For many attorneys and law students aspiring to use their legal degrees to work in the sports industry, an in-house position with a professional organization is considered the peak of an arduous climb to the top of the sports law world. Oftentimes, legal positions in some of the mainstream sports in America, namely football, basketball, and baseball, are typically those that are sought after by sports enthusiasts in the legal world. Nevertheless, due to the exponential growth of its popularity and the constant expansion of its professional leagues, the path toward in-house positions in American soccer has never appeared more open for those aspiring to work within the beautiful game. As a law student who ultimately hopes to attain an in-house counsel position within professional soccer, I wanted to learn from those who are currently in positions in which I and several others passionate about the intersection of soccer and the law aspire to be. In that spirit, I have decided to start a process that I wanted to document by way of Conduct Detrimental to share with all who are interested – an interview with a member of the legal counsel at every MLS club.
From these interviews, I hope to be able to provide insight into the nature of legal counsel positions in professional soccer. And at the end of this process, I hope that we will all be more knowledgeable on what it requires to successfully convert our greatest passions into a dream occupation.
For this interview, I was fortunate to speak with Kylie DeWees – Staff Attorney at Sporting Kansas City (KC). A graduate of Minnesota State University and Dwayne O. Andreas School of Law at Barry University, Ms. DeWees’ first involvement within MLS was as a legal intern for Orlando City SC before transitioning to Sporting KC in November 2021. As well as serving the legal department for Sporting KC, Ms. DeWees spoke before the Kansas legislature and successfully advocated for a change in Kansas child protection laws during the summer of 2023. The conversation I had with Ms. DeWees was incredibly insightful, and it was amazing to get to speak with her. Finally, this conversation represents Ms. DeWees’ individual views and opinions and does not purport to reflect the views or opinions of Sporting KC or MLS. With that said, here is the interview with Sporting KC Staff Attorney, Kylie DeWees:
1. BG: Tell us a bit about your story – what led your interest in working in-house within soccer to develop and the career steps you took that eventually placed you in your current position.
KdW: First off, it’s taken many villages of people to get here, so I will try to remember as many of those who have helped me as I can! I grew up in Iowa without the ability to cheer for very many sports teams at home. In fact, one of our biggest teams is the Cedar Rapids Kernels (like the corn!). I grew up playing sports, specifically basketball and tennis, and I eventually went to Minnesota State to play tennis in college while also studying to receive a Master’s degree in sports management. During that time, I met with the assistant athletic director to resolve a certain issue with my scholarship to the school, which eventually worked its way to the CFO of the university. It was in this specific situation that I first realized the power of advocacy and the power of contracts as important legal documents. Actually, the assistant AD appreciated how I advocated so much that he asked me to be his graduate assistant in compliance. I worked in this position throughout the following year, and it helped inspire my interest in working in sports law. While working in compliance helped inspire this interest on a professional level, there were also personal motivations for my interest in sports law. When I was a child, I suffered from some traumatic events related to one of my former coaches. From this terrible experience, I was driven not only to work in sports to gain justice for others within the industry but also to reform state laws to help better protect children in sports. All of these factors led me to attend law school and specialize in sports law. I chose to go to law school at Barry School of Law in Orlando, Florida to open myself up to more opportunities in the sports industry. After my first year of law school, though, the COVID-19 pandemic hit, which had scary implications for me trying to find my first summer job. Thankfully, I had previously met with a criminal defense attorney in Florida who had represented some major sports clients, and I was able to secure an internship with him that first summer. In my second year, I applied for the legal internship with Orlando City SC. Unfortunately, I didn’t get it on my first attempt, but I was super grateful to have gotten the position after applying for it a second time. Having people at Orlando like Aurusa Moosani and Caesar Lopez as mentors were invaluable for my progression as a future in-house attorney. Heading into my final year of law school, I was informed of a contract administrator position with Sporting Kansas City. After speaking with my mentors at Orlando City about the opportunity, I decided to take it with the additional stipulation that I would become staff attorney contingent upon passing the Bar Exam. Thankfully, I was able to pass the Bar, my title changed to Staff Attorney, and now I’m here.
2. BG: What does a typical workday look like for you as Staff Attorney at the Sporting KC?
KdW: No two days are the same – I’m sure you’ve heard that quite a lot in your other interviews! But something unique about Sporting KC is that we are completely in-house – we own our stadium, we have our own in-house events business, and we are able to operate with a lot more control by being our own concessionaire. More liability comes with that, so we have to assist with a lot of additional agreements that you would not have if you were not your own concessionaire. In terms of how a typical day would look, though, one of my mentors, Dan Werly, SVP, COO of the Tennessee Titans, always brought up doing your tasks in the morning and setting up meetings in the afternoon. While it’s not always easy following that schedule to a tee, I try to check off many of my daily tasks in the morning, whether they deal with sponsorship agreements or longer-term goals, such as tasks relating to club policies. After that, I’m able to sit down in the afternoon and conduct the meetings that I need to have to ensure everything is operating smoothly from a legal perspective.
3. BG: If you could list three of the most important skills necessary to work as in-house counsel for an MLS club and provide a brief explanation for their importance, which skills would you choose?
KdW: For in-house counsel specifically, I would say that interpersonal skills have to be super strong. Many assume that transactional work is quite introverted in that the attorneys seemingly do their work behind a shell, but specifically within MLS, you’re working with every department – corporate partnerships, finance, marketing, ticketing, and the list goes on. You need to be able to collaborate with each department, and that may look different depending on the department. You have to be able to communicate with different types of people and know your audience. Working with an MLS club allows me to work with diverse group of professionals every day. Another important skill is empathy. Having empathy on the job is really important because you never know what someone is going through in their day to day. People will respect you more when you give them a higher level of empathy, and tasks that need to be done will be completed faster when the collaboration is meaningful for both sides. Finally, I would say the ability to set boundaries or expectations with your colleagues is invaluable. If you can do the first two skills well, this last skill falls into place. When you respect people and they respect you, it’s easier to set boundaries with your capability to say when you’re able to get tasks done. And your colleagues will respect your ability to get things done in turn. Everything just works out better when you can communicate to others what they can expect from you.
4. BG: What is one piece of advice that you could offer about the industry to law students that you wish you were given when you were in law school?
KdW: I would probably tell law students this: everything will be okay. A lot of law students who aspire to become in-house sports lawyers are driven, ambitious, and they want to press on to the next accomplishment. To that, I’d probably tell them to slow down a bit and to realize that everything will indeed be okay. It’s tough because you are studying for classes, then studying for the bar, then looking for a job, but slowing down and enjoying the time that you spend with those around you in law school is incredibly important. You’re not going to get that time back, so you need to make the most of it while you have it. Another thing that I would say is that everyone’s path is different. A lot of law students want to come work in-house immediately after graduation, but working at a law firm first often yields the same successful result. One of my colleagues, Andrea Kimball, worked at a law firm in San Diego before coming to work with SKC. Also, some of the most successful people I know in this industry worked in a law firm first before transitioning in-house. Hopefully, that should give some law students ease that their careers are not doomed if they do not land the in-house job they want right after graduation. There are many different paths to achieve success when trying to break into the sports industry.
A very special thank you to Kylie DeWees for her time and for her contributions to this article. She can be found on LinkedIn at Kylie DeWees.
Bryce Goodwyn is a 2L at Regent University School of Law and Editor-in-Chief of Conduct Detrimental. He is a member of the Regent University Law Review and ADR Board, and he also serves as an executive member of the Conduct Detrimental Law Student Board. He can be found on Twitter @BryceGoodwyn and LinkedIn as Bryce Goodwyn.