of Clifford Law and the sustainability of our firm. I hold the view that there’s no reason my firm can’t be active 50 years from now. I’m surrounded by young people who want a future, and I’m determined to help give it to them.


Holmes: What I’ve seen in the last 20 years is a huge focus on equity. There’s been a focus on diversity, and now we’ve started to get a critical mass of women and minorities. People are realizing that you can hire a woman, or minority lawyer, and still get spectacular service. … You’ve got women with children, men with children who want to be with their kids; you’ve got grandparents; you’ve got every race, every gender; you’ve got trans people who are like, “Hey, I can be a lawyer.” And why not? You just didn’t have that 20 years ago.

Grayson: Environmental law is taking on a greater and more prominent role for U.S. businesses—and our international clients, too. I think that’s exacerbated by items that we’re encountering in our personal lives, like climate change considerations, the changing weather patterns, and the concerns over our environment and water quality. There’s a growing awareness and, in my opinion, a much-needed sensitivity and community focus on what needs to happen to protect our environment.

Taylor: I’m becoming older and hopefully a bit wiser. I have always very much been interested in history and what could be called “people’s history,” and I’ve always written about cases I’ve been involved in. In the last five years I have published a book called The Torture Machine: Racism and Police Violence in Chicago, which focuses on the Fred Hampton assassination and the long and winding history of police torture in Chicago. I’m presently working on a second book that deals specifically with systemic prosecutorial and judicial misconduct as seen through the lens of the Fred Hampton case and the Jackie Wilson police torture case.

Holmes: As you get older, you start to become less afraid. I’m older and bolder, so I go for it. When you’re younger, you don’t want to be too passionate because of what someone might think. Now I don’t care what people think. I’m passionate about what I do; I love what I do.

Technological Advances

Demetrio: The pandemic had a big change for our practice on a day-to-day basis, and not in a good way. We’re trial lawyers: we’re people-conscious, we deal with people. Everything became automatically Zoom-related—hearings were held by Zoom, depositions were taken by Zoom, there were even trials by Zoom. In our world, at-home work should not be—and I hope is not—the future. The future should be interactive on a daily basis, both in the office and the courthouse.

Clifford: We’ve become more technology-driven on a daily basis. Certainly, technology has advanced the quality of our practice. But it’s also a challenge to stay up on. The larger the matters you handle, the more likely it is your adversaries are from big law. So, when we go up against the big firms that have vast technology and staffing resources, we have to match that. I still view myself as a small firm and I’ve always maintained that, on any single book of business, I can go toe to toe with those people.

Grayson: COVID was a kick in the pants to making law more sustainable, functional, and flexible for all of us. Being able to conduct hearings, or go to court, in a remote way, I think, is a tremendous advantage that would have been helpful and meaningful for lawyers all along. A lot of offices are moving back toward a certain amount of facetime in the office. Having said that, one thing that came out of COVID was a new awareness and appreciation for the necessity of work-life balance. I think that’s incredibly helpful for women, who tend to bear the bulk of child-caring responsibilities—and, frankly, other family obligations—and I think it’s going to help them build their careers in a big way.

Facing Forward

Clifford: There will always be a need for good trial lawyers: people who know the rules of evidence, understand the dynamics of courtroom activity, and who can prepare and present evidence through live testimony. I don’t see that ever going away, but how we will do it is maybe the thing that will change. We’re going to see continued expansion of continuing legal education, because it’s hard to get experience where there is a decline in the number of jury trials. There are going to be more people spending time in mock trial or mock hearing matters. Even in my offices, we’re currently remodeling one of the conference rooms to make a mini-courtroom. 

Taylor: It’s important to have a support mechanism in family, colleagues, and partners who you work with—and share a common set of principles. The clients, family, and the movement have and continue to give me a lot of motivation, inspiration, and strength to keep going. It’s not always easy to be battling with forces that often appear to be invincible or richly financed. To keep that fight up, you need that support system and belief structure.

Demetrio: I came into this practice at a time when there was terrific camaraderie between the plaintiff’s bar and the defense bar, and I hope that that camaraderie gets reborn. I’ve also noticed that lawyers just don’t seem happy. They’re grumpy. Every little battle needs to be won in the discovery process, for instance, like it’s a major victory. And it’s not. You don’t have to clobber somebody on a daily basis. I would like to see lawyers enjoy themselves more.

Grayson: In 2019 to 2020 I was co-chair of the CBA/CBF Task Force on the Sustainable Practice of Law & Innovation. We issued a report to the Illinois Supreme Court to improve access to justice. There’s a place for everybody in the law, and we need to make sure everyone has access to the justice system when they need it. More people than ever are appearing pro se in court for life-changing situations—housing, family law, collections, debt, all kinds of criminal matters. There’s never too much we can do to improve access to justice, so I am motivated about legal reforms that would improve it.

Clifford: The next generation is really going to have to tackle the AI issue—try to control it as a tool to advance litigation on behalf of clients, and the practice of law. That’s certainly going to be a big challenge. I don’t know how far into the future that is, but it might be right around the corner given how fast technology races forward. In 1984, I started my law firm with one computer and a fax machine; look at where we’re at today in comparison to then. Will jury trials become virtual? Will courtrooms be largely obsolete? We’re definitely going to expand virtual activity in the practice of law in the years ahead.

Advice for the Next Generation

Holmes: Look down the road and desire to be in charge, desire to be a leader, desire to take a firm like this one and shape it into a firm of the future. Grab those reins and just do it. Just grow. Just trust yourself. It’s life, it’s going to happen no matter what, so why not have it happen the way you fashion it? Get in there and take control of your career.

Taylor: I have a lot of respect and hope for the young generation of lawyers—including my daughter who is a terrific federal defender—and I’m always trying to bring what I know to them. There are so many fields of civil rights law that are important to pursue that my advice would be to follow your beliefs, and your heart, in terms of what you feel is most significant. If at all possible, take the road to being a people’s lawyer rather than to fall into the trap, as I see it, of being a lawyer that serves the interests of the rich and powerful. I urge young people to find their footing in the area that they feel best suited for, and that interests them the most.

Grayson: Young people are smarter. They’re brighter. They’re much more focused on their needs, and I don’t think they’re afraid to ask for what they want. They’re in a perfect position to find a place in law that makes them happy and have the tools they need to be successful. My advice would be to find a place you belong. Try to make sure you’re happy, and the rest will follow.

Demetrio: In the last 20 years, there’s been more confrontational interactions between plaintiff’s and defendant’s lawyers. It need not be that way. I think future generations need to be empathetic, adroit, have common sense, not let unnecessary issues enter into any case, and always, always be prepared. You should go to work because you want to actually go to work. And you should get out of the house.

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