From the Football Field to Finance Law: Perseverance in Life and Law with Christopher Stewart, VP & Assistant General Counsel at AIG Investments
In this episode of On Record PR, Jennifer Simpson Carr goes on record with Christopher Stewart, a lawyer and a division one college football player at the University of Notre Dame.
More About Christopher Stewart
Chris is a Vice President-Assistant General Counsel for AIG Investments in New York, New York. Prior to his role in-house, Chris worked as a corporate associate at both White & Case and Sullivan & Cromwell where is practice focused on financing and developing various transactions in the telecommunications, infrastructure, and oil and gas industries. He has acted for many of the world’s largest institutions and corporate entities in several international commercial transactions and has experience advising such clients on various M&A, Private Equity, and Capital Markets related matters.
Chris graduated from Notre Dame Law School. During his 1L year, Chris was credited as being the only law student in the country to play major Division I college football simultaneously, and prior to graduating from Notre Dame Law School, Chris enjoyed an abbreviated career as an Offensive Lineman in the National Football League. Chris also received his Bachelor of Arts Degree from the University of Notre Dame.
Chris is admitted to practice in the state of New York, Texas, and the District of Columbia. He is a proud board member of four organizations—Play Like a Champion Today, Students Bridging the Information Gap (SBIG), Merging Vets & Players (MVP), and the Notre Dame Law School Advisory Council.
Jennifer Simpson Carr: Chris, it’s wonderful to see you today.
Christopher Stewart: Hi Jennifer. Thank you for having me.
Jennifer Simpson Carr: Thank you for joining me. I’m very excited to talk to you about your journey in law and in football. For our listeners, Chris and I have known each other probably longer than either of us remembers. I was trying to think about the first time that we met. I don’t know if you remember.
Christopher Stewart: I don’t either. No. When we were babies?
Jennifer Simpson Carr: Our mothers played together on the 1976 U.S. Women’s Basketball Team, which for our listeners was the first women’s basketball team to represent the United States in the Olympic Games.
So, fast forward many years, Chris and I had the great opportunity to reconnect when we were both living in Arizona at the same time.
Christopher Stewart: Before it got this hot. When it was still bearable.
Jennifer Simpson Carr: We got out of there in plenty of time.
Christopher Stewart: Exactly.
Jennifer Simpson Carr: I know this interview is about you, your experience, and your journey, but I just want to take a moment to plug the beautiful documentary of your mother Lusia “Lucy” Harris titled, “The Queen of Basketball” which premiered at the Tribeca Film Festival. As a former athlete and a mother of a daughter, I am so proud that we continue to tell these stories, these important stories, and honor the women athletes who paved the way for us. I just learned from you that you were behind the scenes working on the film. How was that experience?
Christopher Stewart: It was a great experience, especially having had my own sports career and then to see the entertainment side, the legal side, and the production side. Working with [Greg Warner 00:02:09] a little bit to make sure that they had all the materials they could for our family. I enjoyed it, but I’m not changing careers anytime soon. It’s kind of a one-and-done situation. It was great.
Jennifer Simpson Carr: That’s awesome. What a cool experience. I will put the link to the New York Times documentary in our transcript, and I encourage our listeners to take a look at it. It’s really beautiful.
Christopher Stewart: It’s really nice.
Jennifer Simpson Carr: You have a mother who is an amazing trailblazing athlete and basketball player, and so I want to know:
Where does your love of football come from?
From that, to be honest. I’m originally from Mississippi, and then moved to Texas when I was about 9 or 10. I just remember at a very young age just loving to compete, and whether it was against my siblings and we were playing basketball, or tag or whatever it was, I loved to compete. I think that’s just in my veins, honestly. So, I remember being at a certain age and telling my mom, “I want to be good at this,” and blah, blah, blah. I had no idea what my mom had done. She had these photos of the ’76 team and Pan American team. I just recall at a very young age telling her, “I want to be good at this.” Nerdy kid, in the library reading about all types of things. My mom said something in the documentary that she actually said to me when she was younger. She’s says, “You can do whatever you put your mind to. You can be successful. You just have to work hard and believe you can do it.” I think that’s kind of how it started.
