Simpson is a dedicated educator, coach, and lifelong athlete with a deep-rooted passion for basketball and player development. His competitive journey began at North College Hill High School, where his standout performance on the court earned him both All-Conference honors and a selection as a District All-Star.

Following a remarkable high school career, Kenny took his talents to Mount St. Joseph University. Competing for the Lions from 2015 to 2019, he became an integral part of a championship culture, contributing to two conference championship teams during his collegiate tenure.

Basketball excellence runs in the Simpson family. Kenny is the proud grandson of Kenneth Simpson Sr., who was an honorary member of the historic 1964 William Lincoln Grant High School regional championship team—a legacy of pride and community triumph that Kenny carries with him today.

Since 2023, Kenny has served the Covington Independent Public Schools district as both a professional and a coach. Bringing his extensive playing experience and champion mindset to the sidelines, he is fiercely dedicated to mentoring student-athletes, instilling character, and building a premier athletic program that honors the region's rich sporting tradition.