From One Court to Another

Former college tennis player Regan Osborn is taking on competition in a new kind of court as a second-year law student at the University of Virginia School of Law.

At UVA Law, Osborn is a junior editorial board member of the Virginia Journal of Criminal Law and a participant in the Innocence Project Clinic. She was also 1L representative for the Virginia Law in Prison Project.

Osborn, a first-generation college student from South Shore, Kentucky, earned a bachelor’s degree in sociology from Shawnee State University, where she competed for the women’s tennis team.

In our occasional series “Star Witness,” Osborn discussed how sports prepared her for law school and why mock trial has been her most rewarding experience at UVA. 

Tell us something about your life before law school.

I’m a KJD [kindergarten straight through to J.D.] so my life before law school was … more school. But whenever I wasn’t studying or working, I spent a lot of time on the tennis court. In some ways, I think college tennis prepared me more for law school than anything else. I learned that although a strategy may be great and the execution pristine, you sometimes still get burned on the baseline. But this just gives you an opportunity to learn for the next point. The “fail forward” mentality I learned from tennis has transferred well into law school. Anyone who knows me knows I’m definitely still failing forward when it comes to cold calls!

Why law school?

My faith is important to me, so I wanted a career that would allow me to serve in a way that truly makes a difference in the world. For a while, I had my heart set on becoming a police officer. But studying sociology and criminology, I realized just how intertwined the law is with societal issues and thought I could make a bigger impact on the legal front. I realized becoming a public service lawyer would allow me to positively affect the world of every client I interact with by helping ensure their voices, their livelihoods and their dreams are well-represented. When people feel as if they have no one in their corner, I want to be there reassuring them that they matter and someone cares. Becoming a public service lawyer will allow me to do that.

Describe your most interesting law school experience.

Competing in the [mock trial] 1L Cavalier Classic Tournament. As a first-generation college student, I came into law school with limited legal knowledge and even less familiarity with courtroom procedures. Because of that and some introverted tendencies, I didn’t think mock trial was within the realm of possibility for me. But some of my section-mates decided to go to an information session, and I heard there would be pizza, so I decided to check it out. In that meeting, and all throughout the training process, I met other students who welcomed me with open arms and shared all they had learned about trial advocacy. Eventually, I was assigned to a team and matched with [Judge Advocate General’s Legal Center and School] coaches who helped us prepare for the tournament. It was in those early morning practices that left us running to make it to class on time — and in the late evening practices where we learned how in the world you move something into evidence — that I finally discovered a sense of belonging not only at UVA Law but in the legal profession overall.

What’s something your classmates don’t know about you.

Probably that I’m a triplet! I have two sisters who are both in graduate programs right now. One is becoming an occupational therapist, and the other a licensed mental health counselor. Between the three of us, I’m hoping our family will be well taken care of in the future!

What’s next for you?

Right now, I’m undecided between prosecution and defense. I interned at a local prosecutor’s office this summer, and it was amazing because they fully embrace the idea of progressive prosecution. But I still want to explore public defense, so I’m planning to intern at a public defender’s office in West Virginia this summer. Regardless of which side I end up on, I’m hoping to use my law degree to foster a justice system that sees humanity first and everything else second.