Derwin Webb: From the basketball court to family court

I sat down for a remote conversion with former Louisville basketball star and current Judge, Derwin Webb.

Judge Derwin L. Webb is the first African-American man to serve as a judge solely in Louisville’s Family Court in the history of the Commonwealth of Kentucky. He was a beloved Cardinal from 1988-1993 and was elected Louisville basketball team captain during his senior season.

Derwin Webb came to play for the Louisville basketball program only a few years removed from a second national title, though he was courted by other schools to play basketball. What many don’t know is that he also excelled on the gridiron, for which he was also recruited.

Perhaps Webb’s greatest triumphs, however, came long after his time as a Cardinal. The more we spoke to one another, the better understanding I had of just how far he has come. Obstacles and setbacks never shook him.

Becoming comfortable being uncomfortable

“I grew up in a segregated community. Have you ever heard of the Brown vs Board of Education in 1954? It talked about desegregation of schools but it did not make its way to Indianapolis until about 30 years later when I was headed into 6th grade,” Webb said.

At an early age, Webb was thrust into the unknown.

“School-mandated bussing started, and I was bussed 30 minutes away across the county. For the first time in my life, I was interacting with people who did not look like me,” Webb explained.

Needless to say, it was quite a unique environment for him. “I was put into the advanced program. It was tough for me when I first got there, because I wasn’t black enough for the black kids and I wasn’t white, so I kind of felt like a kid that didn’t have anyone to go to,” Webb said.

Sooner or later, Webb found a way to make his surroundings more comfortable.

“I was smart and athletic; it wasn’t until athletics started that I was able to showcase my skills, and that was when I started to gain acceptance from everyone because I was a good athlete,” Webb said.

It was around this time that his recruiting process started to gain momentum. “I was going to different basketball camps starting in my 8th grade year. (Louisville) used to send out letters saying ‘we noticed you at a camp, etc. I played on one of the top AAU teams in the state, so that’s how they noticed me,” he said.

From the Circle City to the River City

Although he was from “Nap Town”, he always had Louisville on his radar.

“My brother-in-law is from Kentucky, so what I knew about college basketball at the time was Louisville. Even though I was an Indiana kid, I always loved Louisville,” Webb reminisced.

Of course, Louisville had him on their radar as well.

“The first college letter I got came from the University of Louisville. I was a freshman in high school. I thought, ‘that’s the place I want to go’,” Webb said.

However, Webb almost didn’t end up at Louisville. “My high school basketball coach had a good relationship with the coach at Iowa State. I had verbally committed (there),” he said.

Webb was sold on playing for the Cyclones, but he had to close the deal with his parents.

“I told my parents what my decision was and they told me I had made my decision prematurely, and in order for me to go, they’d have to see the campus for themselves,” Webb said. “So we drive out to Ames, Iowa, which is 9 hours away. The coach greeted us with pleasantries and asked my mom ‘how was the trip?’..my mother’s response was ‘my son is not coming this far away’.”

Webb’s mother and father always instilled an awareness of personal responsibility in him.

“I had to be ‘the man’, as my parents would say, and call these different coaches and tell them I was opening up my recruiting process again,” he said.

Denny Crum’s program needed no introduction as far as Webb was concerned.

“The recruiting process with Louisville was great because they were a couple years removed from a national championship. Plus I was always interested in law school and I knew they had a reputable law school,” Webb said.

Again, Webb was met with adversity, and wanted to silence the haters.

“The one thing that intrigued me the most about Louisville was that people told me I could not play here, so it was a challenge to me because they had great athletes. If I wanted to prove to myself that I could compete, I should attend a school like that,” he said.

At first, Webb really just wanted a chance to feel the Hall of Fame coach out.

“As far as Coach Crum, I attended a couple practices without him knowing I was coming because I wanted to see what he was like outside of the recruiting process,” Webb said. “One thing i noticed about him was even when he was upset, he would never swear at his players.“

This went a long way for Webb, who was raised by two level-headed parents.

“He may let them know how he felt, but he would never say anything demeaning. He always treated everyone with respect no matter if they were the star of the team or if they were the last player on the bench,” Webb said.

There was much Webb could learn from Crum.

