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Neck to Neck: Two Generations of Leathernecks Meet to Discuss Their Paths
October 10, 2025
From the pages of the Summer 2025 ´şÓęÖ±˛Ą Illinois University Alumni Magazine—this story is part of our special series of feature articles. View the full issue at .
CHICAGO, IL - - On a dreary morning in early 2025, two men met for the first time at a conference table on the 43rd story of a downtown Chicago skyscraper. As the clouds filled the windows with a blanket of white, the two chatted about their time as WIU students, their experiences as fraternity men and their interests in law careers.
Joseph Zaylik graduated in May with a degree in business analytics and a minor in pre-law. He is the recipient of the Dan and Laura Webb Pre-Law Scholarship, the Ernest J. Codilis, Jr. Pre-Law Scholarship and the Keith Webb Memorial Scholarship. In April 2025, Zaylik was named the recipient of the William E. Brattain Award, the most prestigious student leadership honor awarded at WIU.
Dan Webb attended WIU in the 1960s before pursuing his Juris Doctorate at Loyola University Chicago School of Law. He received the WIU Alumni Achievement Award in 1984, the Distinguished Alumni Award in 1992 and an Honorary Doctorate in 2007. Webb served as Special Counsel in the Iran-Contra affair. A highly sought after and successful trial lawyer, he is currently a partner and co-executive chairman at Winston & Strawn LLP.
Throughout his career, Webb has represented Bill Gates, the New York Stock Exchange, General Electric, Philip Morris, Verizon and Boeing, among many others. In 2017, he represented Beef Products, Inc. obtaining over $177 million, the largest ever settlement in the United States for a media defamation case.
This conversation has been edited for length and clarity.
JZ: First, thank you so much for taking the time to meet me today and for the pre-law scholarships you have established. They have been incredibly helpful for me.
DW: Absolutely. It's my pleasure. Tell me a little about yourself.
JZ: I’m from the south suburbs of Chicago, about an hour straight south from here in Steger. I went to a small private high school and had a graduating class of 21.
DW: And had you already decided to be a lawyer when you were still in high school?
JZ: I knew I had an interest in helping people and making a difference in the community. By the end of my freshman year, I knew I wanted to be a lawyer. I got involved in mock trial, student government and a fraternity, and my time in all of those solidified that this is what I want to do.
I greatly enjoyed mock trial and learned so much from that program. I was the student body vice president for the 2023-24 school year and just finished up my term as president of my fraternity last semester. All of those helped solidify that I wanted to help people by being a lawyer.
How did you decide to attend WIU?
DW: I grew up in a small town, Bushnell, IL. I was very smart and I was very uncontrollable. One day, the guidance counselor, a woman named Josephine Johnson `55 MS Ed `58, called me into her office because of a fairly major disciplinary behavior pattern that I had gotten involved in. She basically said, “Look, you’ve got to straighten out your life. I watched you last quarter in debate class. You were hell on wheels. You knew what you were doing. The gap between your brain and your mouth is short. Why don’t you think about becoming a trial lawyer?”
This woman could have been from Mars as far as I was concerned. She bought me three biographies about great trial lawyers with her own money and told me to read them and said I could do what they did. I thought she was out of her mind. In any event, I actually read the books and I thought “Wow, that is kind of me. I like being out there, arguing with people; I like debating.”
So in any event, I made up my mind in high school I wanted to be a trial lawyer. I wanted to be like Clarence Darrow or Louis Nizer. At the time, WIU had a 3+1 partnership with University of Illinois where you start law school after three years of undergrad and finish both degrees at the same time. So I started at WIU. At the end of my junior year, U of I announced they were ending the program. I was devastated.
JZ: What did you do?
DW: I didn’t go back to WIU when the semester started. I started sending out my resume to law schools and got an interview at Loyola in Chicago. I took the train, had never been to Chicago in my life and I didn’t have any money, so I had to walk to Loyola. I met with the dean and as he’s looking at my transcript, he turns to me and says “I’m so sorry. You don't have an undergraduate degree. I misread your transcript. WIU is on the quarter system.”
I said “Sorry is not enough for me” and I gave the best closing argument of my life. I talked my way into law school that day.
So Joseph, the moral of that story is there are going to be opportunities and breaks that come along and you need to take advantage of them. This wonderful woman, Dr. Johnson, gave me the biggest break she could and that led me to a break from Loyola and that led to me sitting here in this chair today.
JZ: That’s an incredible story.
DW: Now, what about you? What do you think your goals are for your first job after law school?
JZ: Honestly, I just want to be a sponge. What attracted me the most to law is the continual learning. New things are constantly happening; you’re the first person on the phone battling issues; and things are different every day. So I want to learn as much information as possible. I’ve had a couple of mentors at ´şÓęÖ±˛Ą who have helped me a lot, so I have a couple of people I can go to for advice. I just want to be the best that I can be. What did you do during your time at WIU to help you prepare for law school?
DW: I did two main things at ´şÓęÖ±˛Ą, I worked my butt off studying and I was a resident assistant in Lincoln Hall. I got to meet so many people and I loved the diversity of the campus. I had never been to a big city, Macomb was big for me at the time, but I met so many students from Chicago and other places. I enjoyed just mingling with people who were new and different from me. It just opened my eyes to what a great and wonderful world it is. We didn’t have anything like mock trial back then. Tell me about that experience.
JZ: Absolutely. Mock trial has given me a lot of cool connections. My freshman year, I didn’t meet anyone who had the same major as me. But with mock trial, I had the opportunity to meet people who were also pre-law and had the same goal of going to law school. So that immediately felt like a community.
DW: That’s phenomenal. And you said you’re in a fraternity. I was in Delta Sigma Phi. Fraternity life gives you the opportunity to meet a lot of people. Do you find that to be fulfilling?
JZ: Yes sir. I’m in Pi Kappa Phi. That’s really where everything started. Members of the fraternity vouched for me to get onto the Student Government Association cabinet and encouraged me to get involved in a couple of other student organizations. Some of the men were very involved and they encouraged me to get more involved on campus because they saw that I had a lot of leadership potential.
I have one last question for you. What is
your favorite trial you’ve been a part of?
DW: That’s a hard one. I’d probably have to say the trial that put me on the map, Operation Greylord. I was two years out of law school and in my second year in the U.S. attorney’s office. We indicted 23 police officers, from the commander on down, for organized crime and corruption. The trial went on for four months with lots of media attention. It was a huge victory for a young kid like me and it definitely put me on the map.
JZ: Dan, thank you so much for chatting with me today. This has been amazing.
DW: Thank you, Joe. You have a really bright future ahead of you. If you’re back in the area this summer, let’s get lunch.
Posted By: Drew Donahoo, University Relations
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