From mock trial to Stites & Harbison: Louisville lawyer wins 2023 Trailblazer Award

For the last 20 years, Demetrius Holloway watched people he respected and admired receive the Justice William E. McAnulty Jr. Trailblazer Award — including Judges Ernie Jasmine, Janice Martin and Denise Clayton.

But the employment lawyer at Stites & Harbison PLLC was amazed to find out he was joining their ranks by winning the 2023 award.

"I was surprised," Holloway said. "There have been a bunch of people I really respect obtain this award and all super-deserving. Many of them had a much harder road than I did."

The award, given by the Louisville Bar Association, recognizes those who "have made exceptional efforts to promote racial and ethnic diversity within the legal profession" and is named after the first Black person to serve on the Kentucky Supreme Court.

When Holloway found out he was nominated, he knew he was going to have to skip his next LBA diversity committee meeting.

"I'm not going to vote on something I'm nominated for," he said, smiling.

Instead, he went to the company holiday party, socialized with friends and even sang Prince's "Purple Rain" on karaoke.

Before the end of the day, the committee had selected him as the award's recipient. He is set to accept it at the Trailblazer Award Ceremony later in February and is "honored."

"I didn't do anything to try to get an award," he said. "But I've always been trying to be part of the diversity committee and a part of this spreading of knowledge about our community, our culture, and how we are also doing well in the legal field."

Finding a love for the law in mock trial

Holloway, better known to friends and family as "D" or "Man," fell in love with law in a makeshift courtroom at Central High School.

When he attended Central, there were four different tracks to pursue. Out of computer science, allied health, business and law and government, he chose the latter.

But it wasn't because he was interested in the law — at least, not yet.

"A kid that age in the '80s ... everything was about government," Holloway said. "It was the Cold War, "Rocky III," it was the Russians vs the United States, it was all that kind of deal."

And then Commonwealth Attorney Ernie Jasmine came to speak to his class. Holloway watched his presentation and was in awe.

"I was like, 'Man, this is interesting. I think I'm gonna try that,'" he said. "So that's what I did."

Through the program, Holloway participated in a mock trial competition. He was one of two students who acted as the lawyers.

"We took that classroom, and we put wainscoting around the baseline and made a jury box so we could do our practices," he said. "Then we put a little podium thing on top of the table and somebody played a judge. We just practiced opening statements, cross-examination, stuff like that."

One of the mock trial coaches was Kent McElwain, a partner at Stites & Harbison. At the end of the program, McElwain asked Holloway if he wanted to co-op at the firm.

Before then, he didn't often venture downtown from his home on Madison Street in western Louisville.

"We might come down (because there) used to be the Kentucky Theater. ... Walgreens would have hot plates," he said. "But that would be rare. It was cool to be coming downtown. I felt like I was a part of something."

Holloway has been involved with the law firm ever since, from making photocopies as an intern to doing a summer clerkship as a University of Louisville law student to becoming a partner.

He has been at Stites & Harbison since 1991.

'We should always hope that it's better for people behind us'

Holloway was drawn to employment law because it is "real people stuff," he said.

"(It's) how people have been treated fairly or unfairly," he said. "And not just defending that or challenging that, but also creating policies on how you do things the right way."

It seemed more human than the other kinds of law he had been considering because it helps get people "to a place where they can coexist and work together easily," he said.

And over the last few years, this sector of the law has exploded because of COVID-19.

"This type of thing was really challenging," he said. "How do you go about (work) if you can even maintain a workforce? Are you putting people in jeopardy? How (do you) make sure people will be safe? How do you make sure people are following the guidelines, wearing masks or whatever? Now, you're juggling, 'OK, somebody's got a religious belief, and they don't want to take a vaccine,' or they have personal beliefs about certain things."

It was challenging, especially because the situation was so new.

"It was scary, but interesting," Holloway said. "I hadn't seen anything like that since I've been alive."

And through it all, Holloway continued his work — both within Stites & Harbison and outside it. He has been a member of Stites & Harbison’s diversity committee since its inception in the early 2000s and now serves as a co-chair.

As he continues his work on the committee, he hopes to see "more and more people, whether it be women, LGBTQ (people), men moving into different areas of the law, in law firm management, in law firm leadership and just being public figures in the community," he said. "(When) children see people that look like them, that came from where they came from, or have the same type of career aspirations, it gives you hope like, 'Oh, I can do that.'"

Holloway is also a board member for the Louisville Urban League and Junior Achievement of Kentuckiana. In his spare time, he takes on pro bono cases through the Legal Aid Society and has even made a couple of trips back to his old high school.

Once the student in the mock trial competition, Holloway has gone back to watch a new generation compete — in the very same classroom with the wood paneling that makes it "look like a real courtroom."

He has advised the mock trial students — just like McElwain advised him — and worked with other young people through Junior Achievement.

"Whatever was poured into me to help me will hopefully help somebody else," he said. "We should always hope that it's better for people behind us, instead of just what's in front of us."

Reach reporter Eleanor McCrary at EMcCrary@courier-journal.com or at @ellie_mccrary on X, formerly known as Twitter.

This article originally appeared on Louisville Courier Journal: Demetrius Holloway wins Louisville Bar Association Trailblazer Award