I was a three-sport athlete in high school, from middle school to high school. I recognized kind of early on that football was my thing. I was just really good, I had the body type for it. I actually loved the contact in football and loved playing it. I was bigger than most people, didn’t get hurt as much. Yeah, I think with that competitive streak, that history and then just being good at something, you just kind of stick with it.
What were the other two sports in high school?
Basketball and I threw discus and shot put for track. I was okay at that one. Basketball I was good at, but my body type, I’m definitely a football player. I’m the one anomaly in the family. My brother’s seven foot tall, my sisters are over six foot, but I was the one who was always kind of stocky and already lifting weights, and just be like, “All right, this is what we’re going to do.”
Jennifer Simpson Carr: So, it was your calling.
Christopher Stewart: It was my calling.
The Notre Dame Fighting Irish is arguably the most iconic college football team. What was the transition like for you from high school football to playing at Notre Dame?
Yeah, it was very difficult, to be honest. I actually almost ended up, at one point in my sophomore year, I almost transferred from Notre Dame. I’m glad that I stuck with it. Especially with football, the jump from high school to pros, some people say … Sorry, high school to college, some people argue is harder than the jump from college to pros because there’s like a gap in that time when you come on as an 18 or 19 year old and you’re playing with 21 and 22 year olds, who are now men. The game is so much faster and physical. Some people can adjust to it fast, but me playing offensive line, it took a while. It took me a good two years to actually make that transition, get my body into the kind of shape I needed to be in, and to get down a pro-style offense, with Charlie Weis bringing offense to Notre Dame. It was a very difficult transition but it ended up paying off. It was a strong life lesson, how you have to stick with things in order to be successful.
Jennifer Simpson Carr: I am sure. Having the thoughts to transfer at some point and overcoming whatever doubt or fear, all of those things that come up, just speaks to your work ethic and is a testament to your dedication, so kudos to you.
Christopher Stewart: Yeah. Kudos to my family for putting up with me during that time too, because they were many phone calls saying, “I don’t know if I can do this. It’s freezing outside.” We would have practices at 6:00 AM sometimes, in the middle of January, and they would call it something like mental strengthening sessions. I remember a couple of those sessions; we would have to wait until snowplows came and cleared the snow off the field for us to be able to do these sessions. I’m from the South, I had seen snow maybe like once in my entire life, and here you are at 6:00 AM and it’s pitch black dark and you’re supposed to run around with hardly any clothes on. It was a transition, but I’m happy that I stuck with it and am successful at it.
Jennifer Simpson Carr: That’s great. I appreciate you sharing that story. I think there’s so much hard work that goes into being successful, and that is just one example. Waiting for snowplows to clear the snow… I can only imagine.
Christopher Stewart: I’ll never forget that.
Jennifer Simpson Carr: As I mentioned in your bio, during your 1L year, you were credited as being the only law student in the country to play major division one college football simultaneously.
How did you balance the demands of football and law school?
Yeah. It’s kind of one of those things, you try your best and just pray to God that your best is good enough. That was probably the second challenging thing that I encountered at Notre Dame. I had graduated high school early and graduated college early. We’re always on campus, mostly for the summer training and things like that. If you don’t drop a class, you actually have a chance to get ahead, which I did and so many other athletes at Notre Dame do now. I wanted to spend as much of Notre Dame’s scholarship money as I could and be working towards a career afterward.
Talk about not sleeping… I just kind of survived, to be honest. There were times where I would wake up for those 6:00 AM workouts, then had to go to class, and come back from practice. Then, I had my student job and would study until 1:00 or 2:00 AM just to try and keep up with the law school curriculum and 1L. I don’t know if you can tell, but that’s where my gray hair started, during that time. Some people get it later in life, I got them playing football and going to law school. I just juggled it as best I could.
Always had a rule that when it was time to go to a game, on the Saturdays, Fridays we would travel, I just did not bring any school work. I had to set that boundary in order to be ready for the game, which put me behind by a day or two in the schedule of being up on the week to stay ahead of the hundreds of pages of reading that you have. Then, I just had to catch up Sunday through Thursday and do the best I could to be ready for the exam. I was the first one to do it, and I think the only one to do it so far. I think there was a reason for that. The two should not go together. They are not meant to be done. I have warned people multiple times. I don’t know if there were a thousand lives to live if I would do it again.
