Derwin Webb, Esq.
Derwin Webb, Esq.

Derwin Webb, Esq.

Attorney, judge, former Division I athlete, and leadership speaker on hazing prevention and responsible decision-making.

A first-generation attorney, Derwin L. Webb, Esq. was born in Indianapolis, Indiana, but later moved to Louisville where he has lived for more than twenty-five years. A former standout basketball player at the University of Louisville for Hall of Fame basketball coach Denny Crum, Webb was a captain his senior year, and earned the respect of his peers both on and off the basketball court. As an undergraduate, he was elected as a senator in the Student Government Association. In this role he represented the interests of the student population and discovered the importance of public service. He joined Alpha Phi Alpha Fraternity, Inc. After receiving his B.S. in Political Science, he attended the Brandeis School of Law at the University of Louisville. Upon graduation, he began his legal career with the prestigious law firm, Stites & Harbison, where he learned all aspects of business and corporate law. He then returned to his alma mater to work as an Assistant Athletic Director where he supported the athletic department in areas of compliance, academics, and diversity. He was appointed by the president to serve on the University’s Commission on Diversity and Racial Equality, the president’s chief policy advisor on issues of diversity. He also served on numerous non-profit boards dedicated to improving the lives of individuals within the Kentuckiana region. This work earned Derwin the Business First “Forty Under Forty” Award for outstanding Louisville young professionals. Derwin’s presentations are designed for learning and reflection and do not involve legal advice or commentary on pending or actual cases. Any views expressed are personal and do not reflect the views of the Kentucky judiciary or any court.

  • Contact Speaker information below

  • 3 Presentations

  • 1 Videos

Contact Info

Email: derwin@greekuniversity.org Phone: 516-642-3108 Social Media Links: Click to follow me on Instagram To book Derwin Webb, Esq. for your campus or conference: bookings@greekuniversity.org

Presentations

PRESENTATION: The Trial of Hazing: A Campus Courtroom Experience

What if you could step inside a simulated courtroom to better understand how a hazing tragedy can unfold — and how it can be prevented? The Trial of Hazing is an interactive, educational program designed to help students explore the ethical, leadership, and decision-making failures that can lead to hazing-related harm. Rather than observing from the sidelines, participants actively engage in a hypothetical, mock courtroom simulation based on widely reported public scenarios. The program is facilitated by Derwin L. Webb, Esq., a first-generation attorney and former Division I basketball player, who guides participants through the structure and process of a simulated trial for educational purposes only. PROGRAM FORMAT Participants are randomly assigned roles commonly found in a courtroom setting, including:

  • Prosecutor
  • Defense attorney
  • Organization members
  • University administrators
  • Family representatives
  • Law enforcement
  • Jurors Through this structured simulation, participants engage in:
  • Opening statements
  • Witness testimony
  • Closing arguments All decisions and outcomes are determined solely by the participants as part of the learning experience . LEARNING EXPERIENCE The program concludes with a guided debrief focused on:
  • Lessons learned from the simulation
  • How breakdowns in leadership and accountability can escalate harm
  • The importance of intervention, ethical decision-making, and personal responsibility
  • Practical strategies to reduce risk and prevent future tragedies This is not a lecture. It is an immersive educational experience designed to encourage reflection, discussion, and responsible leadership. LEARNING OBJECTIVES
  • Understand the Ethical and Legal Consequences of Hazing At a high level, participants examine how hazing behavior can result in serious consequences, including criminal exposure, civil liability, organizational sanctions, and long-term personal and institutional harm. The discussion emphasizes general legal principles and ethical considerations rather than specific cases or legal advice.
  • Build Empathy and Perspective-Taking Participants are encouraged to consider the experiences and perspectives of all individuals impacted by hazing-related incidents — including families, peers, organizational leaders, and institutions — and to recognize how decisions made under pressure can have far-reaching effects.
  • Apply Leadership and Bystander Intervention Principles Participants identify critical moments where ethical leadership, accountability, or intervention could have altered outcomes. Emphasis is placed on personal responsibility, courage, and proactive decision-making. IMPORTANT NOTICE This program is educational in nature and uses hypothetical scenarios for instructional purposes only. Any views expressed are personal and do not reflect the views of the Kentucky judiciary or any court. This program does not provide legal advice and does not address any pending or actual cases. WHY THIS MATTERS Hazing tragedies do not begin with catastrophic decisions — they often start with small choices, silence, or inaction. This experience challenges participants to examine those moments and to consider what ethical leadership requires before harm occurs.

PRESENTATION: The Power of Persistence: Triumphing Over Failure on the Road to Success

Perseverance in the face of repeated setbacks, such as being dismissed from law school, failing the bar exam three times, and losing elections, requires immense strength and determination. Each of these obstacles can feel like an insurmountable barrier, yet they also offer opportunities for growth and self-discovery. Being dismissed from law school may initially seem like the end of a dream, but it can also be a chance to reassess your goals and reignite your passion for the law. Repeated failures at the bar exam can be disheartening, but they teach the importance of resilience, persistence, and the value of learning from mistakes. Derwin demonstrates that the path to success is rarely linear and that perseverance is key to overcoming challenges. This journey underscores several important lessons:

  • Resilience: Setbacks are not the end of the road but rather a part of the journey; persistence through failure is essential for ultimate success.
  • Growth Through Failure: Each failure provides valuable lessons and opportunities for improvement, pushing you to develop greater skills and knowledge.
  • Patience: Achieving your goals may take longer than expected, but patience and continued effort can eventually lead to success.
  • Self-Belief: Even when others doubt you, maintaining faith in your abilities and vision is crucial to persevering through challenges.
  • Long-Term Vision: Keeping sight of your long-term goals helps you stay motivated and focused, even in the face of repeated setbacks.

PRESENTATION: Game Over? No Way! Building a Winning Life After Sports

The transition from being a high-profile college athlete to becoming a “normal” person after a sports career ends can be both liberating and daunting. After years of intense training, competition, and public attention, many athletes find themselves grappling with the loss of their athletic identity and the need to redefine their purpose. This transition often involves navigating a new career path, building relationships outside of sports, and adjusting to a lifestyle without the structured schedules and constant physical demands. Additionally, former athletes must manage the psychological aspects of leaving the sport, such as dealing with a sense of loss or the pressure to find new success. For student-athletes, this phase underscores several important lessons:

  • Identity Beyond Sports: Developing interests and skills outside of athletics is crucial for a fulfilling post-sports life.
  • Career Planning: Early preparation for a career after sports, including education and networking, can ease the transition.
  • Mental Health: Prioritizing mental well-being during and after a sports career is vital to navigating the emotional challenges of retirement.
  • Financial Planning: Managing earnings and planning for long-term financial security is essential, especially after the athletic income ends.
  • Lifelong Learning: Embracing new opportunities for education and personal growth can help redefine success in life after sports.

Videos

Featured Video

Photos

Derwin Webb, Esq.Derwin Webb, Esq.Derwin Webb, Esq.