An interview with lawyer and Assistant General Manager of the Columbus Blue Jackets, Josh Flynn
Jon Cooper, Brian Burke, Laurence Gilman, and Josh Flynn. What do these people have in common? For one, they all hold, or formerly held (sorry Brian), high-level positions within NHL organizations. However, there’s something else that links these men. Jon Cooper, Stanley Cup Champion and head coach of the Tampa Bay Lightning, graduated from Thomas M. Cooley Law School. Brian Burke, Stanley Cup Champion and former general manager of the Toronto Maple Leafs, graduated from Harvard Law School. Laurence Gilman, contract negotiation expert and current assistant general manager of the Toronto Maple Leafs, graduated from the University of North Dakota’s School of Law. Last, but certainly not least, Josh Flynn, current assistant general manager of the Columbus Blue Jackets, graduated from Sturm College of Law at the University of Denver. These NHL executives have all used their law degrees to advance their careers.
As an avid sports fan and law student, the use of knowledge and skills acquired in law school to further a career in sports sounds appealing. Following my interest, I thought that it would be valuable to speak with one of these men in order to learn more about how a legal degree can help one’s career in sports management. I recently had the pleasure of interviewing lawyer and assistant general manager of the Columbus Blue Jackets Josh Flynn. I found that the insight and advice Josh provided during this interview were invaluable and I hope you all do as well. The interview is transcribed as follows:
Cristian: What was your law school experience like?
Josh: I went into law school with a very open mind, knowing that I wanted to get into the hockey business somehow. I just tried to keep my eyes open, take in whatever I could, and embrace the experience. In my second year, I started getting involved with an internship at Kurt Overhardt’s firm [Kurt Overhardt is the founder and CEO of KO Sports agency] and broke into the hockey world that way.
Cristian: What kind of work did you do for Kurt?
Josh: Mainly all of his negotiation prep work, preparing arguments for him, sitting in on some of the negotiations with teams, stuff like that. I also did some work on endorsement deals, but the main part of my job was helping him prepare and negotiate contracts for his clients. His firm had contacted my school looking for students and I got in that way.
Cristian: What does your day-to-day look like as the assistant general manager of the Blue Jackets?
Josh: It’s impossible to answer – one day never looks the same. Right now, we’re in the middle of signing season. If we had any arbitration cases, I’d be working on that with our arbitration counsel. But since we don’t have any players that filed for arbitration, I’ve been on the phone today with different agents for different players that are Restricted Free Agents, trying to get some deals done. So, I’m doing a lot of research, talking to agents, negotiating contracts, looking at our cap fixture and the league’s cap fixture and working with our management group to help strategize what our next move might be this summer. When we’re normally playing hockey in October, not a lot of contract stuff goes on between opening day and in-season and it’s not too busy a time in terms of team transactions. My day-to-day is really dictated by the time of the year. But right now, I’m really using my law skills more – negotiating contracts and crafting arguments to use to help justify what we think players should be paid.
Cristian: I can see how negotiating skills gained in law school can come in handy during contract negotiation time.
Josh: Definitely. In my third year of law school, I participated in an arbitration and mediation clinic. We usually dealt with small claims but the clients would come in and we’d try to mediate the dispute, so that was a good experience in my professional development. At the end of the day, nothing is really different if you’re dealing with $1,000 worth of auto damage or if you’re negotiating a $10 million dollar player contract, the principles are the same.
Cristian: You mentioned that life can be pretty nomadic during the season as you travel around watching all the games you can. How has this impacted your work-life balance?
Josh: Well, I still have some good friends who are lawyers and I think it’s easier for me than it is for them. One of my roommates from undergrad works crazy hours at a downtown Toronto firm so my work-life balance is a lot easier than that but it’s different. It’s more on and off. When I’m in Columbus, I have a lot of time with my friends and family but when I’m on the road, it’s a little more difficult. Then again, the season is only 6 months long and then I’m back home.
Cristian: Do you have any advice for students who may be interested in a career in sports after law school?
Josh: I have some advice on that. I would say the biggest thing is to follow your passion and know what you want to do. It’s great to say “I want to work in sports” but what exactly do you want to do in sports? What do you want your job to be? Plot out the different points along the way and get to know the people who will help you reach each of those levels or who will at least give you some advice on how to achieve what it is you want to achieve. If you’re a young lawyer, really focus your attention on where you’re headed and who you can learn from that will help you achieve your goals. When I was in law school, I didn’t look for just any sports agency to intern with nor did I look for opportunities with the Denver Nuggets. I got to know the hockey people because those are the people that are going to help you figure out what to do next.
Cristian: What kind of skills do you think are important if you want to find success in the hockey world?
Josh: I really think analytical and strategic thinking is a huge part of it. In law school, you learn how to craft arguments, draw parallels, distinguish things, write persuasively and I think those skills help you as you go forward. But at the same time, you’re also going to have to learn other skills and become more well rounded. Nowadays, it’s difficult to get in just as a lawyer. Last year, we hired someone to be our analytics expert who was a recent law school graduate. He uses his legal thinking to craft analytical arguments. This is the new wave of getting into hockey, through the analytics side. You don’t have to be a data engineer or a computer scientist to do it. There’s a lot of value in people who can craft analytically inclined arguments and I wish we had more of them within hockey organizations. A JD degree is a degree that opens up so many doors for you professionally.
Cristian: If you could go back to a time you were a law student, knowing everything you know now, would you have done anything differently?
Josh: Honestly, no, not a thing because things have worked out well for me. Had I done things differently, perhaps I wouldn’t be where I am today. Maybe one thing I would have done differently would have been to get involved with Kurt earlier than I did. But in the end, I appreciate the fact that my first year of law school was completely devoted to being a law student.
Cristian: How has COVID-19 impacted the state of the profession?
Josh: With COVID going on, it’s hard. If everything is remote, what kind of experience is that for interns who fought hard for a chance to succeed in a field they’re passionate in? I think it’s important if you’re offering someone an internship a real opportunity to learn and further their career. I don’t envy anyone looking for positions right now. Hockey is such a people business. We have had a few interns that have gone on to full time careers in the NHL and a big part of that rested on the quality of their characters. It’s hard to recommend or provide insight on a potential employee that you only know remotely. But this will hopefully all pass and we’ll get back to the way things were at some point.
*I would like to extend my thanks to Josh for taking the time to provide what I found to be valuable information and advice.*