Jennifer Simpson Carr: Well, you made it through and you’re in the process of an amazing career right now.
What inspired your passion for law?
Yeah. It’s funny, I kind of fell into law. Going back to the story I mentioned earlier of graduating early and wanting to do something, I actually thought that I wanted to go to business school and that B-school would be the better fit for me. I’m a little bit more personable and want to know how the operations of how things work. I knew I wanted to stay at Notre Dame to finish my football career, and I gave a fleeting thought very quickly about possibly going somewhere else to do that, but decided to stay and do it. Basically, the business school was like, “We don’t think you can do this. This schedule doesn’t make sense.” There’s a professor at Notre Dame Law School named Patricia “Tricia” Bellia, and she and her husband are former Supreme Court clerks. She set up the faculty board for athletics, which is our governing sports body on campus that kind of has each person, each head of a faculty, including the president and athletic director on this board oversee athletics to make sure academic standings are up to par.
I was in grad school already as a non-degree student. Tricia said, “If you want to give it a shot in law school, we’re happy to work with you. You have to get into law school the same way as anyone else, but you can take a couple of classes while you study for the entrance exam, the LSAT.” I was like, “All right, I’ll give that a shot.” So, I did it.
I started taking classes. I think I took a class with a professor named Mark McKenna who also played football at Notre Dame. Yeah, that’s what kind of started it.
So, I kind of fell into it, and then along the way was like, “Okay, I can do this. I think this can be a career thing, that I kind of leverage this to also do corporate law and kind of understand the same things I was looking to do with business school.” I fell into it and realized that, as a Virgo, I’m very much predisposed to be a lawyer. We’re very analytical people, so it worked out. I kind of found my way as I went along the path, which is a life lesson if I ever heard one.
Jennifer Simpson Carr: That’s true. I think we are all always trying to find our way through life.
What areas of law do you enjoy most or interest you most?
I’m very much interested in corporate law. If I were to distill it to kind of one phrase, it’s, “follow the money.” I love to learn how things are financed. I’ve done private equity financing, like capital markets, and most recently in the last two and a half years have been doing project finance and development. Kind of doing infrastructure finance is like a buzzword now with the new administration. I’ve always been very interested in the access to capital and how companies and businesses do that. So, in doing that, I really enjoy the finance part of my work. My fiancée is the CEO of a startup and sometimes we’ll be talking about what she’s doing in the infrastructure space, especially in the products she’s making. I love that advisory aspect of it. Once you kind of learn the ropes and the rules and the regulations of how financing works, it’s just about trying to figure out how to help people get access to capital, to realize their vision. I really enjoy that part, about the field. So, hopefully it will go well.
Do you leverage your legal experience to support any passion projects?
I do. One, there’s stuff going on with my mom right now and her kind of resurgence and renaissance and her career is one thing that’s been pretty awesome. To just kind of help out with some of her contracts, and be able to also advise there and say, “I have a friend who’s in this kind of entertainment and they think you should do X or that you do Y.” That’s fun, to help my mom out and to make sure that she’s getting her just due in these projects that are coming up.
One of the other things I enjoy doing is helping people who have been convicted of non-violent drug offenses actually get out of prison as marijuana laws, things like that, are deregulated and decriminalized. My pro bono work for quite some time now has been kind of focused on that, helping kind of stem the tide of mass incarceration. Where people were just caught up in this unfortunate Drug War, but haven’t done anything that’s violent, per se. To help them to be able to get released, avoid recidivism, keep those rates low, and try to move on with their lives. Especially as we as a society have changed and decided that marijuana is not something that we want to lock people up for. So, that’s a big part of it for sure.
Jennifer Simpson Carr: That’s wonderful. I always love to hear about the pro bono work that attorneys do, because you have such a unique skillset and education. To hear that you are offering those services to help individuals’ kind of restart their lives and have a second chance, especially given, as you said, the laws are changing on the position on marijuana and its use. Thank you for that. That’s an amazing use of your time and your skills.
