Kylie DeWees (’17)
Marketing
A native of Marion, Iowa, Kylie DeWees (’17) chose Loras because it offered the opportunity to stay close to family while continuing her tennis career. The College’s strong alumni network, faith, and welcoming community made it an easy decision.
Although she arrived at Loras unsure of her career path, Kylie quickly discovered the value of a Marketing degree and the flexibility it could provide. She graduated in just three years while balancing a demanding schedule that included being on the women’s tennis team, writing for The Lorian, participating in Duhawk A Cappella, and excelling in the classroom.
Along the way, a series of conversations with mentors and classmates helped shape her future. Faculty members such as Dr. Eric Eller, who led her mission trip to Haiti, and her tennis coach, encouraged her to think beyond the traditional careers she associated with sports. Through their guidance, Kylie began to realize that sports organizations needed professionals in many different roles, including attorneys.
“Little conversations eventually add up to a certain moment, and then you take the leap,” Kylie reflected.
After graduating from Loras, Kylie continued her tennis career on a full-ride tennis scholarship at Minnesota State University, where she earned a master’s degree in Sports Management. Initially, she envisioned a future in athletic administration, but her growing interest in sports law led her to pursue a Juris Doctor degree at Barry University School of Law.
Today, Kylie serves as an attorney for the Chicago Cubs and Chicago Stars FC, where she handles a wide range of legal matters, from marketing and corporate partnership agreements to negotiating event contracts and helping create memorable fan experiences. As a lifelong Cubs fan, being able to contribute to an organization that means so much to the Chicago community is especially rewarding.
“I love the people I work with and the opportunity to help create the best possible product for our fans,” she shared.
Outside of her legal career, Kylie continues to pursue another lifelong passion: music. A singer-songwriter since age 12, she performs regularly throughout Chicago and has released music on streaming platforms. Her time in Duhawk A Cappella helped her develop confidence in her unique voice and fostered a love of performing that continues today.
Most recently, Kylie was recognized as one of Windy City Times’ 30 Under 30 honorees, an award celebrating young leaders making a difference in their communities.
Reflecting on her journey, Kylie credits Loras with giving her the confidence to explore possibilities she never imagined. The College’s liberal arts foundation encouraged her to think broadly, learn from different perspectives, and pursue opportunities beyond a single discipline.
“Loras gave me a broad understanding of what I could be doing,” Kylie said. “Taking classes outside of my major and having that holistic approach helped me in ways I still see today.”
From once dreaming of being a Harlem Globetrotter, to competing on the tennis court, to now working as a professional sports lawyer, Kylie’s path has been shaped by curiosity, mentorship, and a willingness to embrace new opportunities as they came.
Congratulations, Kylie!