“Every time I was around him, it was always a teaching moment or a life lesson, not necessarily about something on the court, and I took that to heart. He reminded me of my father. Coach Crum has to be top 5 (all time greatest coaches). What he did in the 80s, and how he was able to be competitive throughout his 30 years as a coach,” Webb said.

Establishing a home away from home

As much as we love to talk about culture here in Louisville, a lot of times we leave out the type of culture that Crum instilled here in his coaching tenure.

“The reason I chose Louisville was bc it felt like home,” Webb said.

Sounds familiar. A family style environment.

“(My closest friends on the team) were Everick Sullivan and Cornelius Holden. Those were two of the guys I came in with. There were a couple of older guys that kinda took me under their wing. When I first got there Kenny Payne was a big brother to me but I probably hung around Craig Hawley and Felton Spencer more than anyone because we had the most in common,” Webb said.

Upon his arrival at Louisville, Webb was already befriending standout players.

“Craig and I played against each other in high school and he hung around Felton all the time so I was kind of like the 3rd wheel,” Webb laughed.

For as much fun as he was having, there were also common college kid hiccups.

“The team bus would pick us up and take us to the game because we had to be there by a certain time. This one time I remember that I had overslept and I missed the bus, so I had to drive my car over to the game,” Webb said. “I remember I had been playing well, and I was supposed to start that game. So I drive over to Freedom Hall and I get to the gate and the parking attendant would not let me in.”

Webb could not believe his ears.

“I was telling the parking attendant ‘I actually play’. He said ‘show me something that says you play’. I said ‘I don’t have anything on me’. He said ‘well sir, you could be John Doe for all I care, but I can’t let you get in’,” he said. “I’m like, ‘sir, I play’. He said ‘I don’t care, you weren’t with the team, so you have to pay the $5 (admission).’ It may have been one of the first times in history that a college player actually had to pay to get into the game he or she was playing in,” Webb said.

Off the court, Webb’s resilience remained intact through the gauntlet.

“My journey to be a judge had its ups and downs but everything I’ve done in life has led to something else,” he said. “After my first semester, I was dismissed from law school because I did not do well. I didn’t pass the bar (exam) the first time. But as you look through my history there were many setbacks.”
This was entirely accurate.

“I got redshirted my freshman year, and it was the first time I ever had to sit out. I was a good football player in high school and I was actually recruited to play at Notre Dame. It’s just funny that Notre Dame ended up winning the national title my freshman year while I was redshirting at Louisville. It was a soul searching year for me,” Webb said.

Preparing for life after basketball

Through the fog, Webb continued to apply his values and work ethic into every facet of his life.

“I saw it as I had to work harder because there were people better than me. I used that same mentality in law school,” he said. “When I came back after sitting out that year, I did better because I knew what to expect. Same thing with the bar.”

Webb always learned from his setbacks.

“After studying and understanding, I did better. My time at Louisville, listening to Coach Crum, listening to all the life lessons – you may lose the game, but you don’t have to lose in the game of life,” Webb said.

He kept his feet churning.

“I went to be appointed judge two times before I actually won. The first time in 2012, the governor chose someone else, and in 2014 I ran thinking that name recognition could help me some, but I lost that election. I could’ve easily gotten discouraged to never do this again until another opportunity came up and I put my best foot forward. I remembered the mistakes I made in the past, and the rest is history,” Webb said.

A much wiser man now, Webb gained his wisdom from his pitfalls.

“You can’t have success without failures along the way,” he said. “Every experience I’ve had has led me to become the judge I am today. I think I’ve experienced everything a judge could experience.“

As a former Louisville player, I was curious to see who Webb had his eye on from this year’s roster.

“I’m a David Johnson fan. I like his game. I like how he plays. I think as he goes Louisville will go. He’s the main cog in the wheel to make this team go,” he said.

After everything he has achieved, in the Louisville community he has transformed from a notable role player on Crum’s teams to an elected Judge Derwin L. Webb. He’s been fighting and overcoming obstacles his whole life.

“Don’t give up, don’t ever give up, and don’t give up on yourself. I wasn’t supposed to be here. I was seriously considering leaving and going to play football for (Notre Dame). But I’m happy with the decision I made, and I’m glad I stayed,” Webb said.