Christopher Stewart: It’s difficult, but it’s kind of rewarding to see when people actually do get released. You hear some stories of people being like, “I’m in jail by state laws for like five, 10 years for things that in some states today no one would even blink if they saw you with that.” I love to think that we’re helping do things to move our society forward.
Can you share any lessons that you’ve learned throughout your playing career that inform the work that you do now as an attorney?
Sure. I would say the main thing, honestly, is perseverance kind of sticks out in my head. So many times in sports, especially when you’re playing something like offensive line, it’s like … I forget what Bruce Lee said, “You don’t fear the person who’s done like 10,000 kicks, you fear the person that’s done that one kick 10,000 times.” Become an expert at it. In my opinion, it takes the same amount of dedication and day in, day out grinding to just try and be as good as you possibly can at this profession. They call it a practice for a reason. You try your best to be informed. You try your best to advise as best as you can and make sure that people know where the line is and how to navigate and not fall on the other side of it, but it takes a lot of work. It’s a lot of work, and time literally is our modicum of value and payment in this profession. Everything is billed, or whatever, by sometimes 15-minute increments, or sometimes six, which is insane. If there’s anything that I think sports has helped prepare me for this profession, it’s definitely that day in, day out grind. I have friends in private equity who would say the same thing. It’s the same feeling but it’s a lot of work and a lot of time.
You’ve worked in a number of very prestigious international law firms, and knowing what you do now, what advice would you give yourself as a first-year associate?
The first thing I would tell myself is, “It’s going to be okay. Step one, breathe.” So much of coming into a law firm, especially these top firms in New York, it’s just like it’s kind of you get hit in the face with the amount of prestige and work and the sheer volume of what you’re doing, and you’re just so terrified not to mess up. At least I was, as a first-generation attorney. And you’re sitting here and you’re being paid this handsome salary but you’re working all the time, and the biggest worry is, “Oh dear God, I don’t want to mess up and I don’t want to get fired for messing up.” If I go back and I tell myself … I tell this to some of my mentees too, who are summers or first year associates. I just tell them, “It’s going to be okay. One, no one’s going to give you so much work that you’re going to make the firm go bankrupt.” It’s a little bit training wheels are on a little bit. You don’t see them.
Two, I would just say, it’s going to require a lot of time. Time, it just takes time. It takes so much time to really grasp the level of deal work and the complexity of what it takes to succeed on this level. It’s almost like a little light. It will start out this small, and as you keep practicing, it kind of opens up. You get your periphery. Over five- or six-year period, you kind of know what’s going on.
Then the third thing I would say is kind of enjoy the ride. Because of one and two of it being a fear of messing up, realizing that it takes so much time to be successful, I wish I had kind of stopped and smelled the roses a little bit as I was going along that journey, because, especially after Covid, you just kind of realize you get one shot at this life, as far as we know, so enjoy it. Even if that requires longer hours, some time away for family, really enjoy that time with family. Now, as a more senior attorney, like in my 6th year of practice now, as much as I can possibly be off when I’m off, I try to be off and spend time with family, spend time with my fiancée, actually do things that I’m going to remember in life as I get older and make those impacts. Because at the end of the day, that’s really what matters.
Jennifer Simpson Carr: I love those answers, and I think they’re absolutely applicable to law firms, but I think all three are applicable to life. I love the idea of, “It’s going to be okay.”
Christopher Stewart: It’s going to be okay. It really will be okay. I didn’t feel like that until, honestly, until recently, the last few years, where I’m just like, “You know, it’s going to be okay. You always feel like you’re doing something …” When you’re a first-generation attorney, you feel like there is no rubric really and you have to find mentors and things like that. At some point you just say, “It’s going to be okay. Just keep moving forward.”
Jennifer Simpson Carr: That’s great. Well, Chris, thank you so much for your time today. I really enjoyed our conversation. I just very much appreciate you taking the time to chat with me about your experience.
Thank you for having me be on your program. This has been kind of great to mix the two. Thank you a lot.
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