Alumni Spotlight: Stephen V. D’Amore (JD ’94)

I did not think I was going to become a lawyer when I started college. That said, I knew I wanted to do something related to the legal profession. Initially, I started at Loyola in their criminal justice program and quickly realized that was a great path to becoming a police officer. While an honorable profession, that was not the route I wanted to take. Looking to make a change, I sought advice from a Jesuit, Father Bireley, who was head of the history department at Loyola. He suggested political science for me, which he described as history for slow learners. His joke aside, I actually did end up graduating with a political science degree.

DePaul Law was the right place for someone like me from a modest, blue-collar background. A Chicago school based in a Catholic tradition with a reputation for excellence that was within reach for me. That’s why I ultimately landed at DePaul and, of course, there was this gal I really liked that was going to DePaul as well!

Q. What were some of your notable experiences at DePaul Law (classes, professors, student organizations, etc.)?

Like many attorneys, there were a handful of professors that had a profound impact in shaping my thinking about the law and the legal profession. First and foremost, was Professor Elliott Abramson.

Professor Abramson was my first-year contracts professor. If you have seen the movie The Paper Chase, he was a carbon copy of the law professor in that film. He taught me about the importance of critical reading and analysis. I have kept only one textbook from law school and it is my first-year contracts textbook. My practice is commercial litigation and contracts is the foundation of commercial law. As described in the introduction of that textbook, contracts also served the purpose of teaching students how to think like a lawyer. Beyond his contracts class, Professor Abramson emphasized to his students the importance of other great disciplines outside of the law. For him, this was literature, music, and Brooklyn Dodgers baseball. Professor Abramson and his class shaped the way I felt about becoming a lawyer and was among the most significant experience during my time in law school.

The other professor that was outstanding was Professor Michael Jacobs. He was my first-year torts professor, and then antitrust teacher. I clerked for him and we have remained friends. Professor Jacobs attended our wedding. He was influential in teaching me about the intersection between the law and American business. Torts was the worst grade I received in law school and Professor Jacobs gave it to me. Yet, I still loved him.

Q: You started at Winston & Strawn as an associate, how has the firm changed over your 25-year tenure?

Actually, I started at Winston & Strawn as a summer associate in 1993. Since that time, a great deal has changed, however the traditional values of the firm have not.

When I first started at the firm we had roughly 300 lawyers in offices across the United States. Currently, we have nearly 1,000 attorneys practicing in the United States, Europe, and Asia. I’m responsible for the litigation department—we have litigators around the world. The firm has expanded quite a bit over my time, with lateral acquisitions made from many great law firms and organic growth across the globe. In addition, our practice has evolved from being mostly litigation based, to approximately a 50/50 mix of transactions and litigation.

What has remained the same throughout the years and what drew me to Winston & Strawn to begin with are the firm’s values. Winston & Strawn has a deep commitment to legal excellence. Furthermore, we have a passion for client service and a level of humility that makes me proud of my colleagues and my practice. Since I’ve been here, the firm has celebrated its 150th Anniversary and I look forward to hopefully celebrating the 175th Anniversary. Winston & Strawn is a remarkable place and I’m privileged to be part of the firm.

Q: How has the Covid-19 pandemic impacted your practice, cases, and client interactions?

My practice is primarily a trial-based practice. Covid-19 has severely impacted the courts. The last trial I had was in February of 2020 and it was suspended. It will not be completed until later this year. This has caused the biggest impact on my own practice and the litigation part of our firm because the trial practice has been nearly stopped by the virus. For attorneys like myself who enjoy spending time in the courthouse, that aspect of the job has (at least for now) mostly disappeared.

Video conferencing has come to dominate almost every interaction that we have internally and externally with our clients. What has come into focus for me is the importance of purposeful engagement with my clients and colleagues. As opposed to the transactional engagement of the in-person office environment, you must now direct yourself to engage with people in way that is very different than in the pre-pandemic world. In terms of productivity, our firm has remained quite productive. My colleagues have found other things to fill their time. For example, a great deal of time has been shifted to counseling work, as opposed to pure advocacy work for litigators.

In my administrative role with the firm, I feel very much a sense of urgency to be engaged with the people in my department that I am responsible for managing. In a big law firm with great people, the operating assumption had always been that people are going to take care of engagement themselves, do their work, and perform. What has changed since the pandemic started is that we have to think about the personal engagement that we took for granted when working together in the office. We transitioned to being fully remote over the course of a weekend and without any technical issues. People are productive and working, but engagement is something we have to be very purposeful about.

As I look ahead here in 2021, I believe there’s no possibility that things will return as they were pre-pandemic. I believe we will be living forever in an altered working environment. Remote work will be normal and expected. During the course of the pandemic, I have had many hearings, including arguing in the United States Court of Appeals for the Ninth Circuit over Zoom. A year ago, that would have sounded like arguing a case on Mars. What we have learned is that much of the work we previously assumed had to be completed in-person can be done remotely.

That said, getting back into the office and having the interactions we had with our colleagues in the hallways or while getting coffee is still important. An example that comes to mind, which cannot be achieved on Zoom, and that we just cannot lose, is when someone produces a terrific piece of work, the ability to walk into their office and just give them a high-five without having to say anything. That’s meaningful and impactful for the people you work with; it’s a microcosm of so many other things we have to fight to preserve.

Q: What advice do you have for today’s law students?

There’s never going to be a substitute for a deep, deep commitment to legal excellence. Your number one job as a law student is to be an excellent law student. Everything else is secondary, by a lot. The greatest indicator of success after law school is success during law school because it is the time you learn the skills of a lawyer and thinking in a way that the law requires. No matter what else happens in the world, the importance of hitting the books, critical reading, and a focus on being excellent in the technical aspects of your studies will be unchanged.

Beyond that, it is anyone’s guess the skills necessary to be developed on top of legal excellence that will be important for a changing world. To me though, it comes down to three things. First, being excellent in your craft. Second, is being passionate about client service. Your clients need to know that you are in it with them. You are doing what an attorney should do, which is pouring yourself into their problems, from their smallest issue to the largest. And, lastly, you need to possess a humility about yourself and the work you are doing.

Q: You are involved with a number of different community organizations. Tell us more about your volunteer activities?

The two community organizations that I presently devote my time to outside of work and family are the Chicago Symphony Orchestra (CSO) and Gilda’s Club Chicago. I’m on the board of directors for both not-for-profits.

The CSO has been severely impacted by the Covid-19 pandemic. No major performances have occurred in Orchestra Hall since March, and yet, the CSO has survived and thrived. For me, the devotion to music and the arts has been important throughout my life. It is another expression of excellence that allows you to go beyond your everyday situation and experience beauty that is rare. Chicago has the best orchestra in the country, maybe the world, and so I’m passionate about supporting the CSO.

Gilda’s Club Chicago is a cancer support organization. Many women in my family have been impacted by cancer. It is an organization that means a lot to me and is named after the late actress Gilda Radner, who quite famously was a warrior against cancer.